Image via Kool Keith/Twitter

Independent rap journalists will recommend you new music until their voices give out. Keep it that way by supporting Passion of the Weiss via a subscription to our Patreon.

Pete Hunt is still trying to figure out a justification for posting a link to Celly Cel & UGK’s “Pop the Trunk” on LinkedIn.

You can divide Kool Keith’s career into three distinct eras.

We start with the Ultramagnetic age, spanning roughly 1984 to 1993, during which Keith leads a ragtag crew of Bronx surrealists to underground success, develops an entirely distinctive and still unduplicated flow, and predictably departs the group for a solo career. Next comes the Dr. Octagon phase, say 1994 to 1999, wherein Keith’s interstellar gynecologist drops an instant classic album, Keith himself is briefly signed to DreamWorks, and electronica acts come calling for guest verses. And finally, there’s the everything-after-period, roughly 2000 to right this very second, featuring a Mark E. Smith-like volume of scattered releases, belated sequel projects, and steady touring as a nostalgia act.

If you were putting together an all-killer, no-filler greatest hits album (think Immaculate Collection, Legend, Substance), you would naturally gravitate to the first two eras—say a handful of Ultramagnetic bangers, four cuts from Octagonecologyst, three cuts from Sex Style, “Diesel Power,” “Get Off My Elevator,” “King of NY,” and a smattering of songs from Dr. Dooom and Black Elvis.

But what if that greatest hits album suddenly expanded into a two-disc, career-spanning anthology? (Think of all those “Essential” collections your old man kept in the garage CD rack.) Could you pull from those late-era Keith releases to assemble a collection of cuts for Disc 2 that matches the magic of Disc 1, banger for banger?

Reader, we wouldn’t be here together if I couldn’t answer that question affirmatively. Digging through these records is no easy task, though. Keith has put out at least 30 albums since Black Elvis, his last release with a major label, dropped in 1999. Just last year alone, he released a solo album (Keith’s Salon), a collaborative album with Del the Funkee Homosapien (Subatomic), an EP (Donovan the Don), and 20+ singles, guest appearances, and remixes. He’s been a little quieter in 2022, with only one EP and a handful of singles, but it’s still a tremendous volume of work to assess. Buried within, though, are total gems that deserve to be showcased alongside his better-known hits.

Below, we cover the 20 best Kool Keith songs from the past twenty-two years in roughly chronological order, with a few leaps across the timeline here and there for comparative purposes. You can find a Spotify playlist that tacks on a few extra tracks here. Astroglide, time machines, and ovum forceps are sold separately. Let’s get going!

“Analog Technics (feat. Odd Oberhiem)” – From Pimp To Eat (2000)

Analog Brothers was a collaboration between Keith and Ice-T, along with affiliates Marc Live, Black Silver, and Pimp Rex. The “supergroup” hook ensured that their debut album, 2000’s Pimp to Eat, received decent press coverage for an independent release, though it ultimately failed to attract a larger audience. Keith is in vintage form throughout, adopting the rock star persona of Keith Korg and imagining himself “headlinin’ over Toto and 702, Lil’ Kim, and Foxy” on a world tour “supported by Budweiser.” Ice-T is just as comfortable in high camp mode, and he fully inhabits his futuristic pimp character, Ice Oscillator (who sounds like someone Ice’s Law & Order detective would have arrested for sex crimes). The production, per the title, is driven by analog instrumentation, meaning lots of Moog synthesizers, thick 808 drums, and John Carpenter vibes. Everyone’s having a good time here except the listener, as the album really drags at 60 minutes. Still, there’s an EP’s worth of strong material, most notably “Analog Technics,” which features a strong verse from Black Silver complete with an era-specific Sega Saturn reference.

“The Bay/Bronx Bridge” – From Masters of Illusion (2000)

“We All Over” – From Masters of Illusion (2000)

Motion Man (né Paul Laster) had come up in the East Coast underground rap scene—he was a frequent guest on Sway & King Tech’s Wake Up Show—and could seamlessly alternate between battle-ready bars and more playful flows, especially when imitating other rappers or adopting different personas. This versatility made him the perfect partner for Keith’s imaginative lyrical escapades. The two first collaborated on skeezy Sex Style-cut “Sly We Fly” and then again on Black Elvis‘s “Clifton” (where Motion played chulo rapper Clifton Santiago). The full-length Masters of Illusion followed soon after with KutMaster Kurt behind the boards. Motion Man again displays a dynamic range, helping Keith spin a Rae & Ghost-like crime tale on “We All Over” and switching to an Ultramagnetic cadence for “Bay-Bronx Bridge.” These two cuts are arguably the best on the album, but the whole thing is a solid listen with top-shelf production from Kurt throughout.

