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Earl Sweatshirt’s Ode to Evolution

How the rapper embraces healing through honesty and self-awareness on ‘SICK!’

On February 16, 2023
Photo by Ryosuke Tanzawa

Earl Sweatshirt first emerged with Odd Future, the Los Angeles-based rap crew with dark beats and irreverent humor that spoke to the souls of maladjusted teens. Featuring would-be superstars Frank Ocean, Syd and Tyler, The Creator, Earl stood out largely because he wasn’t around. In 2010, right as Odd Future became popular, his mother learned of his music and drug use and shipped him to a boarding school in Samoa. His being out of sight made him a cult figure; messages of “FREE EARL” arose across the internet, which only heightened the pressure on him to be special. He wasn’t prepared for it. As he told me for an Entertainment Weekly profile, “Not only was I young, but I also missed the natural ascension and information that you pick up on the way up.” There wasn’t a road to greatness for Earl. He didn’t have to work out his material at open mics and clamor for notoriety. By the time he got back to L.A. a year later, he was already a superstar, but didn’t have the maturity to handle it. He had to learn on the fly, in public, with hoards of fans studying his every move.

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Born Thebe Kgositsile, the rapper grew up with a mother (Cheryl Harris) who taught law at the University of California, Los Angeles, and a father of South African descent (Keorapetse Kgositsile) who worked as a poet, activist and journalist. In 2019, he told Pitchfork that his childhood was “oppressive.” His mom, a writer, would make him scribble essays to properly explain his stance whenever he wanted something. Earl started rapping in the seventh grade under the name Sly Tendencies, releasing his debut mixtape Kitchen Cutlery on MySpace. In 2010, he put out his second mixtape, Earl, as an official member of Odd Future. Though the tape, with all its dark textures and gay slurs, was well-received upon its release, it hasn’t held up in the modern era of social reckoning. Earl himself has kept the project at arm’s length, writing it off as outrage from an angry teen.    

In 2012, Harris told the New York Times that her decision to send Earl away wasn’t solely about his music. “He was really very clearly going through a rough patch emotionally,” she said. It was “very evident that he was struggling.” Reportedly, he was smoking weed excessively and got caught cheating in school. At Coral Reef Academy in Samoa, Earl still got in some trouble for sneaking time on the internet to check in on his other life in L.A. Odd Future had started blowing up in a big way; he wanted to see just how famous he and his friends were becoming. In Samoa, the Times reported, Earl spoke with therapists, swam with whales and earned a scuba diving license. Though he wrote rhymes there, the idea was to disconnect and go home as a new person. His mother would send him articles about Odd Future’s success, along with a birthday card that Tyler delivered to his house. He soon went back home, then back to New Roads School in Santa Monica, to earn his diploma. The then-18-year-old resumed rapping with Odd Future, while reconciling his relationship with different group members. He came back re-energized and ready to take his career to the next level. 

Earl leans into that era on SICK!, his fourth studio album. “Came home end of 2011 … Ain’t know where none of this shit was headed,” he raps on “Titanic,” a Black Noi$e-produced cut with bouncy electronic drums and drifting cosmic synths. Then on “2010,” SICK!’s first single, Earl recalls his flaws from a decade ago: “Left the crib, smacked, no sheath on the sword / Made it by the skin of my teeth, thank God.” A few years ago, he wouldn’t have been so self-aware. But SICK! reveals a new Earl Sweatshirt, an almost-30-something father with renewed personal and professional purpose, who had to correct detrimental behavior for the sake of his young son. By Earl’s own admission, just two years ago, he struggled with a drinking problem that hindered his relationships. “I’m used to being real low maintenance, out of the way,” he further told me. “I can’t do that shit no more. Because there is nothing that will time travel you like alcohol.” In turn, Earl sounds clear-headed on SICK!; the groggy vocal tenor that inspired a generation of rappers persists, but the music is pared back for easier comprehension. Compared with 2018’s Some Rap Songs and 2019’s Feet of ClaySICK! paints a clear portrait of Earl — the good-natured protagonist trying to make sense of this masked-up pandemic world.

In a way, SICK! is a COVID record. The cover art depicts a framed mold of Earl wearing a mask over his mouth alongside two pills, some sage and a bulb of garlic. Recorded during lockdown as the virus took hold globally, it’s actually the second album he recorded in the wake of Feet of Clay. He had been working on a project called The People Could Fly — named after the Virginia Hamilton book his mother used to read with him as a child — but ended up scrapping most of it after people couldn’t travel due to the pandemic. SICK! not only speaks to people struggling to fathom a mysterious illness, it’s also about Earl’s own tribulations. Deliberately, the title track is meant to feel claustrophobic, like Earl recorded it in a small room with the walls caving in. “Something gotta give,” he deadpans. “Can’t go outside no mo’ ’cause n---as sick.” Isolation isn’t new to Earl, though: On his second album, 2015’s I Don’t Like Shit, I Don’t Go Outside, his solitude was fueled by the death of his grandmother. On Some Rap Songs, the ghostly presence of his dad and his uncle, the famed South African trumpeter Hugh Masekela, shadowed the dark corners of the album’s patchwork jazz, funk and soul. There, Earl has said, he wanted to honor his dad by being efficient with the written word. “You’re supposed to call a duck a duck,” he told me. “That’s what poetry has always been. Say what it is, tell the truth, move on.” 

