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Tyler, The Creator & Earl Sweatshirt Are Finally Comfortable

In 2018, Earl Sweatshirt and Tyler, The Creator find themselves sitting in a long-stewing sense of self-awareness.
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This past Friday, I said goodbye to one of my best friends who is relocating from New Jersey to North Carolina. Before his family sprung the surprise move on him, another friend suggested we end 12 years of close-proximity friendship the way we’d ended so many nights before: by going to the movies. 

While our showing of Widows was slightly disappointing, the rest our night certainly wasn’t. The usual bits of geek current events and cinematic deconstruction gave way to a solemn drive back to my car. My departing friend and I shared a fist bump and I told him I loved him. He told me he’d see me online. The early morning air was cold but the warmth in my heart helped me back to my car as my two friends, one dead set on a traveling down a new life path, sped out of the theater parking lot. I’ll miss him, but I know he’ll be okay. C’est la vie.

Eight years earlier, in May 2010, Tyler Okonma said goodbye to his best friend Thebe Neruda Kgositsile. Okonma had taken Kgositsile under his wing after finding his music under the name Sly Tendencies on MySpace and convinced him to join up with a still-growing collective called Odd Future. Kgositsile—now going by Earl Sweatshirt—released his debut project Earl through the Odd Future Tumblr page to widespread acclaim, what was sure to be the first of many drops from the bleeding edge by the internet’s latest rap savant. The 16-year-old prodigy and his new big brother were poised to take over the world. Just two Black boys raising some hell. Of course, this was before Kgositsile’s unexpected trip to Samoa less than a month later.

Time’s arrow neither stops nor rewinds; it only ever moves forward, as do the priorities of preteens. Odd Future mania took over the world as Sweatshirt faced his demons in reform school. He returned to his friend eight months later, but their priorities were no longer the same. 2012 was the year of Sweatshirt’s homecoming show at the Hammerstein Ballroom in New York, and while the crowd and Odd Future as a whole were more than ready to welcome the prodigal son back, he was clearly in another place. Ironically, this show would end up serving as the nexus point for both Tyler, The Creator and Earl Sweatshirt, one that has led each artist down a long-stewing path of self-awareness. 

Sweatshirt, of course, took a dimly lit path. His first post-Samoa project Doris—named for his late grandmother who passed shortly after its release—draped his dense lyrical displays in the fog of post-fame anxiety and generational trauma. Lead single “Chum” was as personal a record as he’d ever made, a road map through his mixed feelings about his parents and his mentor slash best friend Tyler that ended with an admission that was shocking for a 19-year-old on the verge of stardom: “Been back a week and I already feel like calling it quits.”

That anxiety is only amplified on his 2015 follow-up I Don’t Like Shit, I Don’t Go Outside and bonus EP Solace, projects that simplified his message even further. The beats were darker and the rhymes were condensed and cutting, a firm look in the mirror after relapsing into drug addiction while on tour months prior. “People think being alone is a luxury, but it's crucial: Whatever you're not down with about yourself gets loud and in your face," he told Billboard in 2015. "It's about being OK with yourself, for better or worse. You can't really start living until you can live with yourself."

It’s a lesson he’s seemed to internalize on Some Rap Songs, his third studio album. The Earl of 2018 has mended his relationship with his mother Cheryl Harris and kicked his drug addiction, but was denied a heart-to-heart with his estranged South African poet father Keorapeste Kgositsile, who passed away suddenly this past January. Even still, he’s come to accept that. “Mama said she used to see my father in me / Said I was not offended,” he sighs in the middle of “Azucar,” a sunbaked song dedicated to the blessings that help him cope with life. He confides in friends from New York’s underground rap scene like MIKE and Sixpress, in the spirit of the late Mac Miller and in the Black women in his life over a shimmering, Dilla-esque orchestral loop courtesy of Navy Blue, aka Sage Elsesser.

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The concept of “imprecise words”—a recognition of his own lack of clarity—is a recurring theme, but Some Rap Songs fights for every inch of lucidity. We have the acceptance of depression (“Keep a noose hangin’ off my neck” from “Cold Summers”), being unable to predict the future (“Sittin’ on a star thinkin how I’m not a star” from “Veins”), and being robbed of the opportunity to show his father the peace offering that was “Playing Possum,” an audio collage of the elder Kgositsile and Harris reading a poem and a keynote speech, respectively, overlaid as if in call-and-response. Even Sweatshirt and company’s gratingly beautiful production finds comfort in the deliberately muddy loops of lo-fi hip-hop; Madlib by way of a warped radio cassette recorder.

The last two tracks on the album—the spacey distortion of “Peanut” and the sunny “Riot!”—zero in on the beauty at the center of the emotional hurricane, literally carrying Sweatshirt off of the album as the bright trumpet riffs sampled from his uncle Hugh Masekela reinforce the importance of taking this life a day at a time. Time is a sea with choppy waters, and Earl is both content and self-aware enough to be the wind in his own sails.

As for Tyler, The Creator, his path came with a bit more resistance. The Odd Future frontman continued to lean into the irreverence that Sweatshirt ran away from, creating a pastel-colored media empire and lashing out at anyone—parents, the LGBTQ+ community, the British and Australian governments—who objected to it. He had the clothes, the cars, and the money, but behind it all, he was lonely as fuck. His artistic vision began to meet his energy halfway on 2013’s Wolf, relishing more complex musical arrangements that cribbed as much from Hans Zimmer as they did from The Neptunes. It wasn’t until 2017’s Flower Boy that he found the words to say what he’d been feeling all along: he was a misguided shock jock hell-bent on pushing away a world he himself was afraid to publicly embrace. Flower Boy wasn’t an olive branch offered over past wrongs but a platform for him to speak his truth and reach an audience wider than his craziest OF dreams.

This could very well be what endeared Tyler to a character like the Grinch in 2018. The hellraiser who once couldn’t care less about anything family-friendly contributed two songs to Universal Studios’ The Grinch, including a remake of the iconic “You’re a Mean One, Mr. Grinch.” The jauntier raps of the original song “I Am the Grinch” draw a stronger line between artist and subject, the Grinch’s life of misplaced hatred and present stealing paralleling a certain young MC ready to watch the world burn. “You’re so problematic,” guest vocalist Fletcher Jones says, to which Tyler replies, “Yea, yea.” These two songs and the six-song EP Music Inspired by Illumination & Dr. Seuss’ The Grinch are logical next steps in the journey started by Flower Boy last year. 

At this point, Tyler isn’t simply following in mentor Pharrell Williams’ footsteps, he’s leaning into them with a crooked smile. He’s truly becoming hip-hop’s Willy Wonka.

I can’t imagine any of this happening if Earl and Tyler hadn’t gone their separate ways in 2012. Even as best friends who both lacked father figures and who both hid exceptional musical talent behind a DIY punk veneer, they’ve grown more on their own over the course of six years than they probably would have if they were still shouting “Kill People, Burn Shit, Fuck School” around the world. 

I trust that my friend is making due down in North Carolina. Even if I’ll always wonder what EarlWolf might’ve sounded like, Earl Sweatshirt and Tyler, The Creator are their own people in 2018. Just two Black boys growing up. We ain’t got time for much else.


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