“Wedgie” – From Dopestyle 1231 (2004)

“Diamond District” – From Project Polaroid (2006)

Bay Area producer TOMC3 was a KutMasta Kurt understudy whose sample-heavy, full-bodied beats were a direct descendent of Endtroducing… and Dr. Octagonecologyst. His first project, 2004’s Dopestyle 1231 album with MC Dopestyle, seemed custom-made for college radio, especially with track titles like “I’m Grendel” and “Little Grasshopper” and guest spots from Del the Funkee Homosapien, Vast Aire, and (naturally) Kool Keith on the excellent “Wedgie.”

Project Polaroid, a full-length collaboration between TOMC3 and Keith, followed two years later. The album is presented as a soundtrack to a 60s spy flick, and the samples seem to pull heavily from scores from that era. Keith is in peak free association mode, riffing on everything from Mike Piazza to Burt Lancaster to Black Israelites, and briefly surfacing from his fugue state to condemn a decadent record industry (“everybody who’s a demon hang your coats on the rack / half the companies make billion off of Biggie Small and Tupac prototypes / people want to remove the devil horns off the top of their heads / move it to conscious rap / and stab you while you’re not looking right in the back.”)

Fans will note the lack of X-rated references here, which was an intentional choice. “I told [Keith] that I was looking for him to do some sci-fi and off-the-wall stuff,” TOMC3 told an interviewer, “but I didn’t want him to curse as much and use his typical vocabulary. He said, ‘I know what you’re looking for’ [and] responded with what you hear on the album!”

Project Polaroid is by far the best Keith release from the 2000s, and if it had dropped even five years earlier—when the 90s underground sound was still in vogue—it would be spoken of in the same breath as Dr. Octagonecologyst and Sex Style. This was the Hell Hath No Fury-era of blog-hyped rap, though, and there wasn’t a lot of critical appreciation for throwback projects. Tracks like “Space 8000,” “Diamond District,” and “Clubber Lang” are highlights, but the whole album is a slept-on classic that deserves to be heard from front-to-back.

“Trees” – From The Return of Dr. Octagon (2006)

“Area 54” – From Moosebumps: An Exploration Into Modern Day Horripilation (2018)

Keith had a contentious relationship with his most famous alias, Dr. Octagon. That project had initially emerged out of demos recorded with longtime friend and producer KutMasta Kurt. Dan “The Automator” Nakamura immediately latched onto the concept and worked with Keith to create an entire album around the character. Kurt retained production credits on two songs (“Dr. Octagon” and “Technical Difficulties”) but never felt adequately recognized for his contributions and eventually sued for proper royalties.

Keith, likewise, didn’t feel that Dan had given him enough credit on the project, and also seemed uneasy with being stereotyped as an alternative sci-fi rapper. (“You see me coming into the office with Macy’s bags but you gonna make me wear a robot suit?” he complained to Fact magazine.) Whereas lesser artists might set this animosity behind them, Keith’s 1999 First Come, First Served album begins with his new persona, Dr. Doom, blasting away his old one with a shotgun.

This twisted Bergman allusion didn’t stop Keith from announcing an Octagon sequel in 2002, this time backed by Stones Throw-affiliated beat maker Fanatik. Unfortunately, the project dissolved in a legal stand-off between rapper, producer, and label. The recorded vocals were eventually passed on to a menagerie of producers operating under the billing One-Watt Sun, and this crew was able to finish the album with Keith’s limited involvement. After years of speculation, The Return of Dr. Octagon finally dropped in 2006. (This timeline ignores the cash grab Dr. Octagon Part II album released by a fly-by-night label.)

The critical reception for Return of Dr. Octagon was luke-warm to positive (Rolling Stone called it a “messy, gloriously weird sci-fi hip-hop record”), but hardcore fans hated the album’s production, which sounded beamed in from a glitter-heavy Eurovision performance. Rather than returning to Automator’s haunted soundscapes, One-Watt Sun seemed to take their cues from “Abandon Ship (Sharks and Mermaids),” Keith’s Amp 2-era collaboration with underground rave group Hardkiss.

