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It’s easy to lose Christopher Wallace in mythology. Because he died so young, and left such an impossible body of work, because of legends those who were around him in his brief lifetime continue to tell, his presence has become larger than life in our imaginations. In New York, the places where he lived, where he walked, where he hung out, and where he recorded have become holy places, ordained sites. A belt he wore and once happened to leave behind in an office at The Source took on talismanic properties, passed down from editor to editor through generations of staff at the iconic magazine. He’s the closest thing hip hop has to a patron saint. But his monumental legacy doesn’t come from some godlike, alien greatness, but from his endlessly endearing humanity. 

When we discuss Christopher Wallace as the GOAT, we use all the wrong language and ask the wrong questions . While we debate merits and sample size and Puff, and Faith and Pac, the question isn’t “IS Biggie Smalls the Greatest rapper who ever lived?”, but “CAN Biggie Smalls BE the greatest rapper who ever lived?” If your answer is no — that there just isn’t enough to qualify him among rappers who achieved generational longevity like LL Cool J, Lil Wayne, or Jay-Z — it’s a brief and simple conversation. If the answer is yes, the conversation is equally brief and simple.

Biggie simply presents the most unique, astonishing, baffling body of work we’ve ever had to consider as nerds who live to argue about inane bullshit and rank things. With the possible exceptions of Big L and Big Pun, who didn’t quite put together the formal body of work in the same tragically brief period of time, there’s no career to even compare him to. No other rapper offers such an unorthodox challenge to the question of quality over quantity. So let’s attempt crossing genres to find historical counterpoints. Biggie has slightly older peers in the infamous 27 Club. But The Rolling Stones’ Brian Jones had three albums in a collective — as did Hendrix. Nirvana had three proper albums and a historic MTV Unplugged session. Biggie’s closest musical counterpart in terms of resume is probably Amy Winehouse, a brilliant artist and writer, but she only gave us 25 proper songs, basically the length of Life After Death to assess, before passing on. 

Let’s widen the aperture on the question of greatness itself. There’s no real comparison in sports, with the possible exception of Len Bias, who never got to the league. But as a thought experiment, I’ll present Biggie as a hypothetical athlete: Imagine a rookie who enters the NBA, wins Rookie of the Year, MVP, Defensive Player of the Year, leads the league in points, rebounds and assists, and wins the championship. Then this player comes back the following season, does it all again with Most Improved Player replacing Rookie of the Year, ends the NBA Draft and the salary cap due to its inherent unfairness and labor rights violations, and then dies.

Imagine an American politician who rises from obscurity, runs for president as his first attempt to be elected to any office at the earliest possible age, wins all 50 states in a landslide, solves Universal Health Care, achieves common sense gun regulations, raises the minimum wage to $25 an hour, ends our foreign wars, achieves statehood for Palestine, runs for a second term, wins by a greater margin, packs the Supreme Court, turns D.C. and Puerto Rico into states, abolishes prison and the police, and then dies. 

You have to go far, far afield to find an artist who presents the same knotty challenge. The 19th Century French poet, writer and enfant terrible, Arthur Rimbaud, published an incredibly small body of work in his lifetime, only a bit more than that output was released posthumously, and all of it had a staggering, outsized impact on writing and thought for generations after. He also died 13 years older than Biggie ever got to be.

Biggie’s body of work contains 42 proper songs (depending on how you qualify “B.I.G. Interlude”, considered in this context as a proper song), 36 guest verses (depending on how you qualify his work with Junior Mafia, presented here as guest work), a handful of demos and freestyle verses and interludes, and they’re all relatively perfect. He came into this world fully formed, as brilliant, confident and commanding as a teen rapping in Clinton Hill and Bed Stuy basements and street corners as he was on his final atmospheric mission statement album closers. The margin between his best and worst work is as thin as we’ve ever seen, and the very worst would rank as the absolute best most of his peers in your top 10 could ever muster. 

You’ll see Biggie’s lyrical exhibitions — songs that were exercises in pure spit, with little thought given to the hook or concept or commercial viability — weighted towards the top of this list. But he was also rap’s greatest storyteller and dramatist. He was among rap’s greatest pop musicians, effortlessly tossing off hooks and formal mainstream smashes that were witty, raunchy, and catchy at a time it was very difficult for even great rap songs to connect with national audiences. Aesthetically, he had the greatest voice any rapper ever had. The greatest flow, a percussive semi automatic weapon he fired at the mic like Max Roach beating a snare. He was a gravitational presence no matter how minor his contribution on a track. 

His wordplay wasn’t just clever, communicating his intelligence and eye for detail, he also had a flare for the beauty of language. His first few bars were always enthralling ad instantly seared into your brain. And finally, a controversial take I simply can’t leave out of his resume conversation: Hardcore is partially Biggie’s great lost album, and as a work of creative crime fiction, perhaps his most impressive and imaginative effort. 

The challenge with Biggie comes to breadth. Is it really fair to say a guy who died a few months into his 24th year — with two proper albums in the can — is greater than an artist like his brother and rival Jay-Z, who was three years older than Big and has been releasing, if not great, at least relevant music for the length of Biggie’s entire life? He was notoriously stingy with his brilliance. It’s the dearth of material, the unanswerable questions. Even his tossed off radio freestyles all eventually became album verses, and can you blame him? If you had an immaculate verse people will be reciting for generations, would you really just let it live on a Stretch and Bob bootleg only a handful of New Yorkers had access to during Big’s lifetime? 

The saddest part of this exercise for me is its possibility. We shouldn’t be able to rate every song, all the tossed off appearances and skits and loosies, that the greatest rapper who ever lived made in a readable and coherent internet list. This should be a masterwork of criticism, something that takes a great scholar years of thought and effort and hundreds if not thousands of pages to contextualize and grapple with. But that’s the sad brevity of what Big left behind. 

While that fact is crushing, it’s a testament to Big that it doesn’t diminish just how impossible this exercise is. How do you rank “Big Poppa” above or below the Stay With Me Remix of “One More Chance”? It depends: do you prefer “Happy Birthday” or “Auld Lang Syne”? In many ways, for as aggravating and subjective as any list can be, this is the most subjective. 

Do me a favor and make a two- item grocery list, you’ll have an easier time deciding if “Milk” is better than “Eggs,” than we did deciding if “Who Shot Ya” is better than “Warning.” The variance on this list is staggering. Of course, every opinion is “right”, but it’s perhaps never been more defensible than when trying to make qualitative assessments of Biggie music. He defies consensus and definition like no other artist ever has. 

There’s a little joke I include for my own amusement in these lists whenever I ship them off to Jeff and Martin. I always include the word “Definitive” in the title of whatever bullshit I’m ranking. The idea is making fun of the list itself, of the concept that we can order people, or their art in any lasting and/or meaningful way. I didn’t include that word in this title because even facetiously, the idea that any one person or group of people can make sense of Biggie’s music in a decisive, coherent way is absurd and insulting.

This is not hyperbole, I truly believe for generations, people who love music will approach these 106 songs in awe, in disbelief that an autodidact who couldn’t rent a car on his own was responsible for it all. The meaning of this music, and Biggie’s impact on history, will continue to shift and change shape on the horizon as that horizon falls further and further behind us; but I feel secure that decades from now, it will still be very much on our minds and in our hearts. 

A brief aside on methodology: For a track to make this list, Biggie had to be alive for the recording: nothing posthumous is included; vocal samples don’t count. The murky waters come when considering versions of verses that have variations appearing on unreleased tracks and freestyles; if there was enough significant change, or a multi verse freestyle had a mixture of verse that appeared elsewhere, but was also original content, we included it. We tried to strike a tone of generosity and judiciousness, so completist basement types can feel free to go hammer in the replies, and maybe someday we will update this with your irate “well actually”s. As for how these brave souls made their ranking, was it a question of overall quality of song, Big’s performance on it, what they ate for breakfast and how the song in question made them feel as a result, I can’t say. That is between them and their Gods. 

The greatest artists and writers go beyond the artifice of their creations, creations like the character “Biggie Smalls,” a 70s baby who grew up in a Reaganomic nightmare on St. James Place in the 80s, who was taught nihilism and violence by a society that hated him and actively tried to kill him, until it succeeded. They lay themselves bare. For Biggie, moments like that “I’m sorry” simply exuded from him on his formal songs, in interviews, in skits, they bled through in the margins of the music he made. I love him for his brilliance, but it’s his resilient warmth, his humor, the soul he left for us to revisit when we miss him everyday, but particularly on days like today, that elevates him beyond the base comparisons we fall prey to when doing the yeoman’s work of hopelessly attempting to order perfection. 

There’s this selfish thing we do when artists die, we essentially grieve two deaths, the death of the person, and the death of the art we’ll never get to experience. Most of these artists are strangers to us, and while we pay lip service to the death of the person, it’s the death of the art that we truly mourn. For me, even as a 12 year old floored by the news of his senseless murder, Biggie was the rare artist whose loss as a person hurt me as much, if not more, than unmade art we all lost forever on March 9th, 1997. It’s a loss I suffer anew every time the ghostly track fades out into eternity on his final proper song, “You’re Nobody (Til Somebody Kills You)”.

But the statement made in that song title has never been less true of any great artist in my lifetime. Agree with this list or disagree (even I have my bones to pick), but understand we all embarked on this quixotic mission so today, perhaps, in our small corner of internet rap discourse, we can definitively close the book and say in unison, Rest In Peace Christopher George Latore Wallace, the greatest rapper who ever lived. — Abe Beame

Note to Reader: #106-50 are written by Abe Beame 

*104-106. *R. Kelly- “(You To Be) Be Happy” & “Fuck You Tonight” & *Michael Jackson – “This Time Around“

Unfortunately, we have to open this list with three asterisks; we are running out of art in the world that has aged well, and not even Biggie is immune to the ravages of time. None of these songs “belong” as Biggie’s worst songs. “Fuck You Tonight” in particular, is an exemplary Rap and Bullshit ’90s classic that serves as another article of Biggie’s mastery of form on his kaleidoscopic, genre warping sophomore mission statement, Life After Death.

But in light of the allegations against Michael Jackson, and R. Kelly being a fucking monster, something we all came around to far too late (including after Big’s disciple Jay Z, made two joint albums with him) we could neither properly rank these songs in good conscience, or ignore their existence while staying true to the nature of this exercise. Perhaps a cop out, both in including and effectively excluding these songs from the list depending on your perspective, but this was the consensus. 

103. Lil Kim – “Fuck You”

Grim and dour shit talk at the end of Hard Core on a Junior Mafia reunion, this song qualifies for the list by the slimmest of margins. Big gets on the mic for 4 lines of shit talk in between the second and third verse, but still has enough time to drop the “F” word. It’s here because we are refusing to subject ourselves to the replies that will follow when someone catches this and thinks we missed it. It’s here.

102. “Blazing Chronic“

This might be the slightest contribution to this entire list, even though it’s two half/quarter verses. It’s probably the only song here that feels under considered, potentially even mailed in. It’s difficult to assess whether this was even intended to be a song. It can be found on a Youtube video with Biggie’s “demos” but couldn’t have been a part of the original four track demo tape that got picked up by Matty C in The Source. If anything, it sounds later, closer to the Ready to Die rollout because the audio quality is decidedly better than the demo era tracks, and yet it’s worse than all of those. A confounding document.

101. Lil Kim – “Take it!”

An Interlude in which Cease and Big exchange a crass and horny locker room talk. It’s pretty raunchy and misogynistic, but nothing so bad it would preclude 63 million people from voting for you to be president.

100. Bandit – “All Men Are Dogs (9 MCs mix)“

An impressive array of mid tier tri-state guys got together for a misogynistic romp, including Grand Daddy I.U., Mackwell, Positive K, Pudgee Tha Phat Bastard, Raggedy Man, and Snagglepuss. Biggie gets the penultimate verse, just before his friend Grand Puba. This verse has been lifted several times, it notably contains the hilarious assertion that Biggie is, in fact, the father of the son of God. 

99. Luke – “Bust a Nut“

This is absolutely filthy, a particular brand of explicit and very horny rap that X rated MCs like Uncle Luke and Akinyele built careers on in the 90s. As always, Big can rise to any occasion and assume any form, spitting graphic pornography that would make the God Larry Flynt blush. 

98. Toni Braxton – “How Many Ways (Bad Boy Remix)“

This is the worst of Biggie’s R&B remix work, which is to say it’s better than 99% of R&B remixes. It has the feel of one of those industry moves Biggie would often kvetch over Puff dragging him to do early in his career (the song dropped in 1994) in the interest of broadening his fanbase. But Biggie is buried three and a half minutes in and follows a lazily spit early Puff semi-verse, and Big’s verse is even shorter. 

97. Aaron Hall – “Why You Tryin to Play Me“

This verse was repurposed on the abominable “The Ultimate Rush” with Missy Elliot on Duets as well as the equally abominable “The Reason” off Faith Evans’ The King & I. Aaron Hall was a member of Guy, Teddy Riley’s foundational new jack swing act, who were signed to Uptown. As we’ll continue to see going through the bottom half of this list, Uptown connections explain a lot of the early random collaborations (mostly unreleased) Big would end up contributing to. That’s likely the explanation here, but while most everything Biggie ever touched left a digital paper trail, this song has what might possibly be the smallest digital footprint. 

96. “Mumbling & Whispering“

Wrestling with Biggie freestyles is always tricky. Because he never wrote, everything he spit was in a sense spontaneous, and perhaps lent some of the magic to his performances on mic. But most of his verses, from the unwritten one take album verses to radio freestyles, were composed, complicated and fully formed when he delivered them, and would re record in other spots verbatim. This loose, rambling and shaggy “song” recorded in Mister Cee’s basement feels like an exception. It’s still very good, but lacks the laser focus and polish most of Biggie’s verses possess, going as far back as the original 50 Grand demo tape.

95. “Life After Death Intro“

Sneakily one of the most disturbing tracks in Biggie’s catalogue. Life After Death picks up right where Ready to Die left off, with a gunshot and a thud. In the opening moments of the sequel, Puff wrestles with grief at Biggie’s bedside in the hospital as he fights for his life. Further up this list, we’ll discuss how important intros and themes were to the world of Biggie’s albums. This intro transcended the world of the album and captured what must have been close to a real life moment, mirroring Puff at Biggie’s bedside as he fought for his life and just a few weeks before this album dropped. 24 years later, it’s still a tough sit.  

94. 2Pac – “Runnin From Da Police“

This was recorded sometime around 93-94, with the intention of landing on Pac’s Thug Life compilation, then Me Against the World, which never happened for obvious reasons. But over the Easy Mo Bee beat, Big shares his verse with the also deceased Stretch (who has been subsequently accused of being the mastermind of the Quad Studio robbery/shooting in 1994 that led to the Biggie and Pac beef); the sound quality is poor, in spite of being one of only three collaborations on record between the two legends, there’s a lot working against it. 

93. “Money, Hoes & Clothes” (Also known as “If I Should Die Before I Wake,” Unfinished, unreleased version)

Like any full or even partial Biggie verse, this sketch intended for Ready to Die then abandoned made the rounds, showing up on mixtaple/blend God Ron G’s “Stop The Breaks”, a pasted together motley posse cut with Raekwon, Killa Sin, KRS One, and O.C. It next showed up on Born Again, with the song more or less intact, with Beanie Sigel, Black Rob, and Ice Cube verses attached. The original feels very loose and improvised, in need of some tightening, but even this still has a routinely perfect opener and a thematic thread (the crib littered with guns). 

92. “N***as*“

This unreleased cut would eventually be mined by 50 Cent for a hit off the Bad Boys II soundtrack. There are pieces of bars that will re-emerge polished on Ready to Die, but what’s impressive is even this rough outtake could be repurposed as a monster years after Biggie’s death with the Aftermath machine behind it. 

91. “Ready To Die Intro“

We may or may not give Big, Puff, and the Bad Boy braintrust enough credit for introducing a cinematic quality to the rap album. De La Soul innovated the skit, Rza and Wu-Tang had similar themes, sounds, and moods, but let’s say if both groups had a director whose aesthetic they channeled, it was Kenneth Anger. The worlds of their albums were chaotic postmodern composites that threw everything at the wall, and they all stuck to create a shaggy aesthetic.

Bad Boy, particularly on Biggie’s projects, took specific and cohesive cues from 70s blaxploitation biographies of kids growing up poor, and of course, Scorsese and De Palma crime flicks about the resilient rise to power. Ready To Die’s table setter has all these qualities. There’s real production value on display: voice work, a soundtrack, the introduction of a story being told about a ruthless and sadistic character named Biggie Smalls that will unfurl over the course of the next 17 tracks. It is, in and of itself, a great and innovative piece of performance art. 

90. Junior M.A.F.I.A. – “White Chalk Pt. 2” (Guide Vocals)

It’s tricky to quantify exactly how much of the material produced by Biggie’s affiliates can be attributed to him. There’s the suggestion that he wrote the majority of Hardcore, but how much exactly? And then there are reference tracks like this one floating around that give us pretty definitive evidence he not only wrote entire tracks for Junior Mafia, but laid down vocals for them to trace his delivery. It’s fascinating to listen to this back to back with Trife’s actual verse from this Mafia loosie off the Original Gangstas (A 96 Blaxploitation reunion) soundtrack. Trife hits all his marks, and is saying the same words verbatim, but it lacks Biggie’s spark. The man just had magic. 

89. “Fuck Me (Interlude)”

We discussed this in depth in the intro. It’s Big at his self-deprecating best, it’s a great vocal and athletic performance by Kim, it’s a classic game of dozens, it’s quite possibly the funniest moment on Ready to Die.

