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Photo via Liam Walsh

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Harley Geffner knows that every job will eventually be automated until just 3 remain: baller, shot-caller, 20 inch blades on the impala.


Drippin So Pretty’s music conjures up images of gun-toting paranoia, death’s creeping presence, and drug-induced sorrow, but the 27-year-old rapper lights up the room the moment he walks in. He has a magnetic personality, cracking jokes and broaching sensitive subjects with equal parts clarity and sincerity.

Originally raised on the coast of San Diego county, Drippin So Pretty made the move to Los Angeles at the age of 22 with the help of his girlfriend’s mother after a string of teenage arrests and addiction caught up with him. Already acquainted with GothBoiClique’s Cold Hart via Instagram, he quickly landed on his feet and established friendships with the likes of Lil Tracy, Horse Head, and Nedarb, all powerhouses of the GBC movement. “When I moved up here I was super stoked that I was linked up with dudes who already had some shit going up here and felt a part of — still not in their circle — but a part of something,” he remembers.

While he was finding his footing, the foundations of Drippin So Pretty’s signature sound began to take shape with songs like 2017’s startlingly honest “Last Shot ‘Heroin.’” The lyricism was deeply personal, and perfectly matched the emotions of the soft and fuzzy guitar-string production. “I kind of saw how open I can be with my past,” he recalls. “I mean that song’s pretty fucking gnarly. That’s kind of when I started gravitating more toward the guitar shit.” His ear for melodies and their emotive inflections was immediately apparent as well — a talent that he sourced from two of hip-hop’s most influential personas: Chief Keef and Soulja Boy. He reflects, “I think that even being 18 and listening to Chief Keef and stuff, like he’s melodic, like his autotune stuff is very melodic … and listening to even, like, old Soulja Boy with autotune, I just love that shit. I think I fucking learned more singing listening to that kind of stuff than actual singers, you know?”

After releasing an array of singles and mixtapes, Drippin So Pretty entered 2019 with the unveiling of True Love, True Pain and Die For You. These projects showcased his voice’s evolving ability to blend glistening meditations and bold boasts. He subsequently embarked on a European tour around the debut of Die For You with close friend and collaborator Brennan Savage, but true to his prolific creative process, he was already thinking ahead. “It was a really cool experience, cool to perform in front of people and shit, but I don’t know … I always think my new music is my best music, so looking back at it, I’m like, ‘Fuck bro.’ I wish I was over there doing Back From Hell and Rest In Peace, like fuck, you know?”

In fact, 2020’s Back From Hell would begin to take shape on the tour. He recalls, “I started off writing Back From Hell actually when I was in the van driving in Switzerland when I was on tour with Brennan. I really liked that skress beat [on the title track] and I was laying some of the shit down with Lotus’ little brother. He was tracking at his house and then I just ended up finishing it in my room and recording it with Prettyheartbreak, but I don’t know, those beats are just fucking hard.” He’s quick to emphasize the spontaneity of the project coming together on the road as he affirms, “Sometimes bro, that shit just happens, like some crazy shit will just pop up in your head or to a beat and you like, just spazz, I don’t know. It’s cool when that kind of shit happens because … I don’t just be making up bars in my head and thinking of raps and stuff all the time, so I think it’s kind of cool when those creative things happen.”

That release would give way to 2021’s Rest In Peace, the majority of which was produced by the increasingly present thislandis. The intuitive chemistry between the two artists was the result of a slow and steady evolution, from trading sessions circa Die For You to learning each other’s strengths and hitting their creative stride as a dynamic duo. There’s also a sticking point in their process that applies to the entirety of Drippin So Pretty’s workflow — he needs genuine dialogue to stimulate the creative process, avoid stagnancy that online work is prone to exacerbate, and ultimately find exactly what he’s looking for. “You can conversate, you have that communication with them, so I have that with landis, I have that with skress, with taylor morgan — someone who I’m working with — you know Charlie [Shuffler], 4evr too … a couple other people too, I think. I just build that communication with them,” he explains.

Equally central to his artistic beliefs is the idea of not forcing collaborations, as the album’s only features are from Lil Tracy and Brennan Savage. He states, “Those are the dudes who are just my friends, you know? I’ve never reached out to a bigger artist to give me more exposure or some shit, I just feel unorganic or whatever … I just don’t care about that shit, I just want to have fun and do shit with my friends.” He goes on to ponder the point he’s arrived at with unflinching honesty, a characteristic that becomes essential to his identity as he remarks, “I know I’m not going to be the biggest artist in the world, so I’m just grateful for what I have, ‘cause it’s like, amazing that I would never think — even before I started making music — that I could do anything like this [laughs] or be alive this long to see any kind of success.” It’s a morbid reflection at first glance, but there’s a keen sense of survivor’s humor to be found after one makes it through hell and back.