Musically, SICK! splits the difference between the dense sonic layers of Some Rap Songs and Feet of Clay (both of which inspired debate about the perplexity of Earl’s recent music), and I Don’t Like Shit… and 2013’s Doris (which sounded closest to the initial Odd Future releases). SICK! represents a slight return to his older form in an attempt to make something more palatable. There are songs like “Old Friend,” “Lye,” “Fire in the Hole” and “Tabula Rasa” (the latter featuring the noted rap duo Armand Hammer), which deploy the kind of breezy funk and soul he’s preferred in recent years. In particular, the sauntering blues loop in “Tabula Rasa” feels equally active and withdrawn, the perfect sound for the rappers’ lyrical dexterity. Then there’s the song “Lobby.” Over big 808 drums, Earl spits one-liners about the burden of reconciling history: “I’m 26 / Felonious past / Rolling with the pack … Head hard, I’m stubborn as shit.” These lines illustrate his intersection between person and artist, and drive to the heart of what SICK! represents. Where I Don’t Like Shit and Some Rap Songs were steeped solely in despair, this album finds him taking stock of those feelings as a way to move forward. It’s the kind of maturity we all strive for the closer we get to 30, when late-night clubbing makes less and less sense, and the urge to atone prevails. Suddenly, the sins of yesteryear come rushing to the fore, repositioned as teachable moments. But you can’t reach a breakthrough without acknowledging your shortcomings, and SICK! is full of confessional rhymes intended as self-therapy. For 24 minutes, he pivots between darkness and light, crafting his most mature album yet. 

Earl could fill his albums with guest features from so-called A-listers if he wanted. But he’s gone the opposite way, rapping alongside elite — albeit lesser-known — talent like MIKE, Liv.e, Navy Blue and Quelle Chris; names with the same skills as industry faves, just not the same marketing budget. This creative shift came around 2016; while living in Brooklyn, he took a liking to MIKE’s music and purchased his album longest day, shortest night for $45 on Bandcamp. They became friends; by summer 2017, they spent time listening to music at Navy Blue’s house. Then he started taking in other work from that orbit — namely the experimental jazz collective Standing on the Corner and its album Red Burns — and asked bandleader Gio Escobar to contribute new sounds for Some Rap Songs. The new music rankled fans who craved more digestible work, not the muffled loops he opted for. But Earl wasn’t concerned with how he would be perceived. As he told Pitchfork in 2019, he wanted to get back to the art of making music. Some also said he was following a new trend and not establishing his own. But you don’t get rappers like MIKE and Navy Blue without the path that Earl forged all those years ago, which made it OK for lyricists to rhyme conversationally in their natural speaking voices. And just because Earl is a superstar doesn’t mean he can’t learn from like-minded artists. That he still sees himself as underrated is part of his superpower. “I think the important thing is community,” he once told me. “All these people have been creative siblings with me at one point or another.”

What we hear on SICK! is the most realized version of Earl to date: a man with the same wandering spirit as before, but with a newfound command of his celebrity. This Earl is far more serene and grounded in who he really is. You feel his curiosity when speaking with him; his thoughts tend to land broadly and touch on everything from African literature to spiritual jazz and ’90s hip-hop before centering on himself. When asked to unpack his own narrative, he tends to speak in terms of we and not I, leaning on the group aesthetic to explain his own rise. The emphasis isn’t surprising, given Earl’s recent love of fellowship, but for an artist who made his name as a loner, his optimism is refreshing to hear. For an album born out of seclusion, SICK! is a moving ode to evolution. As always, Earl is a testament to the healing powers of honesty and self-awareness.

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Marcus J. Moore

Marcus J. Moore is a New York-based music journalist who’s covered jazz, soul and hip-hop at The New York Times, The Washington Post, NPR, The Nation, Entertainment Weekly, Rolling Stone, Billboard, Pitchfork and elsewhere. From 2016 to 2018, he worked as a senior editor at Bandcamp Daily, where he gave an editorial voice to rising indie musicians. His first book, The Butterfly Effect: How Kendrick Lamar Ignited the Soul of Black America, was published via Atria Books (an imprint of Simon & Schuster) and detailed the Pulitzer Prize-winning rapper’s rise to superstardom.

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