88. Various Artists – “The Points”

This posse cut off 1995’s Panther soundtrack got an actual video treatment. Big gets the leadoff spot, and it’s always an excellent call letting the guy with the best verse intros in rap history spark a song, but it also probably didn’t hurt that the song was produced by his real life friend Easy Mo Bee. Ostensibly, this track is a symbol of unity featuring MCs from all over the country, but in execution it’s a kind of hilariously scattered and topic-less mess [ed. note. this song should be way higher]. Biggie wins best in show because of course he does. 

87. Red Hot Lover Tone – “4 My N*****“

Today I learned this is actually Tone, as in Tone and Poke, as in the Trackmasters. Tone would play a quietly important role in Biggie’s career, producing “Juicy”, as well as the Trackmasters’ uncredited production on the Stay With Me remix of “One More Chance” and “Who Shot Ya.” This dropped just months after Ready to Die, and was presumably Big returning the favor for Tone’s invaluable contributions to the project. Biggie’s tongue twisting wordplay on this brief verse is phenomenal, and Nas would borrow a snippet for the hook on “Last Real N**** Alive” off God’s Son. There’s also an excellent Buckwild remix of this that’s a must listen. 

86. Pepsi Freestyle

I’m such a sucker for great rappers spitting commercials. Shoes, 40s, cell phone plans, play it three times an hour on Hot 97 and take my money. I don’t even drink soda, and preferred Coke back when I did, but I may just run to a bodega and grab a Pepsi right now. This was something Big recorded in 1997 with DJ Enuff that was dragged out to commemorate Big’s Rock & Roll Hall of Fame induction last year. And, you know, to sell Pepsi. 

85. St. Ides Commercial

Everything we said about the Pepsi Freestyle but with alcohol, so, you know, better. What’s great is this commercial from 95 also uses a line that creeps into the Pepsi freestyle, that he prefers both St. Ides and Pepsi to the “Tastes Great, Less Filling,” which was Miller Light’s slogan. So in a malt liquor commercial, and in a soda commercial he recorded two years later, Big stayed lacing sublimals in his rhymes, and Miller Lite hilariously stayed catching strays.

84. “House of Pain” 

This is nearly as close as this list comes to a “bad” song. It sounds like something recorded in a shower booth, but the Stretch and Pac verses come off like first-draft, generic, one-take disasters (It was initially intended for Ready to Die, but responsibly cut, presumably because it’s bad and wouldn’t have fit at all). Then the clouds part and Biggie starts spitting, and it’s just remarkable. This seems like something tossed off in a dicking around blunt and 40 studio session for everyone else, but he simply had no other speed. It’s why he’s the greatest. He had no autopilot. Biggie plays with tempo and cadence, and the verse has the air of the jaded sadness he brought to his greatest and grief filled songs. 

83. Pudgee tha Phat Bastard – “Think Big“

Big and Pudgee, a Bronx born rapper who ended up making a career for himself as a ghostwriter, went way back (they had previously gotten on Bandit’s “All Men Are Dogs” together). Circa Summer 93, Pudgee was considering whether or not to get on a beat provided by fellow Bronx native and Money Boss Player member Minnesota, featuring a hook from MBP’s Lord Tariq. The beat sampled Donny Hathaway’s “Vegetable Wagon”, which had just been flipped completely differently by Dr. Dre on “Rat-Tat-Tat-Tat.”

Perhaps as a result, Pudgee wasn’t feeling it and was about to pass. At that moment, Big walked into their room at Giant studios. The Tariq hook was pre-recorded and the song’s name, ironically, was already “Think Big”. Biggie loved it and immediately locked in, employing the mystical process of standing in front of a mic and nodding with his eyes closed for a while, something akin to meditation, as he thought through his verse, and knocked out his part in ten minutes. Pudgee quickly changed his mind, and the result is classic subway rattler, a cutting room floor ’80s cop show theme. Biggie goes in, a mix of hard spit and straight faced humor (“N***** is ass out like fat bitches in bikinis”)……… that got lost in the shuffle because they couldn’t clear the sample.

82. “Love No Hoe“

Circa 1991, the teenaged Biggie recorded a four track demo that eventually grabbed the attention of Matty C (Matteo Capoluongo) at The Source and launched Big to stardom. Other tracks on the demo are better known for good reason: they show the ferocity, the dexterity, the alien refinement, as the very first Christopher Wallace rhymes are being recorded. But this is probably the most endearing. If you can get past what was pretty standard tongue in cheek early 90s casual misogyny, which shouldn’t necessarily be excused but perhaps at least understood as rap’s predominant lingua franca unless you were the leather necklace type (Big decidedly was not), Biggie is actually warm and open hearted here.

Seemingly born with that booming voice and masterful delivery, Biggie never sounded younger. He’s the classic precocious New York City scammer that has a worldly confidence despite barely ever traversing outside his borough, who can feed you bullshit, and you know it’s bullshit, and he knows you know it’s bullshit, but through sheer charm and charisma you end up kind of taking the bait anyways. Here, it’s Big trying out his loverman shtick (all feather ruffling Bed Stuy braggadocio you’re supposed to take with a grain of salt), and again, he’s already impossibly close to what will be his “finished form” on his albums in terms of flow, control, and his master storyteller’s eye for detail (his girl buggin because his lips are chapped, indicating cheating somehow(?), gets me everytime), but more than “Microphone Murderer” or “Guaranteed Raw”, the goofy teenager he was shines through here.

81. R.A. the Rugged Man – “Cunt Renaissance“

Tone from Trackmasters was the plug on this one. Tone met RA at Chung King around ’93 before Biggie had really blown up, but by the time they got in the studio to record this, he had. RA’s label was hoping he could replicate the crossover success Biggie had found with “Juicy”, and urged RA to use his Biggie spot to do just that, and RA responded in typical fashion, by delivering the musical equivalent of raw sewage. This is just an absolute grimy, stinking, scratch bombed, underlit dive bar bathroom of a song. It’s evidence that if he wanted, Big could’ve also run in underground circles and given horror-core pervert maniacs like Necro a run for their money. Also, we can listen to this now and be thankful Crustified Dibbs made the decision to change his moniker to R.A. the Rugged Man. 

80. Various Artists – “Flip Dat Shit“

A Biggie verse perhaps better known as the “16 Bar Acapella” freestyle, this posse track with Onyx, Naughty by Nature, and 3rd Eye was supposed to make the Who’s the Man the man soundtrack but didn’t, and wasn’t discovered until much later on a discarded advanced copy. Biggie is practicing classic New York mixtape flow here, hitting references and connecting on punchlines “Like Riddick Bowe.” Other than the fact this soundtrack already featured Biggie’s first great single, “Party & Bullshit,” it’s hard to understand why this didn’t make the cut. 

79. “Can I Get Witcha?”

This was recycled for Born Again, but the original version over a prominent “Apache” sample is far superior. I like this song because there’s a popular narrative that much of Biggie’s commercial acumen was grown by Puff, that Biggie was a reluctant, exclusively hardcore MC who had to be led to pop. This is an instance of Big, early in his career, doing a more formal and pop leaning version of a song like “Love No Hoe”, presumably before he got involved with Puff, and it’s great.

78. Heavy D & The Boys -“A Buncha N*****“

A perfect posse cut from 1992 that has its fingerprints on a few subsequent Big tracks during this early 90s run. It was Big’s first major label appearance, and the first of several collaborations with Uptown artists Puff connected him to. Big loved Hev and even had considered a potential joint album. It was also the first, but not last time he collaborated with his high school classmate Busta Rhymes, who was making his first appearance here as a solo artist. And finally 3rd Eye (Jesse Williams III), the rapper producer who is featured on this song in both capacities, would also pop up on the track or in the credits on “Dolly My Baby” (remix), “Flip Dat Shit”, “Biggie Got the Hype Shit”, and the infamous 2pac collab “House of Pain.” It’s beating a dead horse, I know, but it’s simply incredible how comfortably Biggie holds his own on a track, his first as a signed artist, with legendary MCs he looked up to like Heavy D and Guru, who had years of experience on him. 

77. Neneh Cherry – “Buddy X (Falcon & Fabian Remix)“

A song about Lenny Kravitz cheating on Swedish singer Neneh Cherry’s friend, and his wife at the time, Lisa Bonet. This deserves mention with the best Big R&B guest verses because he is just destroying the pocket here in full new jack swing. He does something great that a lot of 90s R&B songs did where he picks up the narrative of the song and takes makes the opposing argument, voicing the defamed, cheating “Buddy X”, and you’d imagine at some point in an argument, as their marriage was dissolving, Lenny said something to Lisa along the lines of, “The sex was great, but the headaches I can’t take/I think I made a very big mistake.”

76. Da Brat – “Da B Side“

In 1996, Big and Puff were ahead of the curve, jumping on this Brat remix with Jermaine Dupri when there was very little interaction between New York and the South. It was Bad Boy campaigning for pan rap unity at a time it was sorely needed with the East-West wars raging. Dupri would return the favor, working with Kim the same year on “Not Tonight” towards the end of Hardcore (The song is run of the mill mid 90s Dupri butter soft R&B tinged rap, but notable because the next year it was remixed as “Ladies Night (Not Tonight)” an all-star female MC showcase featured on the Nothing to Lose soundtrack).

There had been other New York/Southern collabs leading up to this (Including UGK, Keith Murray and Lord Jamar’s excellent “Live Wires Connect” on the Don’t Be A Menace soundtrack) but this was one of the most splashy for its moment. In the next few years, Raekwon would jump on Aquemini, and Jay-Z would be collaborating with Juvenile, UGK, and Dupri himself, but you could argue Bad Boy opened the door for that cross pollination. Oh, and by the way, the song itself is great. Big is firmly in the smooth/confident “Big Poppa” flow he used for commercial grabs like this, but takes nothing off his fastball. The structure is unusual for a radio hit, with Brat and Big trading bars rather than clearing out so each can deliver a proper verse. 

75. Junior M.A.F.I.A. – “Oh My Lord”

For many, this is the forgotten Big appearance on Junior Mafia’s Conspiracy — as compared to “the hits” (“Get Money”, “Player’s Anthem”, and the “Gettin Money” Remix). It’s so obscure, both of Biggie’s verses make up sections of the infamous Tim Westwood Freestyle re-released on the 20th anniversary of his passing, and many believed their portions to be legitimate freestyled/unreleased material mixed in with verses from “The Points”, “You’re Nobody (Til Somebody Kills You)”, and “Kick In The Door”. Which is a shame, because it’s a great song that features a great, icy Special Ed beat and two great Biggie verses. Who knows who wrote Kleptomaniac’s verse, but who cares? It’s probably the best non Kim or Cease Mafia performance on the album. And literally every Biggie bar here is a quotable. 

74. “Interview/Biggie Speaks”

A bonus track attached to “I Got a Story to Tell” at the end of Disc 1 of Life After Death, this 11 and a half minute conversation is a heartbreaking look at where Biggie’s head was in the lead up to the album. He sounds alternately hungry, disillusioned, disappointed, and hopeful. You can’t pick up the interviewer’s audio (or it’s edited out) so it sounds like Big having a conversation with himself, wrestling with the drama he believed he was finally putting past him, and what must have been enormous pressure to top the perfection of his debut. He talks process and approach to the album, what he saw as his role as an artist, and reflects on the legacy and impact of his beef with Pac. But more than anything else, what he communicates, as always, whether in verse or conversation, is his intelligence, his empathy, his wit, his confidence, his humor, and his warmth. 

73. “Whatchu Want“

An Easy Mo Bee production that was cut from Ready to Die after being deemed “Too Hardcore” for the album. As impossible as that standard seems, when you listen to the song now, you kind of get it. Maybe not that the song itself was “Too Hardcore” in terms of its content in comparison with the multitude of wild shit Biggie spits on his debut, but perhaps its inclusion alongside the rest of the incredibly blue, rough material could throw off the album’s perfect calibration, balancing hardcore and pop. This is because the song is a ruthless Howitzer cannon, and Biggie is in full, breathless “sadistic/savage” mode. In other words, perfect.

The epic drama of “Get Money” is remixed as a pleasant money counting session with the Mafia’s brightest stars. Lance “Un” Rivera and DJ Enuff’s take on the often sampled “Don’t Look Any Further” is one of the best iterations, I particularly love how much of Dennis Edwards’ vocals are left in the margins. All three performances are great. To this day, it’s a fucking jam. 

72. “Playa Hater”

I was listening to this randomly a few months ago when it occurred to me that this is Biggie’s idea of a Naked Gun/Bond theme. It’s lush, orchestral, melodramatic, and hilarious. According to Cease, they were all stoned in the studio fucking around when they made this, which makes a lot of sense. It appropriately contains elements of “Basketball Jones” by Cheech and Chong, and “Hey! Love” by the Delfonics. It’s a glittering 70s soul ballad that got an assist from Ron Grant, who has hosted a long running open mic at the Village Underground in Greenwich Village. The track was recorded at Daddy’s House in Hell’s Kitchen, which just happened to be next to a strip club named Blue Angel where Ron’s Band was rehearsing. They were grabbed on a whim and brought up to lay the track down, which they did in one take.

As we learned in Emmet Malloy’s recent (excellent) Netflix documentary, Big could really sing, so the warbling on display here feels intentional, an in-joke laughing at the very idea of a sweeping ballad in the middle of Life After Death. Even though it’s an insane, howling, stoned concept song that easily could’ve been cut from the album, it makes a kind of sense as a mood piece alongside mature gangster epics like “Fuck You Tonight”, “The World Is Filled”, “Another”, and “I Love The Dough”, among others. Whenever I listen to it, I feel like I’m in a penthouse hotel room with floor to ceiling windows, wearing a linen suit and Gucci shades at night, holding a flute of Perrier Jouet Belle Epoque, looking out on the city glittering below me. This was surprisingly a Hot 97 mainstay in New York for a few years following Biggie’s death.

71. Tracy Lee – “Keep Your Hands High”

You probably had this album if you were in high school in the late 90s, not for this track, but “The Theme,” which was a throwback party anthem and a major hit in 1997, when Tracey Lee’s debut Many Facez dropped. The album was produced by go to Bad Boy Bomb Squad the Hitmen, which perhaps explains why Biggie recorded this verse for Tracy at D&D in December 1996. This means besides his contribution to “Victory,” recorded the day before he died, “Keep Your Hands High” was probably Big’s penultimate recorded performance, and it’s a great one. Biggie always gave more of himself to these one on one collaborations than any other artist. It’s never that he just shows up, drops a verse and cashes the check, there’s always these unexpected little verse snippets, trading bars with the artist, adding ad libs, going above and beyond what any other rapper was doing with their features.

This sounds like a progression from what he was doing only a few months earlier as he wrapped up Life After Death. The punchlines are crisp and sharp as ever, but the wordplay is increasingly dense, the rhymes and allusions becoming more complex. Stumbling upon this on a first listen (the album dropped two weeks after Big died), was like seeing the final, anti-climatic, low budget performance from a dead actor trickle out after they pass. It’s weird, and kind of sad to think, this is it.

69. “Macs & Dons”

Even before he blew up, Biggie was writing and rapping for others, as this is a reference track for an MC named Shelton D, recorded at Gordy Groove studio in 1994. This one is extremely light and fun, perhaps because it’s modeled for another rapper, a lot of Biggie’s trademark menace is absent. It’s absolutely packed with reference and in-jokes as Biggie bops and swings over Fresh Gordon’s very early 90s production. 

68. “Another”

Not a psychologist, but perhaps there’s something to glean from Biggie and Kim’s two full scale collaborations being War of the Roses style he said/she said breakup anthems where murder, jail, or at the very least ghosting forever is very much on the table. By all accounts, Big and Kim had a wildly tumultuous and dysfunctional relationship that lasted much of Big’s adult life, and again, should you be so inclined, there’s a lot of psychology on display both here, and on “Get Money” (Kim has alleged most of the content of this song was derived from an actual argument the two had in the studio that resulted in violence).

More so than the life or death stakes of “Get Money,” “Another” seems to exist in a world closer to this one, albeit one that’s still highly stylized and filtered through a vaseline smeared Scorsese lens. It feels like a kind of cathartic couples therapy session built on both Kim and Big reckoning with the “Can’t live with em” platitude, the conflict between the attraction and repulsion that can come with a volatile relationship gone on too long that both Big and Kim are working through in verse. Kim is absolutely ferocious, and holds her own, remaining Biggie’s all-time greatest sparring partner, give or take a Jay-Z. It’s riveting stuff, which occasionally may obscure how great the actual song is.  

67. Mary J. Blige – “What’s the 411? (Remix)”

A tough call because Biggie is only spitting the first verse of the forthcoming “Dreams,” but we decided to allow it because “Dreams” has two additional verses, this is an original song as well as the first time Biggie spits the verse, and it’s a fucking classic.

66. Funkmaster Flex – “Freestyle #13”

There’s a chance Funkmaster Flex’s 60 Minutes of Funk Vol. II is the greatest officially released rap compilation ever produced, including the slew of great rap soundtracks we saw in the late 90s. This track is one of the many reasons why, the musical equivalent of one of those Timbs, North Face and Yankee fitted New York centric memes. The Lox brought something out of Big, the competitive nature of a champion sparked by young challengers, like when an established star squares up with an up and coming young talent the media is comparing to him. We didn’t get enough collabs between the four men, but every time it happened, Big put on a show. 