Lead single “Trees” is surely one of the earliest examples of hyperpop, with layers and layers of slinky synthesizers, glitchy guitar sounds, and chopped-up vocal samples, all doused in neon and marked as urgent. The rest of the album is similarly disjointed, both sonically and thematically. “A Gorilla Driving a Pick-Up Truck” is about exactly that, with Keith adopting a CB radio voice and mumbling about a primate “chewin’ bananas, wearin’ a bandana” chasing him down on an unnamed interstate near Texas. “Al Green” seems like a series of subliminals aimed at André 3000, with Keith criticizing “muh’f*ckers, grabbin’ a guitar / like they Tracy Chapman or some sh*t” and dressing “like they from Pakistan” over a stuttering disco beat.

The Return of Dr. Octagon is not a great album, but at the time it felt like a refreshing left-field turn from an artist whose experimentation had grown stale and predictable. And since fans were always going to criticize a sequel album that didn’t return the original cast, why not crank the weird up to 11 and try something different? Alas, contemporary audiences in 2006 (the year Crash won Best Picture) weren’t ready for this forward-thinking art.

The formal Dr. Octagon sequel, Moosebumps: An Exploration Into Modern Day Horripilation, finally arrived in 2018, and once again paired Keith with Dan the Automator and turntablist DJ Qbert. It’s a respectable effort with a handful of vintage Keith performances (especially on “Area 54”). But it’s also total fan service. Real heads secretly prefer Return of Dr. Octagon‘s uncompromising eclecticism. Trees are dying, ya’ll.

“Prepare” – From Sex Style: The Un-Released Archives (2007)

Dr. Octagonecologyst was often described as “horrorcore” due to Keith’s lyrical allusions to gruesome medical procedures and deviant carnality. But Dr. Octagon was clearly a character, whereas Sex Style presented an unfiltered look into the mind of the real Keith Matthew Thornton, and the result was a far more transgressive artistic statement.

Given that the album’s thematic focus was so closely aligned with Keith’s real-life interests, it shouldn’t be surprising that the recordings from that era produced so much extra material, much of which was released on the 2007 album, Sex Style: The Un-Released Archives. The compilation’s first and best song is “Prepare,” which would have been a standout cut on even the original album.

Prime Keith was like J.G. Ballard penning Penthouse Forum letters, and his gifts as a writer really shine through here. “I got lotion to pump and more Vaseline / My fantasy to freak a honey using gasoline.” “Yeah, I’m standin’ naked in the bathroom / Sweepin’ your panties with a dustpan and broom.” You would never hear little scene-setting details like this in rhymes from say, 2 Live Crew. A better comparison is probably Prince (or maybe Peaches), but honestly no musical artist has ever captured the VHS porn aesthetic quite as vividly as Keith.

“Mechanism Nice (Born Twice)” – From The Best Kept Secret (2007)

Kool Keith was the ordained star of Ultramagnetic MCs from the jump, and the gap in talent between him and the group’s other main vocalist, Ced-Gee, only became more pronounced with every release. The process of “going solo” was thus like shedding a vestigial appendage, and by the time Dr. Octagon dropped the rest of the crew were effectively footnotes. I don’t say this to be mean, because I honestly love those early records. But the truth is that nobody outside of the deepest crate digger was really hyped for a reunion album. It was a pleasant surprise, then, when lead single “Mechanism Nice (Born Twice)” hit so hard. Producer Moe Luv laces up a spacey boom-bap beat that calls back to the group’s early records without sounding dated. Keith asserts the group’s continued relevance, rapping “Dinosaur, I’m not dyin’ no more / We headlinin’ Dave Matthews tour,” which, okay sure. And even Cee-Gee drops some quality bars.

Alas, the album’s other tracks landed somewhere between forgettable and embarrassing—or roughly the same territory as the post-reunion Pixies’ albums. Still, it was a great opportunity for a new generation of listeners to explore “Ego Trippin’,” “Critical Beatdown,” and the group’s other classic bangers.