Drippin So Pretty’s gratitude for life is indeed apparent as he balances unflinching examinations of agony through his music with genuine joy in his day to day moments. “I just like fucking joking with my friends on the phone and shit, just fucking calling homies that aren’t in Cali,” he says. “My music can come off as dark and stuff, but … I do like to be joyful and joke around, that’s the only thing that keeps me going.” He adds, “It’s kind of funny, when I first started doing this shit I’d go around and I’m like, ‘What the fuck?’ Some people really try hard to live up to their image and I’m like, ’Bro.’ That’s the funniest shit to me [laughs], ‘cause I’m like, ‘Bro, what are you, an Instagram photo in person [laughs]?’”

He seems to have a knack for helping people reveal the true selves they’ve been conditioned to hide in their social interactions. Positioned within an artistic world that seemingly necessitates artificial personas, he breaks down that wall and incisively approaches the real. “I feel like everyone has different versions of them and shit, it’s just kind of funny when motherfuckers be like [laughs] bringing their image into everything. Honestly dude, I feel like I’m really good at bringing that out of people, like that, ‘Hey dude, it’s a safe place to be yourself here, you don’t have to be the artist version of you.’ I feel like I’ve always been good at that, kind of being that light.”

Alongside his appreciation for life comes a contemplative perspective on personal attributes like sobriety, both in the visceral pain of past usage and his present approach to maintaining abstinence. He admits, “It’s not hard to not pick up a drink or drug now, but definitely the thought has never gone away, you know? Yesterday I was in kind of a slump, and those thoughts were manifesting themselves in my head and I fucking was going down the rabbithole.” He’s conscious of when he’s recalling old mental habits, though, as his collective experiences provide him with a more immediate ability to ID outdated thought patterns. He explains, “I’ve been doing this for so long that I can tell when I’m really falling off the edge or playing with the idea in my head. So it’s not easy dude … It’s always better as long as I’m not on fucking drugs and alcohol, but it is hard … It’s not hard, but I’m constantly reminded that it’s there, you know what I mean?” That reminder is at times uncomfortable, but it’s one that can keep someone struggling with drugs and alcohol honest in difficult daily moments, preventing the return to a worn-out road with nothing but agony at its end.

Drippin So Pretty also emphasizes the need to maintain a certain level of stability in his social interactions so that he remains grounded — at this point, being extensively around drugs and alcohol has long lost its luster. It’s a situation that everyone in recovery faces, but especially those in a cannibalistic industry that’s normalized substance use and abuse to the point of a collective numbness. “I can’t fucking be around people getting loaded all the time,” he explains. “Like I can do it a little bit, then fucking, it’s exhausting for me because my mind is racing the whole time and it’s like, I don’t obsess over drugs and alcohol when I’m by myself, but you know when I’m around it long enough, it’s like I start to get that obsessive thinking, and it’s not like I’m going to go do it, but it’s just exhausting … Even just your brain feeding into that and having those memories of a good time, and it’s like, ‘Bro, shit’s fried.’ I just like that analogy: ‘If you’re in the barbershop long enough, you’re going to get your haircut.’” It’s an astute comparison that highlights just how much proximity to using is tolerable before it necessitates an ejection from the given situation, like a pilot parachuting toward safety.

He goes on to acknowledge that while there’s significant space between him and his last drink or drug, some of the deep-seated pain from lifetimes worth of suffering remains. He ponders, “I’ve withdrawn from heroin and suboxone probably over a few hundred times, you know? So it’s like, that … kind of like paints the picture of how much agony I’ve put my mind and body through, and how torturous — self-torture — I did to myself living that kind of lifestyle for so many years, and then doing really good and making everyone proud, and then not … I just feel like after having a significant amount of time off that shit and still fucking toying with the idea in my head, I just feel broken … Why is this shit still coming to my mind after I’ve gotten so good?”

Fortunately, he’s found solace in a network of supportive people. That web of numbers to call and faces to rely on treats an inherently antisocial condition, one that thrives on isolation before eventually retreading into a singularity of misery. Drippin So Pretty is one of those who has been fortunate enough to find this gift and put it to good use. “I’m fucking stoked that I have so many different tools now,” he explains. “Like when you actually do this shit, it’s more of a relief that I’ve been able to pick up the phone when I’m in this kind of slump, like that’s a miracle in a sense, you know? Just being able to pick up the phone even though it’s heavy.”

This heaviness also infiltrates Drippin So Pretty’s life through the recurrence of death. Ranging from the loss of his father to countless childhood friends, he notes that he seems to lose at least one close person a year. He’s candid about the topic throughout his lyrics, most recently on the standalone single “Ride or Die” where he sincerely confesses, “I ain’t been the same since my brother died, I ain’t been the same since my father died.”