65. Busta Rhymes – The Ugliest (Or “Modern Day Gangstas”?)

As mentioned before, Biggie and Busta went to high school together at George Westinghouse Career Technical High School in downtown Brooklyn, but you get the impression that in spite of a bit of overlap, they were not the best of friends (By his own account, Busta had no idea Biggie rapped when they were in school together, and Neneh Cherry said as much, recounting a story when the two ran into each other while Big was recording his verse for “Buddy X,” that Biggie said he didn’t fuck with Busta). But the two collaborated fairly regularly throughout Big’s career. This exemplary early Dilla beat was probably their best moment together, a track slated for Busta’s solo debut, The Coming, that was cut because they picked up on the Pac not so sublimals in Big’s verse and Busta didn’t want to get involved: “And the winner is, not that thinner kid/Bandanas, tattoos”. As a result, it took a while for us to hear this in its intended form, finding bullshit second life on posthumous cut and paste jobs.

64. Lil Kim – “Crush On You”

“Crush On You” is one of the more difficult songs to properly rank in Big’s catalogue. Mase was famously paid 30 racks to write five songs for Lil Cease. He broke 5K off for his friend and Children of the Corn group member Cam’ron, who promptly wrote “Crush On You,” an instant classic and major hit at the time. But the details are lacking. Does this mean he wrote Biggie’s hook for him? If he did, does that take away from its perfect and inescapable delivery? Can we imagine the hit landing as hard if Kim, or Cease, or Cam himself delivered it?

It’s a fantastic song for many reasons, one of which is Cease’s great, ghostwritten verses, the Jeff Lorber sample, the remix that Kim improves on, and Biggie’s hook. It would be great if a journalist with more access than we have could go back and do an autopsy of Hardcore and Junior Mafia’s Conspiracy. How much of the content exactly was Biggie responsible for? For now, we’ll leave it here, Cam’s incredible pen plus great performances from Cease, Kim, and Big.

63. DJ Eddie F – “Let’s Get it On”

This appearance really displays the duality of Pac. On “House of Pain” he’s at his listless, cliche spouting worst, but here he’s electric. His wise beyond his years dismay rhymes with Biggie on the rare occasions he deigned to explicitly address social issues. Here, Pac is swinging all over the place, entrenched in pocket. In comparison, Biggie’s verse is fun and frivolous. By my count, this is the one time (1-4 if you include the MSG freestyle) Pac bested his friend and enemy. 

62. Funkmaster Flex – “Wickedest Freestyle”

Another Big loosie that eventually landed in Funkmaster Flex’s lap for one of his studio album “Mixtapes,” this masterful verse was originally recorded for Mister Cee. Biggie turns the moment into an event, having a ball playing a Carson/Hope-ish master of ceremony on the intro over “Ellie’s Love Theme” by Issaac Hayes, before the instrumental (rendered sinister by Big here) for Casual’s “I Didn’t Mean To” drops. A lot of Biggie’s threats and shit talk haven’t aged well. He frequently employed sadism, torture, and even the occult as he would warn off would-be competition. We’ve gone through two revolutions in speech, both in rap and society, since Big passed. 

First there was the hyper-masculinity brought on by Cam and Dipset, basically catching your friends or foes in moments of unintentional innuendo-laden phrasing, and dunking on them for it, and then the enlightenment of being sensitive to sexuality, gender, and sexual trauma, among other words, phrases and lyrics some might find offensive or triggering. You will find none of either consciousnesses in this verse (along with much of Biggie’s raw lyricism), written and performed sometime during the Ready to Die rollout in the early 90s. It’s vile, Biggie at his psychopathic and imaginative worst. There’s a secondary conversation worth having about why Biggie’s language was so extreme and oriented towards shocking and disturbing the listener. The entire approach Christopher Wallace brought to Biggie Smalls was as a mirror held up to society. His intention was to create a character that was fundamentally broken, violent, without compass and willing to do anything to anyone at any time. When you listen to songs like “Everyday Struggle,” or “Things Done Changed,” he’s explaining the conditions that create a Biggie Smalls. 

But on verses like these he was the chilling outcome. As a writer and a genius, was it fun for Big to write for this lost soul who was “crazy and deranged”, constantly dreaming up novel ways to communicate his evilness and alienation? Probably. Was it something he would’ve eventually grown out of? Also probably. Does much of this come across without a macro consideration of his entire body of work when you listen to fun little heaters like “The Wickedest Freestyle”? Probably not.    

61. “Enuff Freestyle (Guaranteed Raw)”

I can’t imagine what it must have been like being in a cafeteria with Big at Bishop Loughlin high school in the late 80s, pounding a beat out on the table for him to rip. Or maybe I can, because that’s exactly what “Guaranteed Raw” feels like. The track contains the battle verse Biggie kicked in front of that bodega on Bedford and Quincy against William Tory “Supreme” McClune, which is why it isn’t included in this list. 

60. Supercat – “Dolly My Baby (Remix)”

An absolute guest stunner from Big. He was Jamaican, and had his dalliances with his roots both here, and on “Respect”, a genre of crossover track that was common amongst Brooklyn MCs in the 90s. The rest of the song is mostly vibes. Supercat kills it, but 3rd Eye and Puff decidedly do not. Biggie’s eight bars are devastating, quickly showing up to drop, “Lyrical lyricist kicking lyrics out my larynx.” an incredible work of alliteration from a guy who didn’t write his verses, and arguably one of his greatest single bars of all time. 

59. “Biggie Got the Hype Shit”

Right up there with “Unbelievable”, or “Machine Gun Funk,” or “Kick in the Door.” Just a ferocious lyrical barrage. This was from a very early recording session with Puff, who I imagine sitting in a cushy leather chair on casters, staring dumbfounded through the studio glass, into the booth like Daniel Plainview at the Little Boston field, watching a geyser spraying oil into the night. The master for this track was lost in a fire that destroyed the Bronx studio where it was recorded, which is why it never saw a proper release, but this rough cut surfaced years ago. 

58. “Miss U”

A heartbreaking dedication to a friend named “O” (Olie, or Roland Young) Big lost in a murder that gained particular relevance in the wake of his own tragedy. I can’t find the quote, but somewhere in my obsessive research leading up to this piece, I found some reporting that alleges we can actually hear O doing hook work on an early Biggie Demo. Biggie was often cavalier about death, both in his hyperbolic and heightened threats, as well as his own vocal acceptance of it in what he had predicted over and over would be a short and violent life. “Miss U” is one of the only times he allowed himself to soberly contend with the pain and grief that comes with loss, and he’s poetic and insightful, allowing a rare window of vulnerability into how much the loss of O hurt him and the people who cared about O. Perhaps this is why it was the instrumental that played as mourners approached Biggie’s open casket after Volleta Wallace read scripture, Puff delivered a eulogy, and Faith sang gospel at Frank E. Campbell Funeral Home, just off Museum Mile on the Upper East Side.

57. “Microphone Murderer”

When people talk about Biggie’s preternatural polish and confidence as an MC, they’re probably referring to this. The whole demo tape is great, but there’s something about this sprawling verse, where he’s both channeling and besting his favorite rapper, Big Daddy Kane, on his own shit. It’s like Biggie’s Game 5 of the 2007 Eastern Conference Finals (I personally lose my mind when he runs through all the Jacksons, a little aside/device that would be sophisticated today). Most of the verse was later rerecorded for the “Another Rough One” freestyle, but this is the one. It’s the voice, the command, the punchlines, it’s all there, already, at the age of 19 in 50 Grand’s basement. You could clean up these vocals and slot the verse in nearly anywhere on Life After Death five years later, and no one would know the difference. 

56. Sadat X – “Come On”

Puff was from Westchester, as were a surprising number of rappers and producers that were integral to the New York scene in the 90s. Puff, Pete Rock, and Heavy D were from Mount Vernon. DMX and the Lox were from Yonkers. Brand Nubian was from New Rochelle. A lot of the early Big loosies can be explained by this Uptown Records/Westchester plug, including this, probably the best of the bunch.

We’ve included the original Lord Finesse version, a decidedly murky and grimier iteration that Puff steamrolled for the version that eventually saw the light of day on Born Again (which is still pretty murky and grimy itself and I don’t hate nearly as much as Sadat claims to). If you’re wondering why the infamous “MSG Freestyle” at the Budweiser Superfest with Scoob Lover and 2pac is not on this list, it’s because Biggie’s verse was featured on this song. This was recorded in 1993, and never saw a proper release because according to Sadat, it was Puff’s punishment for him capitalizing on a clerical error by Bad Boy and cashing two checks for the same session. Whichever version you prefer, it’s an electrifying, vintage performance by both Big and Sadat. 

55. “Nasty Boy”

When you want to attempt to figure out how Biggie may have really felt about 2Pac, you know, deep down, consider he recorded this the night Pac was killed. I can’t imagine a song that dispassionately veers further from trying to grapple with the loss of a former friend whose made himself the bane of your existence than this sex romp.

From Biggie’s perspective, it’s interesting to compare this to the filth he recorded on early tracks like “Bust a Nut” with Luke, the posse cut “All Men Are Dogs”, or even the original “One More Chance”. Biggie was clever and captivating (and, you know, gross) on all of these, but often sophomoric. No one would call “Nasty Boy” a mature statement of purpose, but it’s comparatively evolved. It’s more narrative driven, the scenarios more imagined and colorfully sketched, featuring actual characters that go beyond blank canvases for Big to, uh, project onto (sorry). In other words, while much of his early sexual exploits were communicated in the abstract with punchlines, on “Nasty Boy” he commits to fleshed out Freaky Tales.

54. “You’ll See”

With all due respect to “Last Days,” the consensus choice, this is my favorite of the Lox and Biggie collabs. It was the introduction of the Lox as Bad Boy artists, the B side to Faith Evans’ “You Used to Love Me”, and most importantly, it’s the guys all running wild over the “You’re a Customer” instrumental. It’s a great contrast of style.

The Lox are all squarely in hungry Yonkers kids mixtape mode (A young Styles kicks off ceremonies and delivers the second best performance), but Biggie decides to bring “Big Poppa” energy, going long but staying above the fray with designer drops and beautiful women shit talk. Styles has described Biggie’s come out line, “N***** talkin’ it but ain’t livin it”, as a bit of shade directed towards the Lox, a way of saying, I have all the things you rap about aspirationally. A kind of putting the trio in place. “You’ll See” feels very much like a war room session with the wizened head of a family and his three overzealous shooters looking to make names for themselves, that he’s keeping on a leash.  

53. “Friend of Mine”

In all things, Biggie projected confidence. There are few flows in the history of hip hop that were even on the same planet of assurance he was operating in, whether warbling off key on a piano bar ballad like “Player Haters” or going toe to toe with Jay-Z or Meth, so it would be easy to think of him as invulnerable. But Biggie was overweight, had a lazy eye, and working class most of his life. He talks about it occasionally, calling himself fat and ugly, telling stories about beating up kids who teased him for wearing bootleg Lacoste and Le Tigre gear, making offhand jokes about his wife cheating on him with 2Pac on “Brooklyn’s Finest.” It’s hard to know how he really felt about these things, but to me, it always had the flavor of classic Jewish self-deprecation, calling himself out before others could. We see some psychology on “Friend of Mine,” a parable about a woman who fucks Biggie’s better-looking friend (presumably Damien “D-Roc” Butler), resulting in him smutting her out.

The rough edges of the song are smoothed, we don’t get much in the way of vulnerability or hurt feelings, perhaps betrayal both by his girl and his friend, but you need to read inflection and subtext. It’s sadly in the glee he takes in his revenge as his career takes off and he’s empowered, returning his hurt, in the warble in his voice as he appraises his man D’s game, it’s in Easy Mo Bee’s hook, sampling Black Mamba’s “Vicious”: “You know that ain’t right, when they’re friends of mine”,  it’s in his need to make the song at all, showing and telling us why he’s “earned” the right to be callous and cruel to women he hooks up with. It’s sneakily one of the clearest pictures we get of Biggie’s insecurities.

52. “Road to Riches” (Or “Real N*****,” or “West Coast Freestyle”)

This track was allegedly released as an album promo and finds Big rapping over “Deep Cover”, “Nothin But a G Thang”, “Black Superman,” “Murder was the Case,” and “Gin and Juice.” But really it’s a short story collection loosely held together by a great, Kool G Rap quoting hook. The first two verses are vaguely Goinesian, perhaps a touch of Puzo, but the third, featured on what ended up probably being Biggie’s best known posthumous hit “Notorious”, feels more like an indulgent horny comedy, Phillip Roth or Sam Lipsyte. Whatever your preference, because it has only been served up “properly” in bits and pieces, it doesn’t get credit for being one of Biggie’s best series of narratives, but it is.

51. Shaquille O’Neal – “You Can’t Stop the Reign”

Something Biggie fans like me wrestle with constantly is the crucial and incredibly consequential question: “Which Biggie is your favorite?” He had so many styles and personalities that he could float between. The purists will tell you it’s the ass whipping wunderkind of “Unbelievable”, perhaps the double timed stylist of “Notorious Thugs,” the grimy hater on “Gimme the Loot”, the shockingly tender and human poet of “Miss U” and “Juicy.” And then there was this persona, sort of birthed with songs like the Stay With Me remix of “One More Chance” and “Big Poppa,” but really a style that found its final form on Life After Death, and gorgeous tracks from that era like this collaboration with Shaq, a friend of Big’s he was on his way to see the night he was murdered in Los Angeles. 

This song was the maturation of a project Puff spent the entire first half of his career developing: The integration of R&B and hip hop. While it started with R&B artists singing over rap records, it eventually mutated into a hybrid of rapper spitting over softer, R&B infused production. The period around Life After Death saw some very good iterations of this, off the top of my head, specifically much of LL Cool J’s Mr. Smith, and Heavy D’s Waterbed Hev. But of course Biggie was the best at it, and perhaps never better in this lane than he was here (Rick Ross for instance, can thank just this song for the whole second half of his career, when not in Luger Trap mode).

There’s just an intoxicating luxury to this song, it’s SO fucking smooth, both in his dulcet tone and the way the verses flow on a bed of cold pressed, unfiltered olive oil (The Chris Large smooth jazz, drawn butter drenched production gets an assist as well). Biggie isn’t just dropping name brands and bragging about his wealth and access, he found a way to make something that SOUNDS rich, it FEELS rich, like a brand new pair of lined Timbs or the weight and smell of a fresh leather. It’s a lobe of foie gras, a spoonful of caviar, a truffle supplement. Rappers still try to capture moments like this, to make opulence flesh like this does, but none can match it. For his many innovations, this textile approach to rap and bullshit may have been Biggie’s most influential and impactful, and yes, sometimes it’s my favorite.  — Abe Beame

50. “Last Day”

“I did real songs with Big, no made up shits” is a perfect diss record bar in the sense that there’s no real rebuttal available. In fairness to 50, he was still learning the ropes from Jam Master Jay when this song was recorded, but rap battles aren’t about fairness. And when you have a card that good, you have to play it. This Life After Death cut is the crown jewel of said real songs, a posse cut that still makes me marvel in the present.

Every LOX member brings their A game to the festivities, as to be expected. The jarring part is when the man himself drops by at the end. A very good song takes a flying leap into greatness, as Big’s enemies are unable to sleep, too haunted by nightmares of his dominance. He jumps from two interwoven crime scenes that both beg for their own song length elaborations into the verse’s undeniable highlight: “make you a classic like my first LP”.

There’s something to be said for not waiting for anyone else to give you your flowers. Big wasn’t about to wait for someone to tell him what he already knew. Ready to Die was going down in the history books. The “Last Day” verse is a masterclass from an artist in full command of his craft. The LOX went on to make their own mark, but on this one, they were simply Jimmy Jump to Big’s Frank White. — Jeff Castilla

49. “Been Around the World”

There’s simply too much going on in Diddy’s “Been Around the World” to not revisit the craziness. For the Bad Boy founder’s debut studio album No Way Out, Diddy channeled David Bowie’s “Let’s Dance” for its third track and tapped Mase and Biggie to hold down feature duties. The music video singlehandedly recreated the opening to Face/Off, tapped Vivica A. Fox as a suburban house mom, featured Diddy on the toilet talking to Quincy Jones, found Wyclef Jean tapping phone calls and attempting to crash Diddy’s private jet and ended with some salsa dancing with Jennifer Lopez [Ed. Note: Patrick is somehow underselling this, do yourself a favor and watch if it’s been a while. It’s fucking insane Puffy at his most Bay/Fincher level preposterous].

It all somehow managed to work together beautifully. Biggie did the most with his brief albeit memorable posthumous feature, released just eight months after he passed, channeling Lisa Stansfield’s “All Around the World” for a half-sung, half-rapped chorus. As Bad Boy shifted into the label’s next phase, one that would rely heavily on Mase after B.I.G. ‘s death, “Been Around The World” found Biggie prepping No Way Out listeners for one last hurrah. His memorable features on “Young G’s,” “Victory” and “All About the Benjamins” were more substantial, but none were as experimental and greater than the sum of their parts as “Been Around the World.” Plus you left with The Madd Rapper and Madd Producer hating on Biggie’s “Hypnotize” video and incredulously remarking on the video having mermaids. — Patrick Johnson

48. “B.I.G. Interlude”

Some time between recording his famous demo tape and finishing Ready to Die, Christopher Wallace switched his official stage name from Biggie Smalls to The Notorious B.I.G., which he would stick with for the remainder of his life. But he never stopped accumulating nicknames. One of his favorites was “Frank White,” as in “the Black Frank White,” as in the Christopher Walken character from King of New York who was modeled in part on the Philadelphia rapper Schoolly D, a friend of director Abel Ferrara. Schoolly D, of course, had become famous back in ‘85 for “P.S.K. What Does It Mean?,” which was more or less gangsta rap’s Big Bang. (In today’s era of cops and prosecutors using rappers’ lyrics to incriminate them, “P.S.K.”’s coyness about gang initials holds up tauntingly well.)