“Surgery [Featuring Motion Man]” – From Dr. Dooom 2 (2008)

Most fans had probably forgotten about Keith’s Dr. Dooom persona by the time he got around to recording a sequel album. Production was once again largely handled by KutMasta Kurt, but the creative partnership between the two was beginning to feel tired. There are no new ideas here (seven minutes in, Dooom kills Dr. Octagon again) and no tracks that even remotely approach past glories—save one exception: “Surgery,” which is an absolute gem thanks to Motion Man’s scene-stealing verses.

“The Force” – From Half Shadows (2013)

Even as Keith’s solo albums became increasingly repetitive, he was still inspiring innovation as a producer’s muse on outside projects. To wit, “The Force,” where he allows TOKiMONSTA to fire him deep into inner space on a psychotropic rocket. The L.A.-based beat maker was briefly signed to Flying Lotus’s label, Brainfeeder, and you can hear that influence in the track’s Djembe drums and kaleidoscopic layers of sounds. Keith, meanwhile, drops cosmic non-sequiturs from orbit—”Robotron coming up the turnpike”—before leading a call-and-response chant with the planet’s armed forces.

“Raw Scheisse” – From RetroMastas (2014)

Putting the rappers behind Dr. Octagonecologyst and Deltron 3030 on the same track seems like a surefire recipe for a banger, but most of their collaborations to date have felt awkward and forced—like when you try to introduce your work friends to your college friends at a house party. Thankfully we’ve got this track, where our heroes meet up abroad with German rapper Retrogott and finally get comfortable with one another. There’s Keith bashing other rappers’ Napoleon complexes and uneven hairlines. There’s Del rapping about searching for Zelda and bringing back the Triforce. And there’s Retrogott, sounding like the “real hip hop” your family’s foreign exchange student tried to force on you. Suddenly everyone is vibing out and all of your worlds have aligned.

“Twenty Fifty Three [Feat. Mr. Lif]” – From Time? Astonishing! (2015)

If Project Polaroid is Keith’s best project from the 2000s (and fact check: it is), then Time? Astonishing! is his most essential 2010s release. A lot of the credit goes to North Carolina producer L’Orange, whose noir-influenced production style—swing jazz samples, old radio broadcasts, traces of exotica—provides cinematic cohesion across tracks, and supports the album’s loose concept of Keith as a time traveler from the past seeking to escape the present. Keith is, of course, an old-hand at these improv-driven experiments, and he remains in character throughout, largely forgoing his familiar lyrical obsessions (save for a brief brag that “the hair off the penis drip like Keith’s Sweat”) to focus on the album’s retro-futurism theme.

He’s supported in this effort by a game cast of guests, including J-Live, Open Mike Eagle, and Mr. Lif on album highlight “Twenty Fifty Three.” Even MC Paul Barman (remember him?) pops up on “Suspended Animation” to dispense some nursery-rhyme-style witticisms (“My son asleep on my lap / Gives a chap a chance to eek out a rap”). The whole album breezes by in a pleasurable 33 minutes, making it a great entry point for old fans looking to engage with Keith’s more recent output.

“Bonneville [Featuring Mac Mall]” – From Feature Magnetic (2016)

“Super Hero [L’Orange Remix]” – From Super Hero (2016)

Keith’s relationship with Bay Area rap dates back to the mid-90s, specifically to “Record Haters,” the first track on E-40’s classic Hall of Game album, where 40 mentions reading an issue of now-defunct rap magazine 4080 with “Kool Keith […] on the front cover” and seeing a dismissive quote about him from AZ. The reference to Keith appears to be purely scene setting, but Keith took it as a compliment and shouted out “E-40, Mac Mall, C-Bo, and other rappers you don’t know” on “Plastic World.”

It wasn’t until 2016’s Feature Magnetic, though, that we got a proper Bay Area collaboration with the Mac Mall-supported “Bonneville.” This is the closest Keith has ever gotten to G-Funk, and his audacious brags (“Ten Cadillacs pull up in the festival / Women I send a jet to you / Fly my own planes like Wilson Pickett”) sound terrific over the track’s lolling, hypnotic groove, while Mac Mall delivers pure Vallejo vibes with a nimble, tongue-twisting verse.

As great as “Bonnevile” is, Feature Magnetic’s real draw for fans was “Super Hero,” which paired Keith with the equally gonzo MF DOOM. The two had sounded terrific on VV:2’s “Doper Skiller,” but hadn’t appeared together on an official release since. Both rappers bring their A-games here while building on the comic book theme, with DOOM going deep in his bag to reference Puck from Alpha Flight and Keith (naturally) riffing on “a place where superheroes meet up / the X-Men drinkin’ tea / watchin’ chicks with D cups.”

