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Slept On: A Series, Part Three: Earl Sweatshirt, by Jason Meggyesy

From the 2000s to the 2010s, the state of hip-hop underwent a transition. Gone were the days of Kanye West’s upbeat, heartwarming tracks about his mama opting for a more avant-garde approach to his music production. No longer was Drake an up-and-comer in the game. Rather, the Toronto MC had solidified himself as a star primed to take over in the years to come. What the rap community lacked was youthful breath, someone—or someones—to personify kids’ curiosity and angst at the time.


Insert Odd Future. This Californian collective was young, loud, and in your face. The skate-group-turned-rap-group-turned-brand embraced character and individuality; no two members were the same, but they all worked in tandem.


As the group gained popularity, Odd Future chose to bring different members into the fold. Within the new additions to the roster, a young rapper with a prominent forehead and large lips rose to the top and eventually helped elevate Odd Future’s pink donut logo to another level of international acclaim.


In the final installment of Slept On: A Series, we’ll examine the fascinating career of Thebe Kgositsile, better known as Earl Sweatshirt, and how his rise and self-imposed fall brought balance to the rap game.


Thebe found himself immersed in academics from a young age. Son of renowned South African poet Keorapetse Kgositsile and UCLA law professor Cheryl Harris, Thebe grew up around forward-thinking ideologies and intellectual discourse. Despite his educational upbringing, a young Thebe possessed a mischievous nature and found himself in trouble often. At around age eight, his parents split up, and the trouble continued. On the track Chum, the listener is able to hear how the departure of his father influenced the man Thebe would grow to become.


As a teen in high school, Thebe developed a passion for music and began to produce music under the stage name Sly Tendencies. During the Sly Tendencies era, the artist uploaded his pseudo-mixtape Kitchen Cutlery to MySpace in 2009. Although the mixtape was never finished, it caught the attention of many, including Tyler the Creator. Soon after the release of his “project,” Tyler would reach out to Earl, ultimately ending in the teenage rapper joining Odd Future.


At this point, Thebe chose to drop the moniker Sly Tendencies and swap it out for Earl Sweatshirt, a name chosen based on its comedic tone. After adopting a new persona, Earl was eager to get to work and produce new music.


In 2010, Earl worked closely with his mentor Tyler to construct his debut mixtape Earl. The 10-song project acted as the 16-year-old’s first statement to the game and was met with immediate acclaim. In 25 minutes, Earl mirrors his mentor’s early work with explicit and dark lyrics (Twitter would cancel his lyrics if they came out in 2021) while adding his melancholy flow to the staticky, barebones instrumentals displaying control over the chaos he created.


Earl emerged as the perfect running mate for Tyler and the Odd Future brand. Everything the pink donut rappers produced was a success. The eclectic group of counter-culture youths found themselves dabbling in TV shows, t-shirt collaborations, and music festivals—nothing was off-limits.


The good times would soon fade, however. Amid his successes, Earl’s mother became concerned about her son’s well-being and chose to relocate the budding rap star to a boarding school in Samoa for at-risk youths. During the stint on the island, as Earl often refers to it in his lyrics, Odd Future united around the group’s young star, boosting his stardom in the process. Members started the #FreeEarl campaign, a rallying cry they’d use every chance they got to keep Earl’s name in the forefront of people’s minds.


After a year and a half away, admirers welcomed Earl home with open arms. But the mischievous, playful lyricist had changed into a more serious and cynical wordsmith.


Earl put this new, mature persona to work in his 2013 debut album Doris. He spits nihilistic bars about his inner struggles and his anxieties with fame. This theme is prevalent in songs like Burgundy and Whoa, among other tracks.


Soon after Doris, Odd Future ultimately disbanded after disagreements among several members arose and other members’ careers began to move in new creative directions. Earl, too, feverishly tried to distance himself from the persona he had created as a 16-year-old, even condemning the glorification that he received earlier in his career.


Following the Odd Future break up, Earl faded away from the spotlight, choosing to disassociate from the world of fame. During his absence, Earl continued to write lyrics and prime himself for a return, if you could call it that.


After 2015, Earl released three different projects over four years. The first tape titled I Don’t Like Shit, I Don’t Go Outside, a project where Earl continued to spar with his inner demons continued to speak on the inner demons that Earl was battling with. Some Rap Songs (2018) and Feet of Clay (2019) were two projects where Earl pushed the envelope with his production style and captured the listener in a messy soundscape.


These days, Earl appears in public on occasion but keeps his time in the light brief. At only 25, the former Odd Future rapper is now a veteran of the game. As currently one of the most conscious and concise artists, Earl is a stark contrast to the flashy, repetitive rap stars who tend to rise to the top. A self-described “old-ass young person,” Earl offers a different perspective to rap. Earl provides much-needed brevity and awareness in his raps during a period crowded with bloated overzealous discourse consumed by streams and likes.


And with that ends Slept On: A Series. I hope by now you have come to appreciate what each of these artists have done for modern rap music. I hope you have enjoyed this series and continue to listen to tracks from your favorite slept-on artists. Till next time.

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