The “B.I.G.” interlude, which flips the “P.S.K.” hook and treats Big’s vocals with the same mid-Reagan echo, is tucked between “What’s Beef?”––where Big chuckles that he’ll let his trembling enemies keep their jewelry, but Puff is stone-faced––and “Mo Money Mo Problems”––where Puff and Mase are relaxing on yachts while Big sneers at the DEA. Life After Death is a masterpiece, perhaps the only masterpiece, about the experience of being a rap star, and its dozens of disparate parts are held together by Big’s mastery of tone: sly when you think he’s being obvious, winking when you think it’s a threat. What better way to underscore this than to spell his name while alluding to a record famous for obscuring its true topic? “What?” he cracks at the song’s end. “It ain’t no more to it.” — Paul Thompson

47. Total – “Can’t You See”

There are few greater demands than asking for all the women within an 8,122 mile stretch, but the Notorious B.I.G. was not one for small orders. On Total’s ’95 “Can’t You See,” B.I.G. teamed up with the R&B trio and sent out a PSA to “all the chickenheads from Pasadena to Medina.” 

While Total narrowed in on their one and only sweetheart, B.I.G. claimed a flock and then some, kicking off the sultry love song with a touch of sex, death, and a nod to his clique. Total, of course, eased right in with their first verse, and the Sean “Puffy” Combs-produced, James Brown-sampled track rolls right on. B.I.G. did his part, and now the girls got the last word.

This hip-hop and R&B alliance was less “men are from Mars, women are from Venus” and more of an example of how the two genres, genders, and expressions balance each other out. And no one knew this better than B.I.G. It was, after all, Total who sang the hook on “Juicy” and the group’s Pamela Long who swooned over Biggie Biggie Biggie’s words on “Hypnotize.” 

This time, B.I.G. did the ladies a favor, lending his star power to the single on the Bad Boy trio’s debut self-titled LP. “Can’t You See” would peak on the Billboard Hot 100 at #13 and the Hot R&B/Hip Hop Songs chart at #3, and the Bad Boys and Bad Girls would see another ’95 win.  

On “Can’t You See,” B.I.G. set the tone and dropped the mic. And in the end, what B.I.G. brought was balance: the confidence to know the song didn’t always need to be his and the cool to know that he’d always be what made the song. —Paley Martin

46. “The World Is Filled”

Biggie’s pimp rap song is the best posse cut he was ever part of. Yeah, I know “Flava In Ya Ear” Remix has That Verse, “Notorious Thugs” is mind-bending, “Mo Money Mo Problems” is perfect, but they all share something in common: Biggie steals the show. It’s like watching LeBron in his second Cavs stint — a lot of fun, a few nice complementary players, but you’re not really checking for Kevin Love.

“The World Is Filled” is, by my estimation, the only group song where Biggie doesn’t outshine the other rappers. That’s not a slight against him — his verse here is classic — but you have a surprisingly charged-up Puffy doing his absolute best Ma$e imitation, saying misogynistic things in the slickest way, and then there’s Too Short, taking to heart Carl Thomas’ delirious chorus about pimps and hoes and doing the verse he was born to do. He was 10 albums deep when they made this; he had his rap style down to a science. 

It’s just an absurdly brilliant record. All the parts lock into place. Maybe it was the atmosphere in that session, as Too Short described it: women lounging around Puffy’s studio, weed smoke and booze smells clouding the air, everyone being noisy as hell, Puffy giddily showing everyone how good his verse was. It seemed like a fantasy; maybe it was just a hotbox. Whatever it was, Biggie emerged out of it with a verse committed to memory. The Remy was in the system. One take and he was finished. — Mano Sundaresan

45. “Queen Bitch (Guide Vocals)”

I had a debate on Twitter recently with a cabal of studied hip-hop nerds I both like and respect who took a shot at Biggie for his use of language. They went after a throw away line on Life After Death’s “What’s Beef?” in which Biggie claims his associate Gutter kidnaps kids, rapes them, and throws them off of bridges. I tried to make the case that literal readings of Biggie verses like this were reductive, an insult to his project and a misreading of his intention, which was interpreted in this instance as somehow bolstering his bona fides as a thug with wildly absurd and over the top menace like this.

Well folks, if you want to see how literally to take Biggie when he’s talking his shit, I couldn’t come up with a better counter than him referring to himself as a “bitch with that platinum grammar.” Maybe second only to Biggie Smalls himself, Lil Kim was Big’s greatest creation. She was a bottom chick who would shoot, fight, and fuck like a man (echoes of raw female blues protagonists like Bessie Smith), and would change the unapologetic, flaunted sexuality and proud gangsterism of female MCs forever. In Kim, with songs he clearly wrote and even performed guide vocals for like “Queen Bitch  (a lyrical workout that stands shoulder to shoulder with his very best showcases), Christopher Wallace shows his talent as a writer and thinker, equally able to embody Biggie Smalls as he is that character’s gangster moll. He proves that if we’re to take his flights of fancy at their word, we’re diminishing his imagination and ability, and the joke is on us. — Abe Beame

44. “One More Chance”

Ready to Die is a snapshot of a creator and art form evolving by the hour. You can hear it in beats ranging from Easy Mo Bee’s late Golden Age funk to Preemo’s state-of-the-art boom-bap to Chucky Thompson’s R&B-inflected grooves presaging Bad Boy’s pop tendencies. You can hear it in Biggie’s youthful flow – higher-pitched and busy compared to the more  poised, measured baritone delivery that would become his signature. And you can hear him trying on personas – whether it’s the neighbourhood dude turned local hero, the psychotic stick-up kid, the ice-cold criminal mastermind and perhaps most notably, the lady-killer.

In ’93, when the first album cuts were being laid down, sex rap was basically locker room talk. First-rate contemporaries Heavy D and Big Daddy Kane would fatally wound their own careers by making slow jams that prioritised seduction over fucking. But for Big, this was just another old-school shibboleth that he’d crush through the sheer force of his talent and charisma. 

In a 1998 profile in Spin, writer Sia Michel describes Wallace as “a shy, warm-hearted, deadpan funny, dick-waving lost boy who made you want to hug him one minute and slap him silly the next.” Those qualities are everywhere apparent on “One More Chance.” If the smash remix saw Biggie play the irresistible silver-tongued mack over a club friendly groove, here he’s the priapic teenage pussy-hound, neck-deep in the perks that come with being a successful rapper, over a porno beat.

An answering machine message of his infant daughter telling “the hoes to stay off his dick” pretty much sets the tone. He’s totally jazzed on being a fat ugly sex magnet and if nothing else, he sets expectations up front. He’s obnoxious and lewd but witty enough to get away with it. The sexual politics are questionable but he’s the first male rapper I ever heard talk about giving head, although as the song’s most hilarious lines warn, you better know how to comport yourself when Big Poppa “goes down below.” If sex is in the mind, then lyrical intelligence is the ultimate aphrodisiac. — Joel Biswas

43. “Just Playin (Dreams)”

“Just Playing (Dreams)” is a concept track wherein Biggie namedrops every hot female R&B singer of the 90s before sharing whether he’d hit it or not, how, and why. Think about that for a second: this shit just wouldn’t fly in an era of instant reactions. Sure, Nicki Minaj can reclaim the concept (or bite Lil Kim’s version) under the cover of feminism, but she pulled more punches than a celebrity prize fight. Meanwhile, the original sees Biggie setting things off with a reference to Patti Labelle’s sexual assault, saying he’d give Tina Turner Ike flashbacks, and claiming he’d fuck RuPaul over Xscape. Good luck getting away with that post-Twitter, because to quote a completely different song: things done changed.

And yet “Just Playing (Dreams)” worked for reasons beyond the 90s being a bastion of shock-jock humor. For one, there’s obvious affection in Biggie’s voice, and underneath his authoritative baritone, you can almost hear this 21-year-old kid chuckling to himself under his breath. While Mariah Carey almost certainly didn’t appreciate being called scary, it hits different when the guy saying it called himself Black and ugly as ever, on his own hit single. The song may be childish, but it wasn’t intentionally cruel.

The other reason “Just Playing” works is because deep down, it’s a pretty nerdy song. Don’t forget, you couldn’t just Google a list of R&B singers in 1993, so the song was a hint that under Biggie’s tough guy exterior and King of New York image, he was drooling over the day’s superstar divas just like the rest of us, and paying attention to celebrity news while doing so. At the end of the day, that he got away with it  shows just how much affection and good will there was for Biggie at the height of his powers, even when he was being kind of a dick. — Son Raw

42. Lil Kim – “Drugs”

Christopher Wallace was clearly larger than life. But if there’s one aspect that’s fallen through the cracks more than any other these last 20 years, it was his role as head coach. If you locked down studio time with him, he’d be sure to coax greatness out of his peers. And if he penned you a verse, you were guaranteed a classic track. 

Lil Kim’s Hard Core was certified double platinum, sold 5 million copies, and cemented her path to becoming a Top 5 female MC. Female rappers like Lyte, Latifah, Rage and even Shante had already laid the foundation, but the Brooklyn Queen Bee kicked down the door. 

Hardcore by name, Hardcore by nature, Lil Kim came with a sexual carnality that no one had ever seen before. She single-handedly raised the bar for raunchy lyrics in hip-hop by rapping rhymes like “You ain’t lickin’ this, you ain’t stickin’ this . . . I don’t want dick tonight/Eat my pussy right.”

Her blend of provocative sass had become a narcotic. Her bracing confidence made most male rappers quiver. 

Kimberly Jones freestyled for B.I.G on a street corner and transfixed him on and off wax. Shortly thereafter, he recruited her to join Junior M.A.F.I.A.  

On a contact high Biggie and Kim struck up a tumultuous love affair. He became her mentor, got to work as executive producer of Hardcore, and slid on a quartet of tracks himself. One of those being “Drugs.”

A wavy B.I.G. croons the hook, comparing Lil Kim’s potency to Sensimilla(a female marijuana plant) among other stimulants and confesses that touching her, and being immersed in her vibe is the ultimate rush. While Kim taunts, teases and pistol whips listeners rapping about jewels, fur, cash, liquor, sex and invitations to “lick her ass” coded in Arabic slang. 

Backed by the warped, lysergic Shaft sample, Kim flexes her lyrical prowess and gives up the goods with slick cadence and tongue twists that pay homage to B.I.G and lingers long after the high wears off. — Tracy Kawalik

41. Junior M.A.F.I.A. – “Player’s Anthem”

Biggie’s gift was that he was equally gifted at rapping at stealing your girl as he was spitting about robbing dudes in Clinton Hill. On ‘’Player’s Anthem’’, he says ‘’rub your tities if you love hip-hop’’ but true to form, he is also boasting about how he’s been robbing dudes since he was Run DMC. Like ‘’Juicy’’, ‘’Player’s Anthem’’ is also a celebration of making it from selling crack in the hood to having caviar for breakfast and champagne bubble baths at night.

Lil’ Kim is in rare form here; the best part about BIG and Kim’s music together is you can feel the attraction that they had for one another in real life. BIG says that if robbery was a class, he’d pass it. Kim reminisces about being Keisha in New Jack City, packing MAC’s in her cadillac before Pun. At the same time, Kim never fails to remind us that she is the boss. She is teaching the game to all the D-Boys that think they have it.

To see BIG and Kim is to see two forces coming together with their own unique sexual energy. BIG, a heavy Dolomite meeting Richard Pryor; Kim, a “running the block with her man” version of Pam Grier. As a dark skinned Black woman, Kim was given a raw deal by society that has racist and sexist beauty standards. In a world that values lighter women, she was made fun of until her skin became light like those women she was pinned against. She wasn’t allowed to embrace herself like BIG was (Some of that is because of BIG himself; he wasn’t perfect). That’s unfortunate, because they were perfect together; there wasn’t a male and female rap duo that was better. — Jayson Buford

40. “One More Chance (Stay With Me) (Remix)”

The feel good music video for 1995’s “One More Chance” remix shows Biggie chillin’ on the stairs at a dimly-lit house party, which is tellingly chaired by rap’s original 320 lb. sex symbol, Heavy D. He’s talking his shit while receiving kisses on the cheek from a whole host of female admirers; it remains a beautiful time capsule. 

It captures 1990s rap culture just before all the crippling paranoia set in (something Big arguably got lost in himself with Life After Death), with an infinitely cool Biggie rocking his navy blue Kangol like it’s a crown. But aside from capturing Biggie at his most carefree, the “One More Chance (Remix)” remains important to the late rap legend’s legacy because of the way it cemented his unlikely sex appeal, something that often gets downplayed when we talk about what made Brooklyn’s finest emcee so unique. 

The original “One More Chance” was basically a horny horrorcore track, with brutal lyrics about shattering bladders and shifting kidneys not exactly ageing well. However, the remix traded those filthy bars for butter smooth boasts from Biggie about his “immaculate” bedroom skills. He wisely replaces the “I got that good dick” taunt for “I got that good love” on a soothing hook, which also contains seductive coos from Bad Boy’s own Charlie’s Angels, Faith Evans and Mary J. Blige. 

This remix, which peaked at no. 2 on the Billboard 100, proved the Frank White and Big Poppa personas were two sides of the same coin, with Biggie effortlessly able to shift gears and make music that all sexes could dance along to (just like Tupac claimed he had advised Biggie to do). I don’t want to give the impression Biggie was the father of the body positivity movement, but he definitely wrote a blueprint for artists like Big Pun, Rick Ross and Fat Joe to follow, effectively creating a lane for overweight male rappers to convincingly channel their larger-than-life confidence into becoming improbable Lothario’s.

On this dance floor-filler, Biggie has a woman on each arm and a blunt in each hand, reigniting the magnetic lure of Barry White in his Can’t Get Enough heyday. Rapping against a laid back flip of DeBarge’s soppy-eyed “Stay With Me”, Big’s velvety flow is an ode to the art of fornication. He makes it clear that his size and appearance (“Heart throb never, Black and ugly as ever”) won’t get in the way of slick-talking your girlfriend into bed, and I can’t picture a day where this unshakeable self-assurance won’t feel contagious. — Thomas Hobbs 

39. Mary J. Blige – “Real Love (Remix)”

Biggie’s appearance on Mary J. Blige’s “Real Love (Remix)” is another example of doing the most with less. It’s an efficiency masterclass. He spends just 20 seconds and under 12 bars on the remix to Blige’s first top-ten Billboard hit, coming in at the 2:20 mark and announcing, “What up? My time is up…” at 2:40. While the intro caught most of the attention with its sample of Betty Wright’s “Clean Up Woman”, Biggie spent the entirety of his verse over the drums of EPMD’s “So Whatcha Sayin’” courtesy of producer, fellow Brooklynite and childhood friend Daddy-O. “Look up in the sky, it’s a bird, it’s a plane/ Nope it’s Mary Jane, ain’t a damn thing changed,” is a picture perfect opening bar. This verse, like so many of Biggie’s features, leaves you wanting more. — Patrick Johnson

38. “My Downfall”

In 1997, rap kayfabe was at an all-time high. The intersection shooting where Biggie Smalls’ life was ended by shots fired into a Suburban door was the downturn of rappers keeping it “real” at all costs. Most of the time nowadays, we’re privy to rappers playing characters, rappers not really doing the things they say they do. After the murder of Tupac Shakur just six months prior, the likelihood of Big’s life reaching a violent, tragic end was somewhere south of the neighborhood of farfetched. I’ve read the word “prescient” a lot when reading about the violent paranoia of the final three songs on Life After Death. But it wasn’t exactly like Biggie predicting his own violent death was a miracle leap of psychic intuition.

In the final trilogy of songs on Life After Death, particularly “My Downfall,” Big shows his gifts of his imagination by melding the dark clouds of real life with lavish fantasy and deepening the Legend of Biggie Smalls as the most impressive folklore in this genre called rap. Only Biggie has such depth of range to conjure the image of his own funeral, brag about his forays into amateur porn, and add the origin of his lazy eye to his carefully and fastidiously crafted self-mythology. Only Biggie has the sense of humor to mistake heavy breathing on the other end of a threatening phone call for his wife.

A potent mix of Jamaican rum, whiskey, and a heavy pour of fatalism, “My Downfall” finds the Bed Stuy legend ruminating on the quiet of dying and the weight gain which comes with it. Over its music accompaniment — the midpoint between dramatic and mournful — he basks in the opulence to troll the broke cats covetous of his riches. Puffy is given the intro and the outro to passionately rebuke jealousy and those who find themselves in the throes of it when they see Big and Puff shining. Darryl McDaniels stands in the midst of the tension to acknowledge the praying hands fixated on the downfall of an immensely talented artist. 

Biggie’s role in all this is to stand in the midst of the avarice and forces marching to execute his downfall with dignified and cavalier testaments to loving his life. After all, ain’t no shook hands in Brookland. — Douglas Martin

37. Puff Daddy – “Young G’s”

“Young G’s” is a snapshot of what the Commission could’ve been.

I’m obviously obsessed with the Firm – I write about them on this here site every 8 months.

The biggest difference between The Commission and The Firm is that Biggie would’ve controlled the careers of Cam’ron and Charli Baltimore and partnered with Jay and Rocafella.

The Firm was an uneasy political balancing act — the labels were not allowing Nas, AZ, and Foxy Brown to be on every song to make Dr. Dre and Steve Stoute rich. That’s why The Firm album had Nature, Noreaga, Half-a-Mill, and Canibus filling in the gaps – they were utility players playing multiple positions. The superstars of The Firm were literally limited to 3-5 songs each.