It’s a solid track that is unfortunately undercut by Keith’s self-produced beat, which plods along listlessly. Thankfully L’Orange rectifies this with a banger remix that so perfectly aligns with the bars you’d swear it was the original version.

“Sword In The Stone” – From Anything But Words (2016)

Anything But Words, the 2016 collaboration between Interpol vocalist Paul Banks and Wu-Tang impresario RZA, is an album that generated more features than spins, and there’s no need to revisit it here other than to note that (a) the Kool Keith-featuring “Sword in the Stone” is by far the best track on the LP and actually sounds like something that could have been on Bobby Digital in Stereo back in the day, and (b) a Judgment Night soundtrack-style project that paired Meet Me in the Bathroom-era bands with Okayplayer-approved acts from that same period (so like The Strokes & Dice Raw, Fischerspooner & Dead Prez, Har Mar Superstar & Rah Digga) is not the worst Kickstarter idea ever.

“Mars Attack” – From Anima Mysterium (2019)

South African rapper Yugen Blakrok followed her high-profile appearance on the Black Panther soundtrack with Anima Mysterium, an album that blends indigenous spirituality, psychedelic space vibes, and futuristic soundscapes in a fashion every bit as cinematic as the Marvel film. Keith is a perfect collaborator in this setting, and on “Mars Attacks” the two artists play out a Warhammer 40,000 campaign over producer Kanif the Jhatmaster’s trip-hop-esque beat.

“Ruff ‘n’ Rugged” – From Camera of Sound (2021)

“Ruff ‘n’ Rugged” is a collaboration with Scottish production duo and boom-bap revivalists Jazz Spastiks. It’s an interesting pairing, as Keith’s solo work in the 1990s was in some senses an “alternative” to this very New York sound, which he seemed to have outgrown by the time he decamped to Los Angeles and left Ultramagnetic MCs behind. He sounds fantastic here, though, with bursts of street-smart lyrics delivered in his distinctly rapid cadence.

“Extravagance” – From Keith’s Salon (2021)

Keith worked with yet another production duo, avant-house maestros Bruno Pronsato and Benjamin Jay (aka Benoit & Sergio), on 2021’s Keith’s Salon—the 39th full-length album of his career (according to Wikipedia’s sprawling discography page) and the best one he’s released this decade. There’s no high-concept or new alias here, it’s just Keith role-playing as himself and free-associating across timelines. “That’s me at the table for three / me, Beyoncé, and Jay-Z / they told me I’m the top skater in Skate Key,” he brags on “Yachts,” with Skate Key presumably being the long-shuttered Bronx skating rink he must have frequented in his youth.

Like Time? Astonishing!, this one feels like the producers swinging big to create an album that sounds every bit as fresh & forward-thinking as Dr. Octagonecologyst, Sex Style, and even Critical Beatdown did back in the day. And though this project never quite reaches those heights, tracks like “Extravagance” and “Bright Eyes” are top-shelf contributions to the Kool Keith pantheon.

“Kelly Had A Seizure” – From Orange is the New Black (2022)

Orange is the New Black, a collaboration between mysterious UK rapper Robert and producers Sonnyjim and The Purist, is one of 2022’s more intriguing releases thanks to its strange brew of freak folk, psychedelic rock, and druggy boom bap. Keith pops up on “Kelly Had a Seizure” like a clockwork elf during a bad trip, briefly restoring order to the universe while warming up “some hot soup and sh*t” for the aforementioned Kelly. It would be easy to get lost in a song like this, but Keith catches the vibe immediately and is completely at home.

How many rappers still sound as nimble at 50+ as they did in their 20s? How many artists, period, are still making music this innovative this far into their careers?

Related Posts

Ghost in the 404: This Month’s Best Electronic Music

The Alchemist Announces New Album ‘Haram’ With Armand Hammer

Behind the Beat: How Pete Rock & Nas Made Hip-Hop Perfection with “The World is Yours”

Pusha T Reveals Cover and Tracklist for ‘It’s Almost Dry’

“I Got Shit for the Ladies, Youngsters, Hustlers, and Doctors”: An Interview With WiFiGawd

Young Thug’s Trial is Getting Delayed