To him, music and death are intrinsically tied together as it provides a level of catharsis that’s otherwise unreachable. “I feel like death and music go [hand in hand] … For me, I can’t just cry thinking about my dad dying, but me and my mom made this video for my dad, this memorial video … When we watched it together — they hadn’t even been together for 10 years — but when we watched it together, we were fucking crying because the song fucking … these violins started playing in the song and then it’s like a picture of him holding me in the emergency room smiling.” He confesses, “I watched that yesterday and I cried, you know? It’s like, I think that I don’t cry to my own music, but you know, maybe if someone’s thinking about some shit or they’ve lost a parent or they lost really close friends and they’re listening to my shit, maybe that’ll pull their heart strings or whatever.”

As for why the topic tends to appear throughout Drippin So Pretty’s music and the subsequent release it offers, he’s physically surrounded by reminders of his departed family and friends. He notes, “I literally have pictures of my friends that are passed and my dad in my room so it’s like when you’re in that environment, you’re just looking at shit … That’s what’s inspiring it I guess, or it’s me letting that shit out, you know? I’m grateful that I have that outlet, because I remember … there was this guy who was like, ‘I’ve stayed sober through both of my parents’ deaths and I never would’ve thought that I would do that.’ And I always thought that was a trip, ‘cause you know, addicts always look for those excuses.” It’s a blessing that he’s emerged from some of his own losses safe and substance free, avoiding the old outlet that many succumb to on a daily basis, instead committing himself to experiencing these painful passages in full.

His music has also become imbued with a fascination about life after death as he wonders what lies beyond. It’s not a morose reflection as much as it is a curiosity, one that’s natural for someone whose life has been interspersed with repeated tragedy. He explains, “I’ve been so fixated on what happens after we die, you know what I mean? … I never feel like my shit’s grim, you know? I feel like when I’m singing about that shit, it comes from that kind of place … it comes from, ‘What the fuck happens?’ You know? Is it nothing or what?”

He continues to detail some personal beliefs he’s been toying with, one where the potential for an energetic afterlife begins to take shape once our physical selves have moved on. “I’d like to believe that our subconscious goes somewhere else, you know? And that we get to be ourselves but somewhere else or something like that, you know? Because I just feel like energy is such a weird thing … Your energy can make an impression on someone and that’s how it is forever,” he says.

His tone turns bittersweet as he touches on the loss of a specific friend, while acknowledging the lifelong impression he left. There’s a grey area not exclusive to one emotion or the other as gratitude and pain are both present in his recollection, a combination that’s all too familiar when it comes to those taken away by substances. He remembers, “My friend Marlon that died, like this dude was the funniest person I know, and all of his humor made an impression on me since we were in elementary school … and so I feel like … goddamn, this fool died in such a fucking wack way ‘cause of drugs, you know? And I’m like, ‘Damn.’ This whole dude’s energy literally helped shape me into who I am today.”

Drippin So Pretty also touches on the impression his father left with a considerable level of vulnerability for such a close parting. He explains, “My dad was a really, really funny person. He enjoyed making people laugh and bringing up funny-ass stories and shit, and that’s how I am, you know? And I guess I never really thought about that until they were gone, you know? And I see it more clearly … I don’t like saying weird cliche things like, ‘Oh you’re going to live through us,’ but that’s kind of what that is I guess in a sense … I don’t fucking know, maybe we’re broken up into a million pieces and live through our fucking people or some shit.”

Alongside his people, Drippin So Pretty is hard at work on his next album, Betrayed, a project defined by artistic exploration with the potential for more experimental production as he branches out into new stylistic territory. He says, “I’ve always fucked with nostalgic techno shit, with girls singing on it and stuff, you know? … You just know shit’s transforming into more EDM shit so it’s like, ‘Okay cool.’ Someone making beats like that sends it to me and I’m like, ‘Okay, I can fuck with this,’ you know? But then I like doing it with someone like thislandis where I can add guitar on top of it and … make it my own little thing.” Even while expanding, Drippin So Pretty continues to champion his penchant for close collaborators, and most importantly, friends. With production from names like skress, taylor morgan, and 4evr, he also hopes to bring innovative associates like Nascar Aloe and Black Kray into the fold.

While each of his full-lengths is distinct and offers a time capsule of his creative headspace at that given moment, he’s aware that some of his fans are hoping for some evident shifts on Betrayed. He confirms, “There’s going to be different songs on there. Even though I feel like each album is different from each other in a sense, but I sometimes do look at comments and people are like, ‘Alright, this sounds like the same stuff,’ but then there’s hella people defending that and being like, ‘No, it’s the same fucking producer, they’re like Kobe and Shaq,’ you know? Definitely there’s going to be different types of swag on it, you know? Different beats, you know? Alright, I listened to those guys, whatever. I took into consideration [laughs]. I folded.”

There may be rapidly expanding attention (and opinions in the comment sections) as his spotlight continues to grow, but Drippin So Pretty recognizes the utmost importance of a sustained connection with his sobriety and spirituality. He pushes forward as a reflection of those still struggling and for those who didn’t make it this far, some of whose pictures are still on display in his room, never to be forgotten. It’s a testament to his willingness to change that he’s not only alive and sober, but creatively thriving with his best music now under way. A story of resilience forged from despair.

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