The Commission would’ve been the MCU of east coast rap. We already had “I Love the Dough”. We had Biggie shouting out The Commission on “What’s Beef?”. “Brooklyn’s Finest” might be the best song on “Reasonable Doubt.” Cam and Charli went to UnDeas Entertainment, originally a venture between Big and Lance “Un” Rivera. Rocafella ended up doing a quarter-water deal with Def Jam for Jay’s solos and could have partnered with Bad Boy for an even bigger payday.

Biggie was quietly becoming a genius of marketing following in the footsteps of Puff – Junior MAFIA existed as the Boyz II Men to Biggie’s Michael Bivins. He and Jay both were getting ghostwriting cash for Lil Kim, Foxy Brown, and Bugs Bunny on the Space Jam soundtrack.

I say all of that to say “Young G’s” was deliberate. Another Big and Jay collabo, this time on Puffy’s album, originally set to be titled “Hell Up in Harlem” before Big’s passing. Phase I was complete.

Produced by Tumblin’ Dice and flipping Oliver Sain’s Beatles cover of “On the Hill,” most familiar to rap fans for the D.I.T.C. banger “Day One.” “Young G’s” is another tour de force between Jay and Big with a ghostwritten verse for Puffy by Sauce Money.

When the song finally hit on No Way Out, it was a mixtape and album cut favorite. Any Biggie rhyme was required listening, and his verses on “Victory’ to set off the album might be his two best verses ever. And here was Jay, barely certified gold thanks to Foxy and the Nutty Professor soundtrack, hanging with the best rapper in the world, talking that elevated self-actualized kingpin shit:

“I been rich, I been poor, I saved and blown bread
Some say I been here before because of the way I zone
Some said, Jigga zone’s like the falling of Rome
Reoccurring, that he thinks like that ’cause he’s observant:
Won’t be known until I’m gone and n*gg*s study my bones
Mentally been many places, but I’m Brooklyn’s own”

Jay did 28 bars, a very atypical structure for a major label rap feature in any era.

And then Big laid down his 24 bar verse, parotting Jay’s talk about women taping drugs to their thighs to make those rounds out of the country.

“While I just, slang coke, smoke pounds of choke (uh-huh)
Got lawyers watching lawyers so I won’t go broke, now check it
Them country n*gg*s call me Frank White
I’m squirtin’ often in my loft, of course I know my shit’s tight
Sunrise, open my eyes, no surprise
Got my shorty flyin’ in with keys taped to her thighs”

When you are 24 with only five years of major label experience to your name, and you talk about hiring lawyers solely to keep other lawyers from extorting you, you are destined to be a success long term.

The song is called “Young G’s” but this was graduate school. “I Love the Dough” and “Brooklyn’s Finest” were gleaming celebrations of the Big Willie Era, surviving the crack game, and making more money than almost any rappers before them. “Young G’s” is all of the days in between the popping of bottles, the ground level wild shit you digest, the education you get that comes with a severe cost. It’s the most somber of the Jay and Big collabos, even on an album from the Shiny Suit Man who deliberately mapped out a 2 year run of radio dominance during the making of the album.

Puffy told his Hitmen in 1996 “For the next two years, I wanna have radio on lock. Call the girlfriend, wifey, or whatever, and let ’em know that you’re not gonna be around for a few weeks. We’re gonna get away from all this drama, put our heads together, and when we come back, we’re coming back with hits.”

“Young G’s” was never a hit, but it’s the most honest look at Jay and Big, young men with real plans for ownership, who made it through hell and could rap about it better than anyone without using a pad or pen. —Zilla Rocca

36. “Respect”

The Notorious B.I.G.’s was the captivating narrator and a joyous master of street corner ceremonies. His macabre streak included a penchant for toting pistols and hustling until sunrise; he was gregarious and gangster, extrovert and introvert. He was prolific because he understood duality’s relation to art. No one saw this more than Puff. 

Poke (of the Trackmasters) and Puff perfectly laced “Respect.”  The beat cleverly loops a section of “I Get Lifted” by KC & The Sunshine Band, shifting the pitch down several semitones. Included on his debut album, Ready To Die, this song is special because it really brings out B.I.G.’s Jamaican roots, with Diane King’s patois up front and center. 

Against a world that seemed to give up on him before he was able to grow facial hair, “Respect” recounts the origin story of a street maverick who plays the hand he was dealt to settle the score. Voletta Wallace raised her single son without the help of his father, and B.I.G. was inherently tied to his mother’s presence. On “Respect,” he lays out grim details of her late pregnancy: “10 months in this gut/what the fuck?” Lines like this reveal the urgent necessity of survival that he felt even as an adolescent. 

Yet on “Respect,” B.I.G. ‘s excitement is most palpable when he sees his mother smiling, not at the promise of blunts and blondes. He notes her reaction as a welcome surprise. By the third verse, it’s B.I.G. paying his respect to the macs, the gunmen, and everyone else who influenced his music in the early days. He doles out praise and spreads love to the litany of characters on Fulton Avenue, while stressing the need for kevlar. Part corner kid, part Momma’s boy, B.I.G. channeled the world’s duality through his music with effortless charisma. — Evan Gabriel

35. Puff Daddy – “All About the Benjamins”

On its face, I kind of get why DJs feel the need to switch up just before the Biggie verse drops whenever they play “Benjamins” in bars or clubs. The beat abruptly switches from a great Barry White flip to a great Jackson Five flip, and Biggie’s presence is a tonal shift. The song quickly mutates from a fun late 90s Bad Boy all star posse cut/bitch sesh to the voice of God booming over the plains, relating biblical scripture about women sneaking drugs through TSA in their delicates, readymade for chiseling onto a stone tablet. But really, there’s no excuse. Not in Brooklyn, where Biggie is from and his visage is sacred, not in countries where they don’t speak English and have never heard of him (if such a place actually exists). It’s a crime against art, a crime against great writing and a crime against great performance. For the love of Big, DJs: Let the song finish. — Abe Beame

34. “Me & My Bitch”

Big wrote any number of songs, verses, asides, etc. that could function as their own narrative universe. “Me and My Bitch” is particularly incredible because of the tonal shifts that take place throughout the song. It kicks off with a paraphrased Richard Pryor bit (please stop bringing up that line every time you want to discredit Big, it just makes you look stupid) and quickly becomes a coming of age romance. 

There’s a bit too much “why I oughta!” + “to the moon, Alice!” on this one not to be noticeable in the present day, but there’s a certain Ralph Kramden, tongue in cheek vibe to the proceedings that makes the whole thing a bit more palatable. After all, his paramour also gets her chance to politely invite him to a fistfight one verse later. It’s easy to hear a laugh track as you envision Biggie’s Polos and Timberlands flapping in the breeze.

By the third verse, things are far more somber. The tragic ending doesn’t need to be rehashed here but the songwriting template would eventually be borrowed by other New York rappers to great effect, i.e. Lost Boyz’s ”Renee.” Only Big could jump from romantic comedy to coming of age tale to a third act this emotionally affecting without missing a beat. — Harold Bingo

33. 112 – “Only You (Remix)”

I met Sean ‘’Puff Daddy’’ Combs once. See, Puffy went to Mount St. Michael Academy in the Wakefield area of the Bronx. It is located at the last stop on the 2 Train line on the border between the Bronx and Mount Vernon. A Marist Brothers catholic school where they call detention ‘’JUG,’’ short for ‘’Judgement under God.’’ It’s predominantly Black and Latinx kids from the Bronx or Westchester. You aren’t allowed to have braids, facial hair, or have any article of clothing that they deem inappropriate. What is funny is that  I, too, went to this school. Puffy refuses to give back money to the school; the reasons are of urban legend in that area of The Bronx. One reason is because the Head Football Coach, Mario Valentini, or Coach V as we called him, cut him his senior year. Another tale I heard is because he couldn’t afford it.

For whatever the reason, Puffy hasn’t been back and refuses to give back to a school that needs the infrastructure, technology, and the resources that Puffy could bring. When I met him, he had agreed to let some kids from the school come to his Howard University commencement speech. This was the first contact the school had with him since fame hit. He told me, one of five kids there, that he wasn’t cutting us any check until ‘’Valentino’’ hollers at him about the fact that he was cut from the Football team. It’s a ‘’suck my dick, I’m Puff’’ moment that I will never forget seeing right in front of my face.

Bad Boy Records at its peak combined three musical sub-genres: Mafioso rap, Shiny Suit Rap, and New Jack Swing R&B. The A&R skills of Puffy were excellent; he was a master of taking raw talent and putting it over radio friendly production that played to the artists’ strengths. ‘’Juicy’’ is an obvious radio smash, but because of BIG’s deep voice and Jamaican Patios over such a notorious sample, it works like gangbusters. Puffy was also adept at bringing his talent together for huge moments that played like the equivalent of New Years in Times Square. 

Big never sounded out of place on a song with a Bad Boy artist. The music videos were full of colors, weird dances, and suits so shiny they would blind you. Whether it was Faith Evans, Mary J. Blige, Total, or 112, Big sounded in tune on the song. ‘’Only You’’ is peak Bad Boy: A beat that you can get down to at the club like it is the electric slide, plus tight verses that would make the whole block gather around and rap it. 112 was Boyz II Men in matching NASCAR jackets, Chucky Thompson’s production meets Babyface-like songwriting. If they were finessing, then BIG was the brutalizer, bulldozing everyone while still spitting game as good as the R&B dudes were. Who cares if Puffy doesn’t want to give money back to my high school? ‘’Only You’’ taught me more than any textbook could. — Jayson Buford

32. “Somebody’s Gotta Die”

Two and a half years: that’s how long listeners had to wait for a new Notorious B.I.G album. Sure, Biggie had been productive in the interim, dominant even, but the first proper song on Life After Death had the unenviable task of setting the stage for a sprawling double CD epic while also making it immediately clear that the king was back. “Somebody’s Gotta Die” accomplishes this by introducing us to Biggie as the rap Alfred Hitchcock, a new vantage point from which to deliver the vivid storytelling and anti-hero persona he’d developed on Ready To Die. While that album’s narratives benefited from immediacy, throwing us into the middle of the action, ‘Somebody’s Gotta Die’, like “N***** Bleed” and “Story to Tell,” are less suggestive of an actor mid-performance than a director carefully crafting a scene. 

Over stately Carlos Broady and Nashiem Myrick production that wraps a sly Dramatics chop in synth strings and sound effects, we rejoin The Black Frank White in deep contemplation, just as he’s interrupted by an unexpected and blood-soaked visitor. The stage is set with precision, the delivery careful and methodical, the confidence supreme, and what follows is tale of revenge and murder gone wrong. More importantly, the listener is introduced to a version of Biggie that seamlessly blends fact with fiction. Was Christopher Wallace really some sort of rap antihero recording platinum hits by day while delivering street vengeance by night, right under Puff’s nose? Absolutely not.

Yet “Somebody’s Gotta Die” gets to have it both ways: the setting and characters are detailed enough to create a suspension of disbelief, but the relaxed delivery and kayfabe breaking references to Snoop and Puff emphasize that Biggie is fully aware that this is a genre piece: he’s creating a masterful story rap for our entertainment, not reporting reality. This tension between fact and fiction is at the heart of Life After Death’s best tracks, even as the bloodshed Biggie wrote about was already spilling into reality. It’s to his credit that he pulls off this tightrope act so effortlessly, even as his peers were routinely mocked for their own mafioso fantasies. — Son Raw

31. Puff Daddy – “Victory”

From the release of Ready to Die to the night of his murder, the public career of Christopher Wallace lasted less than two and a half years – a halcyon reign briefer than Otis Redding or Hendrix.

He powered Bad Boy Records to the pinnacle of pop music, a generational talent sprinkling fairy dust over an assembly line of hitmakers – Craig Mack, Faith Evans, Total, 112, Mase, Mario Winans, the Lox – not to mention affiliates like Lil’ Kim, Junior Mafia, Charli Baltimore, and Cam’ron. Whether you wanted to make love to your lady or ride on your enemies, Bad Boy had the soundtrack. It was all knitted together by the black Frank White, who could make any song hot with an adlib, presided over by the hottest music impresario in America.

Puffy’s solo debut, No Way Out was supposed to be both a victory lap and a label showcase, but by the time it dropped, its opening song, “Victory” was more like a last stand. D-Dot and Amen Ra’s production sounded like something that should be playing on the USS Nimitz when scrambling a fleet of F-15’s while Puffy’s opening lines (“Yo, the sun don’t shine forever/ but as long as it’s here then we might as well shine together”) could have improved Patton’s speech to the Third Army. Over the course of two flawless verses, Biggie distils his flow to its essence without wasting a syllable, leaving us to marvel at the fearsome brilliance of his ice-cold mafioso shit-talking and reckon with what we had just lost.

Lines like “Rhyme a few bars so I can buy a few cars/ and I kick a few flows so I can pimp a few hoes” aren’t just statements of fact; in his inimitable voice and flow they are the physical embodiment of this truth – a monument to greatness before which all resistance is futile. He appeared to be setting up for his next project, the presumptive supergroup the Commission which would have been what the Firm should have been. His second verse, recorded March 8th, was his last. — Joel Biswas

30. “Sky’s the Limit”

At its core, “Sky’s The Limit” is an incredible R&B song. When Biggie first heard the beat by Clark Kent, he knew he wanted it, even if he wasn’t going to put out Life After Death for another two years. He ended up recording three verses and a tongue-in-cheek “introduction” to himself. He got 112 to do the hook. If you lean in close, you can hear him quietly singing under their harmonies on the first chorus. 

Of course, the song draws comparisons to “Juicy,” and for good reason. If “Juicy” is Biggie’s autobiographical short film packaged into a rap song, then “Sky’s The Limit” is the blockbuster sequel. But unlike “Juicy,” whose warmth comes from the sort of handmade quality of the verses and production, “Sky’s The Limit” is stunningly refined. Clark Kent’s loungy R&B beat feels like a billowing fireplace in a mansion, and 112’s densely-layered hook envelops you like a warm blanket. Everything about it is indulgent and theatrical. 

Then come three verses that chart the career arc of a kingpin. Like “Juicy,” they seek to inspire, but they carry a much different tenor. Biggie sometimes alludes to success — “the only n***a with a mobile” — but doesn’t spell out the rags to riches story as directly as he does in “Juicy.” Instead, he pulls back, honing in on images that intentionally muddy the narrative: whether he’s really friends with his crew, smoking spliffs with “beginner-killers.” He’s still scoping out his clientele in the third verse, and doesn’t offer any closure about his rap career at the end. It all evokes a perpetual snapshot, or in its most extreme interpretation, a kind of alternate reality where Biggie didn’t have everything he dreamed of, and could only listen to old R&B records for hope. — Mano Sundaresan

29. “You’re Nobody (‘Til Somebody Kills You)”

Here, at Life After Death’s conclusion—remind yourself: this is the last song on the final Biggie album—“ You’re Nobody (Til Somebody Kills You)” leavens a double album full of instructions and rules with a woozy sing-a-long Irish wake of a hook and a pyre of ego, memory and easy technical accomplishment that recalls an fatalist gangster version of Sinatra At The Sands (Ed. Note: Or perhaps Dean Martin?).

 Even with the grace notes of gallows humor, the core subjects of Biggie’s final album remain as inescapable:  The indignity of death, the physical pleasures of life (“lavender and fuschia gators”), and an obsession with the posthumous. There’s one reading of the song as a simultaneous elegy for and criticism of Tupac. There’s another, broader reading that has Biggie conflating the fate of his own immortal soul with how he will be remembered by others: “You can be the shit, flash the fattest 5 / Have the biggest dick, but when your shell get hit / You ain’t worth spit, just a memory.”

If Tupac is Jesus in the New Testament, the vivid young man promising a world beyond this one, then Biggie is the collection of dead kings and Hebrew scribes of the Old Testament, slow and material and stoic. It’s no mystery: Puff Daddy reads sections of Psalm 23 to start the song. He leadeth me beside the still waters. Surely goodness and mercy shall follow me all the days of my life. And here, at the end of Biggie’s American century, you’re nobody until somebody kills you. — Evan McGarvey

28. “N***** Bleed”

Consider Arizona Ron. Or actually, first, let’s consider Sasha Thumper. She’s regarded as one of the great creations in one of the great storytelling songs ever made. And yet, she is a wholly passive character. She exists as a way for Andre 3000 to process his own shit. She gets a total of one line, in which she tells Andre she wants to satisfy the absolute base human survival instinct.

Now back to Ron. We know his taste in music. We know what city in Arizona he’s from. We know he came into quite a bit of money with his boys. We know the type of vehicle he drives. We know what language they speak in the country he absconded to in order to avoid the heat. We know of at least two pieces jewelry he wears and the cut of the diamonds on them. We know how he inked his gun wounds, and more importantly, that he’s the kind of guy who feels the need to commemorate his gun wounds with ink. And, much like Andre, we know how Biggie feels about life and his work using Ron’s mindstate as a window into his own.

I am deeply bitter that I’m not the first person to identify “N***** Bleed” as Elmore Leonard-esque (Kris Ex beat me to it by just four years), but really, what other comparison could you make? Where else in fiction would you find this sort of unsavory indelible character, bumping “Don’t Say Goodnight” out of his truck as he pulls up on a robbery/hit with a 5 gallon can filled with kerosene that was supposed to be gasoline? This is why Biggie transcends conversation that begins with Slick Rick and Kool G Rap and typically ends with Boots Reilly or Andre. He belongs in the realm of literary short fiction. Print this song in the New Yorker. He’s a master, and Arizona Ron is perhaps his greatest creation. — Abe Beame

27. Junior M.A.F.I.A. – “Get Money”

The year was 1996, and the Notorious B.I.G. had a few things he wanted to get off of his chest, namely women, money, and problems. And though he’s just one year shy of sharing how they all might correlate, he was then seeking solace in one and saying to hell with the others on a little song we all know as “Get Money.”

Before B.I.G. was rapping about “Mo Money, Mo Problems” in ’97, he unleashed his deepest woes with another mantra: “Fuck bitches, get money.” It’s the first line on “Get Money,” which was the second single on Junior M.A.F.I.A.’s Conspiracy debut LP, and places us right in the midst of a riveting spectacle narrated by B.I.G. and Lil Kim. Wrought with broken trust, accusations, infidelity, and violence, “Get Money” is a supposed tell-all of B.I.G.’s real life drama with then-wife Faith Evans (played in the video by the rapper’s then-girlfriend Charli Baltimore).

On “Get Money,” B.I.G. comes out swinging and leaves swinging, and Kim, who plays the subject of the late MC’s rage, bites right back. While she gets the final say (“Just a lil’ something to let you motherfuckers know”), B.I.G. has no qualms about just how hard his piece hits. When he says “Kick in the door, waving the .44 / All you heard was ‘Poppa don’t hit me no more!’” here and again on ’97’s “Kick in the Door,” he’s not trying to play the hero. While “Get Money” is nothing shy of a tour-de-force performance, there’s nothing sweet about this anti fairy tale. — Paley Martin

26. “I Love the Dough”

Biggie’s friendship with Jay-Z was like two movie anti-heroes who on the surface looked the same, but actually subscribed to two different schools of political thought. If Biggie is Frank White, the criminal coming home from jail and becoming the Robin Hood of New York, then Jay is Nino Brown, robbing and dealing his way to riches in the Reagan era. Frank White is trying to change the way the whole game works by giving back his money to the people. Nino is more cynical; he knows how the game works, and he is in it to get his. Biggie was the Jamaican from Clinton Hill who was Fat Chris in North Carolina and BIG to the rest of us.

On ‘’Everyday Struggle’’ he shouts out Rudy Giuliani and John Gotti, two white men on the opposite side of the law, because he knows that both of them, in their worlds, are the reason why black men are played by the system. BIG doesn’t jump off as a political rapper off the page because he is talking about politics within the framing of his American crime story, but only a racist and capitalist system could create someone like Biggie Smalls. Ditto for Shawn ‘’Jay-Z’’ Carter, who went from the Marcy Projects, to the trenches of Trenton and Maryland, to meeting the President. Jay-Z is from the era of Reaganomics. He saw what the crack epidemic did to his neighborhood and he never wanted to live like that again. 

‘’I Love the Dough’’ is the second song they made together. It’s the gloss to ‘’Brooklyn’s Finest’’’s grit. Gone are the lines about Biggie shooting your daughter in the calf muscle, now he is opening condoms while Jay-Z bags up some raw money from the block. Jay is in different form here than he is on Reasonable Doubt. That album is a crime novel from written by someone driven paranoid by the street. It is Henry Hill going through his crime life if he never snitched. On ‘’I Love the Dough’’, he became Iceberg Slim, joking on you for still driving cars that he forgot about when he first arrived in Trenton to start moving units. For an album that has production that feels as triumphant as a Knicks title would be, Life After Death is a dark album. When BIG mentions that he would rather be in the Carribean with Rachel Sands, he is thinking about a future without violence and beef following him. It’s a glorious dream that we can only wish happened. —Jayson Buford 

25. “Party & Bullshit”

As vivid of a portrait of the artist as a young man as rap has, “Party and Bullshit” first appeared on the soundtrack to 1993’s pleasantly forgettable, Who’s the Man?

The jewels of what would be Biggie’s mature style are clear here: the baritone that rumbles like a thunder storm but can snap into serrated runs of slant rhymes and alliteration  (“Pissy drunk off the Henny and skunk/ On some Brand Nubian shit beating down punks”); the menace underneath the party (“Fuck up the party before it even start”); a simple hook delivered wryly; flinty truth-telling without forgoing a modicum of joy.

Biggie, then a new father, only two years removed from a stint in a North Carolina jail, saw his preternatural talent catch fire in 1993. Along with “Party and Bullshit” came his verses on two Mary J. Blige remixes (“Real Love” & “What’s the 411?”). A savvy young Howard-dropout turned enfant terrible producer named Sean Combs plotted Biggie’s debut on the newly formed Bad Boy Records. For rap historians, “Party and Bullshit” is a treasure. For the listener, it’s the rare single that sounds like an actual party: discursive, sweaty, intense, funny and filled with the slick bullshit on which memories are made. — Evan McGarvey

24. “Long Kiss Goodnight”

A ‘’Long Kiss Goodnight’’ is BIG’s true Pac diss? ‘’Who Shot Ya’’ is a sinister monster, but it’s vague and was recorded before the Quad Studio shooting. It’s more of an omen that hasn’t yet come true. ‘’Long Kiss Goodnight,’’ however, is a scorched earth tirade. Puffy, finally not ‘’all up in the videos, dancing,’’ is in rare form here in the dunker’s spot, yelling threats like ‘’I prayed for you to stop! But you didn’t stop, so now we won’t stop!’’ while BIG smoothly brags about having Tupac Shakur assassinated. He mentions the song ‘’I ain’t mad at cha’’ while joking about how the slugs missed him the first time. 

As he kisses the beef goodnight, it starts to be deeply personal and dismissive at the same time like Pac was someone who was just a nuisance to them. They lack respect towards his soul. It’s just pure spite. Puffy’s rants take the form that Pac did on ‘’Hit Em Up.’’ It’s as disrespectful as it is ingenious, show-stopping as it is angry.

Besides Christopher, Bad Boy was hardly a company known for making murder music. Ja Rule was exposed for being corny but a company like Murder Inc. is ‘’connected’’ to more bodies than Bad Boy was. Bad Boy made their riches by making songs like ‘’Hypnotize,’’ which have great dexterity but are still accessible MTV Jams of the Week, the soundtrack at your Princeton graduation party. Over on the West Coast, Suge Knight’s Death Row Records were doing things a little bit differently. Puffy was encouraging Biggie to make songs like ‘’Juicy’’ while Suge definitely wanted his artists to get rich, but kept pitbulls in their Can-Am studios. He had a red carpet and cameras in every studio. Sometimes when you are in battle with whomever your enemy is, you have to become them in order to finally draw the dagger and end them. ‘’Long Kiss Goodnight’’ is the act of styling on the graves of your enemies, while using the fury that they once gave to you. — Jayson Buford

23. Jay-Z – “Brooklyn’s Finest”

With the notable exception of “Notorious Thugs,” Biggie’s collaborations usually find him firmly in his own lane, accenting a track with a husky Brooklyn verse or ceding some ground to fellow travellers like The Lox. “Brooklyn’s Finest” forces Biggie out of his comfort zone by making him contend with a rival talent who was at his creative peak.

The song is remarkable for many reasons, not the least of which is that Roc-A-Fella’s shoestring budget and Puff Daddy’s galaxy-sized ego allowed it to exist. It took some careful maneuvering by DJ Clark Kent to get Biggie and Jay-Z together in the studio for the first time. In 1996, Biggie had long since established himself with records that dominated New York while Jay sought to earn his place by shedding some of his more cartoonish, tongue-twisting rhymes and assuming the guise of the ultimate hustler; to this effect, Jay dressed like Bugsy Siegel on his album cover and rapped over luxurious jazz and soul samples. This new, ascendant Jay could rap as well as anyone in the city.

This isn’t the only challenge that faced Biggie. At his very best, Biggie uses the space of 16 bars to tell a story or create an intricate scene, but the back and forth structure of “Brooklyn’s Finest” limits him and Jay to four bar spurts — Kareem Burke recalls Biggie didn’t know how to count bars.

Under these constraints, Biggie raps some of the most memorable lines of his career. For every pithy Jay-Z verse, Biggie answers with an ice cold threat (“Shoot your daughter in the calf muscle”) or an iconic boast (“Trying to push 700s, they ain’t made them yet”) or biographical detail worthy of an epitaph (“Made my road to riches from 62s, Gemstars, my mom’s dishes”) or a now-infamous dig at his own wife. Ask hip-hop heads to quote Biggie and half of the responses will be lines from “Brooklyn’s Finest.”

With this song, Jay-Z showed he could perform next to the king without being overshadowed and Biggie showed that literally no one could rap better than him. — Evan Nabavian

22. “Goin’ Back To Cali”

“Goin Back to Cali” is a plea for de-acceleration of the East-West beef, an attempt to mend all fences, and a way of saying that Biggie just wanted to be loved and accepted for his incredible talent. It has some debt to LL Cool J’s 1988 classic of the same name, in which he debates leaving New York. But it’s a day for night reimagining. Rick Rubin’s skeletal track is dotted with horn stabs, and punctuated with record scratches, offset by a patient, fat riff. Easy Mo Bee’s production (Of course. Who else?) is a redeye, as in a cross country fight and a cup of strong coffee with a shot of espresso dumped into it. It’s almost impressionistically West Coast. The Rogers and Zapp P-Funk electro bounce, complete with talkbox hook, practically drives you to the boardwalk in Santa Monica for in-rhythm pullups.

The kid who made his classic album with The Chronic on his mind is equally impressionistic in his dedication to the state he was supposed to stand in opposition to. I was also a kid who grew up in New York and moved to California when I was just a touch younger than Biggie ever got to be, and his 90210 opening credits snapshot of the Golden State rhymes with the vague impressions I brought West with me. Impressions I picked up on two random visits there as a teenager, or in Big’s case, probably one or two West Coast swings promoting Ready to Die.   

Biggie’s approach is almost all conciliatory, flattering, even apologetic. Probably the one false note in his entire catalogue comes in the third verse, when he feels the need to tack on a few unconvincing threats to his would be and future assassins, mainly what feels like fanservice from the Bed Stuy product so his boys won’t shit on him for being soft (“I live out there, so don’t go there”, “I shall annihilate thee”). But the rest of the time, he’s making an incredibly sad and reasonable argument: That one dumb beef he didn’t ask for shouldn’t, and will not ruin an entire American coast for him. It’s a love letter. 

In the discussion around the new Biggie documentary that dropped on Netflix last week, I saw a critic question the intelligence of Biggie going to Los Angeles, to shoot the “Hypnotize” video, to attend The Soul Train Awards, to attend the Vibe after party at the Petersen Automotive Museum on Wilshire that fateful night, the last party he’d ever attend. To go back to Cali. How dumb/brave do you have to be to jeopardize your life in that manner, to walk into the lion’s den and practically invite your death? 

But I always understood the decision differently. It was made by someone who wanted to believe he could put the past behind him and start again, that 32 million people would collectively wake up and see how short sighted and immature and pointless this all was. Biggie understood the gravity of it all. Pay attention to the skit that opens the song, a wake up phone call from Puff confirming itinerary. Upon hearing LAX as his destination, a previously drowsy Big is instantly alert, “Oh, Cali?”, immediately understanding the stakes. Puff’s response feels like a return to life, a return to business, to reconciling with a market, a group of people Big and Puff desperately wanted to make peace with. Call it naive at worst, if you must. To me, it was nothing less than the humanist audacity of hope. — Abe Beame

21. “Ready to Die”

Hitting at a crucial juncture of Ready to Die, the album’s title track adds a ripple of spiritualism to the piece. If the cavernous gothic cathedral of “Victory” encapsulates a scaling up of the Bad Boy methodology three years later, “Ready to Die” feels set in an empty neighborhood church. Easy Mo Bee mixes Willie Hutch’s gospel organs with 1970s Blaxploitation guitars, a sound so deeply embedded in New York it was still seeping through the concrete in 1994. In this backdrop, Biggie pontificates on his crimes: “As I sit back and look when I used to be a crook/Doing whatever it took from snatching chains to pocketbooks.” There’s no remorse here because why fake it?

One of the batch of tracks Big recorded before Puffy was fired from Uptown, it encapsulates his early ferociousness. This is the Biggie Smalls spotted freestyling on the Brooklyn street corner in a colorful shirt, before he transformed into the smooth, Buddha-sized don. There is fire in his belly, iron in his larynx. If Big was ready to die, he was staring mortality down with not a single quiver in his voice. — Dean Van Nguyen

20. “Gimme The Loot”

There is a Reddit thread out there started by someone who genuinely wants to know who it is that Biggie raps with on “Gimme the Loot.” One the one hand, it’s grounds for the mother of all troll-based torchings. On the other, it’s a welcome reminder of something that those of us schooled in the Tao of Christopher Wallace take for granted- namely that more than a quarter of a century later, Biggie’s act of rapping with himself to play two seriously hepped-up stick-up kids is still jaw-dropping.

He wasn’t the first to do this – Slick Rick, Digital Underground, Positive K and Redman all had priors, but no one else embodied the characters the way Biggie did. They don’t just have different voices. They’ve got different flows. Different personalities. Hearing them amp each other up for some ultra-violence is suspenseful, hilarious and like all of Biggie’s best crime tales, profoundly disconcerting. It’s visceral in ways that previous gangster rap luminaries like Kool G Rap and NWA never quite achieved because Biggie’s gift as a writer and performer makes the pathology bleed through the speakers. They only need your rings and your necklace, but somebody’s gotta die. Hearing Biggie perform it, you can already tell who’s going to snap first.

Biggie uses this back-and-forth device to construct ever more outlandish and hilarious exhortations to violence. The third verse, after an extended beat break, is both excessive and entirely appropriate, while Easy Mo Bee’s beat is an act of sonic violence in and of itself, oozing menace and unpredictability. The drums sound like metal doors coming off hinges and a panicky flute mimics your heart rate as the gunmen bear down on you. The end result shocked both him and Puff so much that they bleeped out the word ‘pendant’ on the song’s climactic threat. “Gimme the Loot” is one of the hardest songs in rap history, a searing record of foul thoughts and fouler deeds worthy of Norman Mailer. — Joel Biswas

19. “Mo Money Mo Problems”

For the five years that I lived in Bed-Stuy, I’d stumble a few blocks to get my morning coffee and cross paths with the larger-than-life portrait of the Notorious B.I.G. on Bedford Avenue. It’d be 8:00 AM in the middle of winter and a group of at least three midwestern teenage girls would be holding out peace signs in front of the apartment building, to be geo-tagged on their Instagram accounts, of course. In the Spring of 2017, the slumlords of that very three-story complex threatened to remove the mural entirely — not because of neighbor complaints (which there were) — but because they wanted to add a couple of windows to increase the rent. They went on to hold the Biggie tribute hostage, demanding $1250 a month to not paint over it. Ultimately the realty group caved after numerous petitions aimed to educate them on Biggie’s importance to his borough — as if they didn’t already know. People celebrated, and the influx of Europeans, Midwesterners and guided Bed-Stuy tours still return to the corner of Quincy and Bedford to this day.  

That’s the genius with Biggie, Puffy and Mase’s “Mo Money Mo Problems.” The song frames putting up with the bullshit that comes with success, the pitfalls of fame and the influx of money in the most accessible if not optimistic of ways. The Diana Ross sample serves as the key soulful backdrop that stands in stark contrast to the beginning of Biggie’s verse — a nightmarish combination of investigations from federal agents, phone taps and keeping the gat close. You might miss that stress upon initial listens though because “Mo Money Mo Problems” was a direct appeal to Biggie’s bonafide pop credentials. He is undoubtedly one of the best lyricists to ever bless the microphone but his ability to transcend the genre for mass appeal went unrivaled for his all too short career. Diddy recognized that charisma, harnessed it, and what resulted was a song that will play on rooftops for every summer in existence until global warming renders the human race obsolete. By the time the Hype Williams-directed music video came out in all of its iconic fisheye lens glory, Biggie had already left planet Earth. Diddy and Ma$e rightfully decided to celebrate his life rather than focus on the bullshit. — Patrick Johnson

18. “What’s Beef?”

Who’s scarier? The simple answer is ‘Pac, the exposed nerve in leather daddy couture, the guy who says not once but twice in the first 20 seconds of “Hit ‘Em Up” that he fucked your wife. Pac is the henchman with crazy eyes, the one who licks the blade after he cuts your young ass up. The one who made fun of Prodigy for having sickle cell anemia. The one who eventually stops rapping altogether and resorts to screaming himself hoarse at every opp he can conjure up.

Then there’s Biggie, the one Faith Evans called a big teddy bear. His Sopranos comp would be Bobby Bacala [Ed. Note: The Sopranos related comparisons made by Jordan Ryen Pedersen do not necessarily — or at all — reflect those of the POW editing team], and nobody’s scared of the guy who cried after he had to kill the Canadian kid in the laundromat.

Then again. Biggie uses the Socratic method to dismantle his interlocutor. His voice is bemused rather than intense, which is unnerving the more you think about it. His cadence almost sounds like he’s skipping over the track. The first thing he does on his verse is laugh. It lulls you into a stupor, which makes the abrupt threat of Wayne Williams violence all the more jarring. It’s all supremely supervillain, Biggie as the laconic boss who pours you a drink before he cuts your balls off. Still sipping as your soul rises.

“What’s Beef?” isn’t even really a diss track. But in its studied nonchalance, the track would have infuriated 2Pac. You imagine him sitting in the studio fuming. “This motherfucker can’t even be bothered to get mad?”

Of course Pac never heard it. Somebody killed him six months before the song came out in March of 1997. “What’s Beef?” That’s one answer. –– Jordan Ryan Pedersen

17. “Machine Gun Funk”

Listen to “N***** Bleed” from 1997, and you’ll hear Biggie weave a crime tale in the mould of Raymond Chandler, full of suppressed anxiety and evocative detail that culminates in a climactic moment on a classic album — a counterweight to his glossy radio songs. On “Machine Gun Funk” from three years prior, Biggie is still a street corner rapper writing for audiences at hole-in-the-wall clubs in New York where Easy Mo Bee’s head-smacking drums and Biggie’s perfectly metered flow could induce heads to snap back and forth. It’s the song where he best demonstrates his street bona fides.

When Biggie yells out “Bed Stuy” or when he cuts out the beat and musters the force of a grenade launcher to say “Beating motherfuckers like Ike beat Tina,” you can picture the crowd screaming and spilling cheap beer on each other’s Avirex jackets. Easy Mo Bee says the iconic hook, a sample from the end of “Chief Rocka” by Lords of the Underground, was Biggie’s idea. (Note that the version of “Machine Gun Funk” on streaming services doesn’t slap as hard because Bad Boy had to remove an uncleared sample that brings the hook alive, but you can still find the original.)

This list will laud Biggie as a writer and a stylist, but he was a master of the intangibles too. “Machine Gun Funk” is explosive, a record that gratifies foul impulses and animal instincts. Play it when you’re allowed to be around people again or live vicariously through a 1993 performance at the Universal Zulu Nation anniversary. — Evan Nabavian

16. “Hypnotize”

Back in ’96, Puffy Combs made a phone call to Randy “Badazz” Alpert, the nephew of Cali trumpeter Herb Alpert, in an attempt to secure the sample from a 1979 number one record called “Rise.” This wasn’t the first attempt to clear the track. Cube, Eazy-E, and even Vanilla Ice had picked up the phone before and failed. But Puff sealed the deal after stopping by Badazz’s joint with Brooklyn’s finest, Christopher Wallace, to play a rare demo version of “Hypnotize” that featured the Notorious B.I.G. delivering both the bars as well as the girl’s hook — and inevitably blew his mind. 

Unsurprisingly, “Badazz” held on to that cassette. 

Sicker than you average, “Hypnotize” is a masterpiece in mafioso rap from behind Versace shades. Often misattributed to Lil Kim, Pam Long from Total flips Slick Rick’s sampled melody (La-di-da-di) on the chorus overtop a bombastic bass line, begging to be bumped with the windows down. 

Attempting the unthinkable, Biggie and Puff switched the 90’s rap narrative.  For a moment, the lyrical acrobatics riffing about robberies at gunpoint on the A train, open-air hand-to-hand crack deals on Fulton St., and shootouts with the NYPD, were put on pause. With sly wit and double entendres, B.I.G. conveys a crossover swagger, penning a love letter to his newly obtained lifestyle of the rich and famous. He expresses his penchant for everything from pink gator shoes, Persian rugs, escargot, Cuban link chains, expensive cars, to top tier oral from the outset—all the while hyping Bad Boy label mate and producer Puff as the Starsky to his Hutch. 

The music video for “’Hypnotize” archives the same maximal flexing. One of the most expensive and ambitious of the ’90s, it opens on a yacht in “Florida Keys” (actually shot in L.A.), and Puff kicks things off by literally throwing $100,000 stacks to the wind. Helicopters tear overhead like a hip-hop James Bond. There’s hummers, motorcycles, mermaids, and a high-speed car chase that has Puff driving a convertible in reverse to escape, while B.I.G. raps nonchalant without breaking a sweat. Leather bikini-clad dancers booty pop while a suited Biggie shoulder bops adorned with a megawatt smirk we’d rarely seen. As the screen pans to the finale, he’s landed himself a new female skipper from the pool party, and they’re riding the boat into the sunset in triumph. It’s a cliche that feels especially poignant: Biggie wouldn’t live to see the video’s final edit. —Tracy Kawalik

15. “Dead Wrong (Original Version)”

The prizes of being Sean Combs and surviving to tell the tale includes being unfathomably rich, your iPhone autocorrecting CIROC for you in the Verzuz comments, and being able to curate what’s at your tale’s center—history’s written by the winners, et cetera. If you’re Easy Mo Bee, sometimes you get written out of it. His subplot involves him producing the “Flava in Your Ear” remix; asking Diddy why did the credits read Sean “Puffy” Combs, Chucky Thompson and Easy Mo Bee,” when Chucky’s lone contribution was just being in the same room; and Diddy apparently taking offense at an honest question and distancing himself. Perhaps had Biggie lived to speak for himself, the idea that Easy Mo Bee brought out his hardest rhymes would be more of an obvious fact than a factoid.

You see this in Easy Mo Bee’s “Dead Wrong.” If the gothic loops on the “official” version served to lean into Biggie’s  horrorcore raps and Slim Shady’s cannibalism, it just fits the bill. But it’s not just how Easy’s dusted jazz production on the original cut inspired Biggie’s mayoral campaign. An effect of boom bap is how its abrasive drums forces a physical sense of place into your head. It gives Biggie’s menace an extra urgency. But “Dead Wrong”’s color mainly comes from Biggie’s words, which somehow makes a lucid character sketch of a jiu-jitsu practitioning bandit with baby bottoms as a swag reference point. — Brian Josephs

14. “Notorious Thugs”

In the mid-90’s, rap fandom was often self-defeatingly tribal. If you were from NY, Death Row were just pretenders throwing rocks at the throne, since they’d clearly peaked with Doggystyle and Dre was a spent force. Southern rap was another country that no one wanted to visit. As for Bone Thugs N Harmony, one snippet of their polysyllabic flows, sing-songy intonation and horse-drawn carriage performance at the 1996 VMA’s was enough to dismiss them as irredeemably wack and corny. Rappers from Cleveland? GTFO. 

Dead-set on national expansion and world domination, Biggie knew better. Just like its spiritual predecessor, Tupac’s All Eyez On Me, Biggie’s magnum opus, Life After Death, would flirt with hubris over the course of its almost two-hour running time, but ultimately pull off every one of its crossover bets –  and never more so than when Big Poppa hooked up with Bone Thugs.

The session for “Notorious Thugs” at LA’s Record Plant was a blur of intoxicants. Producer Stevie J, more accustomed to finding inspiration with some Malibu rum, made the beat while supremely faded from a blunt given to him by Brooklyn’s Finest. Krayzie Bone passed out in his car after too much Cristal and allegedly had to be roused into consciousness to record his verse. Layzie Bone had his weed “gangstered” by Big Poppa. But it was a success — Biggie loved what he heard and took it home to study before writing his verse, determined not to get murdered on his own shit. 

The end result was a revelation. Fifteen seconds in, Stevie J’s strip-club funk with its pop-ballad piano and Bone Thugz’ hook with its fly little refrain (“Get high… get high… get high…”) already sound anthemic. When Biggie rips into a new style of bouncing triplets inspired by his Midwestern collaborators, it’s little short of miraculous. We’re used to hearing that baritone sink into every groove of a track like molasses, but here he raps weightlessly, as lethally coiled as a cobra. Anyone who could do this had to be the best. Maybe there was musical life beyond the five boroughs. — Joel Biswas

13. “Suicidal Thoughts”

The most jarring part of “Suicidal Thoughts” is its vacillations. It begins with a barrage. “When I die, fuck it, I wanna go to hell.” But then Biggie eases off. Heaven’s probably like school anyway. They’ve got dice games and blow jobs in hell, and you get to wear black. Perhaps it’s just to make Puffy feel better, but still. (Puffy might’ve been all in the videos dancing, but his ad-libs on “Suicidal Thoughts” make a strong case for him as rap’s all-time best friend.)

Then the terror grips him, a boat in a storm thrashed by a wave. My mom would have aborted me. I got my baby mother’s sister pregnant. None of them will cry at my funeral. The self-loathing rising until he’s actually stuttering. Until he gets sick of talking and finally does it.

Biggie could do it all: the club tracks, the pop hits, the songs for the streets. But do we give him credit for doing all that, and also being a young Black man who spoke frankly about mental health? Sure, you can trace a line from “Suicidal Thoughts” back to “Mind Playing Tricks on Me” and forward to “XO Tour Llif3.” But what about #YouGoodMan? Biggie was talking about mental health two decades before Kid Cudi. Biggie wrote off “Suicidal Thoughts” in an interview as just the weed talking. It’s more than that.

It’s a cliché to call someone brave in a situation like this. Fuck it. If the shoe fits. — Jordan Ryan Pedersen

12. “Unbelievable”

“Live from Bedford Stuyvesant, the livest one/Representing BK to the fullest,” fires The Notorious B.I.G. to open “Unbelievable.” I’ve been thinking about why this is one of his most iconic lines. “Bedford Stuyvesant” is an undeniably sweet sounding set of syllables, especially when they roll off Big’s buttery baritone. And he’s coming at you “live,” instantly giving “Unbelievable” the brevity of classic New York hip-hop radio. Then there’s that descriptor: the livest one. Not the best one, the special one, the only one—the livest one. On an album swaddled in death, here was Biggie declaring himself live and kicking for Brooklyn, framed within a multi-syllabic rhyme.

No wonder “Unbelievable” was tacked onto the back end of Ready to Die, as far away from the bulk of the album’s narrative as possible.

DJ Premier was never one of Puffy’s Hitmen but here he was in the early days of Bad Boy helping to draw up the label’s blueprint: those jiggy keyboard chords and the boom-bap beat synthesized with an R&B vocal sample for that trademark smooth and polished yet smoky and funky sound. Then there’s the rapping. Put it this way, I couldn’t believe when the flawed biopic Notorious decided not to dub Jamal Woolard’s voice and instead let him spit Biggie’s rhymes. No disrespect to Woolard [Ed. Note: disrespect to Gravy, if not Woolard], but it was like asking Marion Cotillard to sing like Édith Piaf or Rami Malek to sing like Freddie Mercury.

You don’t have to be a hip-hop addict to know what you’re hearing on “Unbelievable” is special. Big transcends eras by dropping classic spell-your-name rhymes while also declaring Kwamé’s polka dot fashion craze “played out.” He declares himself “the illest,” “the nicest emcee,” “the triple beam dream.” Really, what’s left to say? Just one thing: the man was unbelievable. — Dean Van Nguyen

11. “The What”

Method Man didn’t listen to RZA. In 1993, the year Wu-Tang launched their consolidated storm, the Abbot decreed there would be no features on non-Wu projects. But Meth attended a music conference where he saw Biggie perform “Party and Bullshit” from the Who’s the Man? soundtrack. Post show, great recognized great. Meth then defied his shogun and joined Big, Easy Mo Bee, and Puff in the studio to record “The What,” becoming the sole feature on Ready to Die.

The middle track on the original version of the album, “The What” is one of the few songs unconcerned with narrative. (Big was so pressed for more autobiography, he narrated his birth on “Respect.”) Instead, Big and Meth trade some of the most heavily quoted bars in rap history, finding inventive, poetic, and hilarious ways to articulate sexual conquests and send competition to the ICU. You could write a thesis of Dickensian proportion listing and explicating every line, arguing over who bested who. Since this is a Biggie list, I’ll point to one of several favorites from him. Ever committed to the role, he purposefully hiccups before equating his abilities with both beautiful and devastating natural events: “Excuse me, flows just grow through me / Like trees to branches, cliffs to avalanches.” 

At times, Meth and Big were propelled by Easy Mo Bee’s slow and open beat, occasionally rapping over one another. The crackle of dust-caked vinyl pops between cavernous drums. It sounds like a NY studio ensconced in blunt smoke, your head and the room expanding and contracting in unison with the quasi-psychedelic melody. (Bee named the song “The What” as an homage to Miles Davis, who cared little for song titles.) The hook coheres about as much as the song, but “Fuck the world” is a timeless sentiment. It resonates at 16 and 60. Ever the shrewd (also read: probably stingy and perhaps predatory) businessman, Puff only paid Meth $2500. From a fiscal perspective, RZA was right. But “The What” endures because it captured two of the greatest on their ascent, knowing they deserved respect and compensation but still eager to earn it. — Max Bell

10. “Big Poppa”

The story goes that while making the quintessential New York rap album, Biggie had an ear to the West Coast. While Puff fed him the grittiest boom bap he could get his hands on, Biggie was bonding with producer Chucky Thompson, who’d come up from D.C., over L.A. hip hop. The pair ran the first Snoop album into the ground. They loved Dre and Ice Cube. They’d heard “It Was A Good Day” — who hadn’t? A cynic might describe them as opportunists, might point to the commercial dominance of “Regulate” that summer of ‘94, but nothing was planned. Biggie wasn’t ready for what Thompson would do next, and I’m not sure even Thompson was.

His concoction was shockingly simple: a syrupy flip of The Isley Brothers’ “Between The Sheets,” some basic drums and — the dagger — a preening keyboard melody that instantly transported the thing to L.A. Thompson describes it in interviews as an “experiment,” a way to get Biggie out of his comfort zone. As he tells it, the beat wasn’t as much an industry-coddled West Coast Rap Hit as it was a creative challenge. Why not?

Thompson left the room, Biggie entered the booth, and the Bad Boy Era was born.

I was first blindsided by “Big Poppa” on JAMN 94.5, Boston rap radio, as a throwback record. I couldn’t have been older than 9 or 10. Obviously I didn’t hear New York, or L.A., or any kind of context, really. All I heard was Biggie’s voice, auditory velour, and how the words seemed to seep out of him like a cold liquid. Even today, I think that’s the magic of this record. Like anything pulled from the Great American Songbook, “Big Poppa” transcends space, maybe even time. It simply is. It’s one of the three or four “gun to your head” Biggie songs. It carries all this regional diversity yet never feels like a rapper forcing a new style.

The clear explanation is that Biggie owned G-Funk so hard he made it his own. “Big Poppa” is a slithering pop song about sex and Moet and the club with a fear of death that, like “It Was A Good Day,” subtly transforms it into something deeper and sadder about escape. And yet, it never really feels that way. It’s an endless night. Biggie, for the first time in his recording career, is at ease. He isn’t rapping like he’s performing at a block party. He’s practically talking to you. Chucky Thompson unlocked his cooler, more dexterous side that you can hear all over Life After Death. It started as a challenge; it ended as metamorphosis. — Mano Sundaresan

9. Craig Mack – “Flava In Ya Ear (Remix)”

If you know the song, you know what it feels like. You’ve indulged in those first 13 seconds of anticipation, that small, suspenseful stretch of time that invites you to prepare yourself: the glass clinking, Diddy summoning Bad Boy to come out and play, the siren-like explosion, and those three head nod, stank-face-inducing bounces before the timestamp hits 0:14 and B.I.G. sets the track ablaze. 

Two years after signing with Bad Boy Records and two months out from releasing his Ready to Die debut LP, the Notorious B.I.G. introduced Craig Mack’s ’94 “Flava in Ya Ear (Remix)” with 16 punch-packed bars. The funny, braggadocious (“I get more butt than ash trays”) and shade-throwing (“don’t be mad, UPS is hiring”) verse deemed B.I.G. the track’s standout MC — even more so than Mack, who was the first and only other Bad Boy artist at the time. Assisted by the infectious Easy Mo Bee-produced beat (“I made that beat in my drawers”) and an all-East Coast lineup — Busta Rhymes, L.L. Cool J, and Flipmode Squad’s Rampage — B.I.G. and Mack put Bad Boy on the map through the Platinum-selling, Billboard-charting remix and what’s now rumored to be lyrical shots fired at one another.

Their alliance under the Bad Boy umbrella proved to be just as fruitful as their competitive bars with the The Diddy-masterminded, McDonalds-inspired B.I.G. Mack marketing campaign, which cleverly promoted both artists’ September ’94 debuts. Released within two weeks of one another, B.I.G.’s Ready to Die and Mack’s Funk Da World were both certified Gold and would represent the early building blocks of Bad Boy. Yet, just one year’s time would elucidate their disparate trajectories. In 1995, Mack would be dropped from the label and B.I.G. would be the top-selling male solo artist and rapper on the US pop and R&B charts.  

As history would have it, the “Flava in Ya Ear (Remix)” was the beginning for one, the beginning of the end for another, and an early warning sign that B.I.G. Mack would quickly fade to just B.I.G. —Paley Martin 

8. “Kick in the Door”

Rap reminds me so much of pro wrestling. It’s subjective art presented as an objective, competitive sport. There are a lot of people playing a role even though the most successful practitioners simply amplify their natural personalities to an unreal wattage. Alpha male posturing is the order of the day. You spend your life trying to reach the top, but it’s more difficult to stay there. Imagine building a house on a mountaintop and having to protect that house every day as worthy and unworthy contenders try to knock you off. 

“Kick in the Door” was Christopher Wallace’s acknowledgement that he was the number one guy in the business, and a challenge for anyone to step to him if they wanted that spot. Nas famously contended in 2004’s “The Last Real Nigga Alive” that the song was a shot directly intended for him; if you subscribe to that theory, there are obfuscated references to It Was Written adopting Ready to Die’s glitzy, widescreen approach to cleverly plotted hood stories. 

For everyone else, “Kick in the Door” was a thunderous reminder that exorbitant success and smooth, poppy chart-toppers had not softened the man who once threatened to jack a pregnant woman’s #1 Mom pendant; Biggie was still the bull of the woods as far as rapping was concerned. Opening with the hysterical introduction to the iconic Madd Rapper, starving artist du jour still struggling after the release of his fourth album — host Trevin Jones calmly reprimanding him for his language is what puts this in the pantheon of truly unskippable skits — DJ Premier launches into an all-time great Screamin’ Jay Hawkins flip and Big strides in as the kid bullying and embarrassing every other rapper who had ever stepped into a cypher with him.

When The Source awarded Life After Death their coveted 5 Mic rating, the first verse of “Kick in the Door” was given the Hip-Hop Quotable for that month. Its third verse was like a grenade going off in the middle of The Tunnel. The entire song serves as the Dead Sea Scrolls for every generation of rap thereafter. The Johnson & Johnson line singlehandedly created the coke-rap subgenre. “Your reign on the top was short like leprechauns” may be the greatest opening line of any song since “Ground Control to Major Tom.” That thing Madlib does where he samples standup comedians? Its antecedent is the voice of Martin Lawrence before this song kicks in. I’m sure there were rappers who didn’t even know they had to recoup the money advanced to them by labels before Biggie taunted them with the song’s final line.

Everything about Biggie we loved as the GOAT MC is crystallized on “Kick in the Door” in illuminating detail: He weaves in and out of rhyming sounds like he’s in the NFL Combine, he offhandedly brings in his penchant for fatalism (“Look how dark it get when you’re marked for death”). He’s self-referential, his wit is whiplash quick (if you come at the King of New York with disrespectful views, you’ll be reading all future rebuttals in braille), he states facts without embellishment or any sort of varnish right alongside his most outlandish exaggerations. After Big’s death the rap game fractured severely, so when he said, “Ain’t no other kings in the rap thing,” the comment wasn’t a throwaway boast, it was prophetic. — Douglas Martin

7. “10 Crack Commandments”

Crack cocaine has personality and history. Crack cocaine isn’t only a drug that became an epidemic, it also became the backdrop for a generation of policies that ravaged an entire community. Mandatory minimums, ‘’community policing’’, and even stop and frisk are because of the war on drugs. Crack cocaine, because it is a drug that is predominantly done by Black and poor people, was given ‘’boogeyman’’ status in America. No one calls it the cocaine epidemic, or the quaaludes epidemic. White historians call it the crack epidemic because it is a widespread phenomenon of Black people being lowlives to them. They only think about the crime but not the fact that white supremacy, like poor education systems and capitalism, is the reason why the crime exists. 

The Notorious B.I.G. saw crack all over the borough of Brooklyn growing up. Born in 1972, he was a bit young for the Reagan era but the first Bush era is still ‘’crack city.’’ He saw it being used and then because of poor education systems, the allure of riches, and over policing, the one promising schoolmate became a drug dealer. The reason BIG’s rapping about drug dealing was so unique was that it also had a twinge of pain to it. In the third verse of ‘’Everyday Struggle’’ he talks about seeing the urban decay (‘’dealin with the dope fiend binges, seeing syringes’’) around him has him struggling to stay upbeat and maintain his faith. Detectives know that his first name is Christopher; but his TEC is going to override their small time guns.

However, BIG could also brag about how good he is at selling drugs. He could be a bad teacher, showing the kids how to cook crack like he was the substitute teacher that didn’t get vetted by the principal. On ‘’Ten Crack Commandments,’’ he was exactly that, going through the steps of the drug world like he was Moses who wore Timbs. Just like Moses, BIG feels like he is having an experience that has come from God.

Crack is a set of rules in place for you not to get your wig pushed back. With intense precision, BIG puts you on to game, while also making you fear the game. He mentions that you can’t trust anyone; your mom might set you up if she is gassed up enough. There is no credit in this game because a drug addict will never pay you back. What’s the most important rule on this list? Is it ‘’never let them know your next move: don’t you know bad boys move in silence and violence?’’ Or, is it ‘’if you don’t got the clientele say hell no, cause they gon’ want their money rain sleet hail snow?’’ It doesn’t matter. All that matters is that if you are going to join this game, you have to know the rules of the streets. — Jayson Buford

6. “Things Done Changed”

Christopher Wallace was barely out of his teens when work began on Ready to Die, but he never sounded that young. When Wallace gave life to his alter ego The Notorious B.I.G., it was the vision of a man who had witnessed similar hardship without any of the love. Voletta Wallace was an iron-willed mother, who as a young woman emigrated to New York from Jamaica in the hope of siphoning off her own section of the American dream. She worked hard to shield young Christopher from the dangers outside their  door on St. James. The Notorious B.I.G. received no such protection: it’s right there on Ready To Die’s “Intro,” which features a mother portrayed as unhinged and irresponsible, nothing like the woman whose sternness cast fear on the local villains who sometimes hung with her son.

The album’s first real song, “Things Done Changed” sets the scene in pulpish detail. Our protagonist, returning home from prison, juxtaposes a nostalgic, sepia toned vision of the Brooklyn he grew up in—a Brooklyn of barbecues and kids playing in the streets with no fear, where scores were settled with fists not guns—with horrible new realities. It’s a masterpiece in vista building, our anti-hero laying out his insular world with diamond detail, the hustle and flow of gangster rap shed of all glamor. This is the fulcrum on which the entire Biggie narrative—the entire Biggie legacy—leans.

Yet greatness often includes things you can’t explain, like how the beat is credited to one Darnell Scott, who as far as I can tell never produced another major song. The blaring horns, tough drums, and dreamy flourishes that move mournfully but with urban cool. Cutting vocal samples of Biz Markie and Dr. Dre together is a perfect moment of East Coast-West Coast fusion, reminding us that hip-hop on both coasts was once united in depicting ghetto living. And like a lot of coke movies on wax, reality is spliced into the narrative: “If I wasn’t in the rap game/I’d probably have a ki, knee-deep in the crack game,” says the man who had spent nine months behind bars after being arrested in North Carolina for dealing with no means of making bail. Then Big famously drops a detail about his mother’s cancer, a moment when the persona melts away, and reality overwhelms his widescreen crime epic. — Dean Van Nguyen

5. “Warning”

A 5:46 wake-up call only brings bad news. The streets are full of lethal shadows; crust covers your eyes and cobwebs clog your head. Nocturnal sweat and liminal nightmares reign. Those final pre-dawn minutes mark the last rumble of ungoverned chaos — when the news of fatal accidents and cloak and dagger schemes trickle in. When the pager blows up, it always contains those doomed numerals: 9-1-1.

“Who the Fuck is this, paging me at 5:46 in the morning”

“Warning” is a three-act play, but a one man-show. Biggie stars as both the protagonist and Pop from the Barbershop. Distorting his voice via the muffled fuzz of the telephone wire, Pop bears the details of an assassination plot. Some stick-up kids from Brownsville heard about it all: the $10,000 watches and the luxury sedans with Lone Star plates, the stash house in the same neighborhood as congressmen and John Thompson (RIP), and even the home in Florida purchased for Voletta. Lil Fame of M.O.P. brought the warning, and now, the transmission is complete. Clutching the mac, Pop bellows:

“Tell me what you gonna do!”

The noir themes and conceptual ambition of “Warning” are replete throughout Biggie’s catalogue. “Get Money” and “Somebody’s Gotta Die” evoke similar paranoia and the preemptive desire for revenge. “Gimme the Loot” finds him ventriloquizing the other stick-up kid. But “Warning” is the masterpiece, a tautly sketched narrative of meticulous syllable placement and dense writing, chilling imagery and cinematic three-dimensionality. The Black Alfred Hitchcock dialing m for murder, Rottweilers by the door, bellies bloated with gunpowder.

The tradition of multiple overlapping narrators wasn’t new in rap. In some respects, Biggie expanded on the innovations of Rammellzee and K-Rob. Only 18 months prior to “Warning,” Positive K — the Big Daddy Kane collaborator from the Bronx — scored a novelty hit with “I Got A Man,” rapping as both aspiring Don Juan and the scornful target of his affection. But Biggie cast a tense and virtuosic spell. A lurid imagination running wild. Ironically, Kane himself first passed on Easy Mo Bee’s flip of Isaac Hayes’ “Walk On By.” When Puff heard it a few months later, he went crazy.

No one conveyed so much in so few breaths. The twin 16s of “Warning” barely exceed 450 words. It’s one of the greatest short stories ever written, from the first few bars yawning and wiping the cold out his eyes. It shares the conclusions of “Mo Money Mo Problems,” written three years later. Few want to kill you when you’re clocking minor figures, but with the arrival of money and fame, he’s both a piggy bank and a precious scalp. His language leaves bloodstains: “they wanna stick the knife through your windpipe slow.” The hook seems almost too weary and exasperated for a 21-year old to have written it.

“Damn, n***as wanna stick me for my paper”

You can see the impact on Jay-Z, whose “Can I Live” chorus, later repeated the formula to poignant effect. This is part of the brilliance of Biggie, the blend of linguistic complication and graceful simplicity. A few lines later, he elaborates: “Damn, n***as wanna stick me for my cream/And it ain’t a dream, things ain’t always what it seem.” In a single sentence, he peels back the tangled reality undercutting “Juicy.” Heavy is the head that wears the tilted crown.

Other rappers would stick to unleashing a terrorist litany. Biggie prophetically unveils visions of “slow singing and flower bringing if his burglar alarm starts singing.” It’s the way he turns “burg-lar” into bur-gah-luh,” the pacing a somber death waltz to match his intent. And just when you think he’s getting a little too flowery, he will “fuck around and get hardcore, C-4 to your door, no beef no more.” It’s unclear whether he’s ferociously planning his reprisal to Pop, or if he’s saying this all to steel his own resolve. Then, just as he cocks the gun back, he hears footsteps.

As with the best storytellers, Big purposely leaves out details to haunt your imagination. We hear the whispers of the home invaders.

You sure it’s Biggie Smalls crib, man?
Yeah, I’m sure, motherfucker, come on
Man, fuck, this better be his motherfuckin’ house

The jackers get their confirmation, but only after spying the infrared dots on each other’s foreheads. Biggie’s wide awake; but for them, it’s a little too late. — Jeff Weiss

4. “Who Shot Ya”

Biggie was a master of subtext. His stories were deflections that alluded to broader themes. “Juicy” is a rags-to-riches tale as much as it chronicles hip-hop’s rise. Yet it’s also a song about growth and acceptance. That’s why “Who Shot Ya” struck such a deep nerve despite being a B-side to the ubiquitous radio smash, “Big Poppa.” This was ‘94 and something bigger was afoot. It bolstered Biggie’s claim as East Coast king at best, and an instigator at worst, stirring fans’ imaginations, but also that of Tupac, resulting in the legendary diss from on high, “Hit Em Up.” In it, Shakur straight up named names. 

Of course we now know the subtext to “Who Shot Ya” never existed. Never was it a brazen jab at Pac’s Manhattan shooting weeks prior despite some media saying it such. Pre-internet era gossip became make-believe and the resulting coastal beef of Mount Rushmore-proportions was something to behold. People liked making hand symbols amidst a bi-coastal war. The hook didn’t help either because it felt like a deliberate taunt. But that just spoke to Biggie’s natural ability to draw you in and make it feel personal. “Who Shot Ya” was in fact recorded well before Pac took five bullets to the head and body. To no one’s chagrin— and perhaps to everyone’s eventual detriment—record sales ballooned. 

Many distractions orbit the song but at its core, we’re left with morose piano clinks from a brilliant David Porter loop, and familiar Biggie rhyme schemes: “I make your skin chafe, rashes on the masses. Bumps and bruises, blunts and Land Cruisers.” It’s celebratory yet kind of dim. Very ‘90s with a Sopranos-esque timelessness, extra large button-ups and plump cigars. The song’s enduring impact just speaks to Biggie’s magnetism, the result of an imposing voice and unmatched way with words. He made it look easy and so hard at once. Rap’s most misunderstood track is forever tethered to unsolved murders which, decades later, now feels unsettlingly self-referential.  — David Ma

3. “Juicy”

It pushed the Sega Genesis’ lifespan another 25 years and counting. It’s the best path to ensure a media brand’s longevity—not behind a paywall or in the hands of private-equity ghouls, but at the 22-second mark of Track 10. It’s your 12th birthday and you know your mother lied about that sparkling cider in your flute being champagne to make you feel grown. Didn’t matter: Everyone wanted a piece of “Juicy”’s story to be theirs.

There’s a subgenre of writing dedicated to praising “Juicy” and another subgenre dedicated to saying “What more is there to say about ‘Juicy’?” Has there been enough written about its audacity? The throughline of Ready to Die’s intro besides Biggie’s eyes is how the innocence of listening to “Rapper’s Delight” gave way to soundtracking surviving ‘90s New York. Yet “Juicy,” sequenced near the album’s center, carries none of that fatalism. He runs through the plagues America funnels to Black communities—dropping out of high school, predatory police and complicit neighbors—and doesn’t really even posit them as ills we ought to be fighting. But when Biggie claims “Stereotypes of a Black male misunderstood/And it’s still all good,” he’s not pushing a blind hope out into the universe. It’s a pronouncement. Even repeating that line in earnest feels defiant. 

Of course, “Juicy” being a solely Bad Boy achievement depends on who you ask: Pete Rock said Diddy heard him flip that Mtume sample at his house and bit it. This isn’t to say you should steal from the dude who produced “The World Is Yours,” but you can immediately sense something’s been lost in his take even if you can’t put a name on it. Pete’s metallic percussion draws Brooklyn’s physicality and hems you within it; Poke and Diddy’s bounce lifts “Juicy” just above those buildings and into that space between reality and aspiration—a space those within earshot crave with the ding of that first note. For Bad Boy, it’s an early hallmark of what we know became a winning formula. For the entirety of American art, it’s as neat of a bow as you can place on hip-hop’s most gnawing contradiction: Biggie’s murder made the culture inextricable from death, and yet his biggest song was literally a paean to life.–Brian Josephs

2. “I Got a Story to Tell”

Some short hand from sophomore year poetry still holds up: if the narrative is concerned with “recollection,” then the lyric is all about “recreation.” Is what you’re hearing a memory or an attempt to recreate an action itself?

“A Story To Tell” starts with seduction, turns on an impromptu robbery, and ends with a spoken word retelling of the night to friends that takes up half the song’s length. At the moment when the anonymous New York Knick [Ed. Note: The God Anthony Mason] is about to stumble upon Biggie and the man’s girlfriend and Biggie pretends to be robbing the couple as a cover, Biggie recalls the moment of inspiration simply:  “It came to be like a song I wrote…”

Yes, you could put together a diagram how the song plays with the elements of the classic dramatic monologue and autopsy the differences between the scene as Biggie raps it in the beginning and the story as he tells it to his friends, but you can also linger in the song’s uncomplicated pleasures. Revel in the insouciance from the simultaneously horny and  “gat in hand” speaker. Enjoy the tossed-off phrases that other rappers would give their eye-teeth for: the charisma in “Sweetness, where you parked at?”; the phonetic thrill of “Put stacks in a Prada knapsack; hit the door.”

In three minutes, The Notorious B.I.G. cuts through the binaries of singing versus storytelling, cooing to your lover versus laughing with your friends, retelling something versus reliving it. The results are prismatic, electrifying, and emblematic of the best MC ever in total control of his lyric and his narrative instruments. — Evan McGarvey

1.”Everyday Struggle”

How do you write about an entire generation? In 1994, the year Joe Biden’s Crime Bill was made law, it was the final piece of an American project to addict, destroy and incarcerate its young Black population, and “Everyday Struggle” encapsulates the daily minutia of this quasi-genocide not in the political terms of a Public Enemy nor the nihilistic ones of Eazy E, but in a deeply personal 3 act story.

Before we even get to the words however, we have to make sense of music that conveys the exact opposite of a struggle: a breezy, floating soft jazz loop by a man who thought it wise to be photographed lounging in a cowboy hat. It sounds like the coolest on-hold music you’d ever been subjected to, at least until the hardest drums this side of RZA barrel through and take center stage. I’m not one for overthinking musical arrangements: 99% of the time, they don’t “mean” anything – they just sound dope. But if you wanted to make a case for this contrast between rhythm and melody representing the ups and downs of the drug game, subjects explored in detail by Biggie throughout the song, I wouldn’t begrudge you. In any case, it’s worth taking a moment to salute The Bluez Brothers – Lord Digga of Master Ace Inc. and Norman Glover – for delivering the greatest beat on a perfect album.

Most of Biggie’s later crime capers are either fictional or at the very least exaggerated. 

He had a brilliant mind for cinematic detail, one briefly deployed here to describe his partner Two Techs (cause he hold two techs). Yet “Everyday Struggle”, is frighteningly real and brutally honest. From the shame of drug dealing on his neighborhood corner, to the thrill of escaping poverty by hook or by crook, to the paranoia and stress once he’s too deep in the game, Biggie describes not only his own rise and fall, but that of countless other young Black men of his generation. Because he’s lived it, he casts no judgment but also makes no excuses: the everyday struggle is at once his lot in life and the way he takes agency for his future. Scholars, writers, and politicians have spent the past 40 years deconstructing the drug game and revealing just how it destroyed a generation: Biggie does it in under six minutes.

And yet for all of its specificity, Everyday Struggle is a deeply universal song. A lot of that is down to that hook. ‘I don’t want to live no more’ is as universal a sentiment as can be, a solemn statement that life doesn’t always feel like it’s worth living, particularly when drugs permeate every facet of your existence. In a parallel universe, fellow 90s hero Kurt Cobain could have written it while Biggie could have exhorted listeners to load up on guns and bring their friends. Ultimately, it’s the song’s contractions – the beauty of its loop next to the roughness of its drums, the shame and paranoia of drug dealing next to the high of the hustle, and the desperation of that hook next to the brilliance and talent of its writer – that make it Biggie’s single greatest statement. Life is tragic and sad and brief and beautiful and it makes no fucking sense. “Everyday Struggle” understands that. — Son Raw