The Wild and Wonderful World of Tyler, The Creator

I Did It My Way
Tyler, The Creator lays claim to arguably the best hip-hop album of the year, and 2021’s not even done yet. Close to 15 years in hip-hop at his back and respect from peers and vets alike, the rap visionary has no limits on what he’ll do next.
Words: Georgette Cline
Images: Cam Hicks
Editor’s Note: This story originally appeared in the Fall 2021 issue of XXL Magazine, on stands in October 2021.

Tyler, The Creator loves to bring home the bacon. While he’s accustomed to racking up plenty of bluefaces thanks to six critically acclaimed albums, the 30-year-old rapper isn’t focused on the money-inspired idiom at the moment. He’s driving through Los Angeles’ residential streets in his “Green Goblin” Rolls-Royce Cullinan on an overcast afternoon in late August, fixated on his favorite real-deal bacon discovery at Whole Foods. “It’s called Dry Rubbed Black Forest,” he tells his passengers, including longtime friends Jasper and Lionel Boyce. Tyler describes the meat with a gleam of excitement in his eyes, like he just heard the perfect song for the very first time. “It look old. That shit is gorgeous.” He finds joy in the unconventional details of life, even down to what he’s eating.

Sir Baudelaire, the fresh, fly moniker Tyler adopts on his latest album, Call Me If You Get Lost, is also annoyed by slow drivers in front of him (“I wish you would drive, bitch”) and amused by a jogger to his right (“She ran like a fucking dork”) during the ride. Once Tyler arrives at his destination to grab a sandwich for lunch—hold the aioli or, as he jokingly warns Jasper, who grabs the food, “I’ma sock you in your dick”—The Creator proves to be swift with parallel parking. The car connoisseur owns two Rolls-Royces, two Lancia Deltas, a Fiat, BMW E30 and a McLaren. Tyler, dressed in a black ushanka hat, black Lacoste cardigan, blue Golf le Fleur slacks, loafers and a necklace full of pearls the size of gumballs, prides himself on being an excellent driver. He’s the type to throw his arm in front of a passenger when he does two quick U-turns while heading back to his Golf Wang office. A natural reaction he picked up from his mother he says. Yet, Tyler takes even more pride in his career. As he reflects on nearly 15 years in hip-hop while behind the wheel, the multiplatinum-selling artist owes his longevity in the game to three key things. “’Cause I’m good,” Tyler insists. “’Cause I care. And I didn’t start off at the top.”

He’s familiar with being at the top, though. Tyler, The Creator, born Tyler Okonma, started at the bottom in 2007, with his rap group Odd Future and the release of their first mixtape, The Odd Future Tape, a year later. They parlayed their exuberant, shock-rap energy into an empire that went beyond music, including the sketch comedy show Loiter Squad and OF merchandise decorated with Tyler-created pink doughnuts. Simultaneously, Tyler, like other Odd Future members, was branching out on his own. 2009’s Bastard tape kicked off his solo work. The Creator’s successful clothing brands Golf Wang and Golf le Fleur, a production company, sold-out tours, headlining music festivals and throwing his own, plus coveted partnerships like Converse followed.

The MC has solidified his place as a paramount raconteur at the top of the charts with his last two albums locking in No. 1 spots on the Billboard 200 chart: 2019’s Grammy Award-winning lovelorn opus Igor and Call Me If You Get Lost, his nod to rap’s mixtape era and arguably the best hip-hop album of 2021. Tyler translates the anomalous world of his albums to the stage and creates a weird reality in videos that have made him a vanguard on a steady rise. He peppers varying moods, ingenious puns and slick rhymes throughout his projects while evolving from a “they are them, we are us, kill them all” mentality to “a young, focused Black boy, oh, silly me.” The rhymer’s musicality is elevated through a lens of escapism and fearlessness, never taking himself too seriously and treating his voice like an instrument.

It took Tyler over 10 years to receive his first platinum record, 2019’s “Earfquake”— released that same year and now three-times platinum—but success is in the eye of the beholder. The Creator’s career is a red chart emoji—getting better with time. Everyone from 10-year-old kids to 50-year-old men, according to Tyler, are turning up to his music now. “I’m fucking great,” he says matter-of-factly of his life thus far. “I’m blessed.”

Long before Tyler was “talkin’ that fresh shit, I don’t need gum (No)/Cookie crumbs in the Rolls, never no weed crumbs (No),” on his CMIYGL track “Corso,” the Hawthorne, Calif. native, who doesn’t drink or smoke, was whetting his music appetite at age 4 with albums from singers and groups his mom played: Zhané, Faith Evans, Rachelle Ferrell and Brownstone. Usher’s My Way captivated him—Tyler still knows all the choreography to the title track’s visual. “‘One Day You’ll Be Mine’ is my favorite song on that album,” he tells. “I believe that’s track nine.” Tyler, who writes, composes and arranges his own music, directs his videos as alias Wolf Haley and produces for other artists like ScHoolboy Q (“Big Body” featuring Tha Dogg Pound), Westside Gunn (“Party Wit Pop Smoke” featuring Keisha Plum) and, most recently, Maxo Kream (“Big Persona”), can list off specific songs with their corresponding track numbers on albums past and present in seconds, like an eager kid naming every Pokémon character and their special abilities.

In a genre where rappers are often thrown into the music industry fire to chase a No. 1 with little comprehension of its history, his encyclopedic knowledge of music is respected. Tracks 14, “Love Won’t Wait” with Macy Gray, and 16, “Positivity,” from Black Eyed Peas’ first album, Behind the Front, mark the first songs he wrote raps to at 7. “I’m still learning genres but like, Damn, that’s jazz,” Tyler reminisces, identifying the composition of BEP’s tracks as a kid. “Then, they kick in and they’re rapping and I’m like, Wow, this is sick. And the drum patterns kinda skip and stuff and I’m like, This is sick. And then, Dr. Dre’s 2001 comes out. This is like, fourth quarter ’99, and I’m hearing this Eminem guy and I’m like, What is this? And it was this channel called The Box.” Tyler is clearly a student of the game.

Eminem, Lil Wayne, André 3000, Missy Elliott, Busta Rhymes, Pharrell Williams and Jay-Z are among the rhymers whose artistry has most influenced Tyler’s own. The latter two he also calls “real big homies.” “I’m one of the few who’s really listening and learned how to kind of run businesses since I was 17, because of [Jay-Z],” Tyler shares.

The polymath taught himself to play piano at 12, the same age his mom put him on to a valuable life skill. “On my 12th birthday, she was like, ‘You’re going to learn how to wash your own clothes,’” he says. She raised her rapping son on her own with the help of his grandmother due to Tyler’s absent dad. At 15, Tyler locked in his first jobs—FedEx and a Starbucks barista. Soon after, in 2007, he formed the now-defunct rap group Odd Future and the rest is history.

Christian Clancy, a 25-year music industry veteran who’s managed Tyler and OF along with his wife, Kelly, since 2010, through their 4 Strikes management company, first saw the then-novice artist through his “French" video that same year. The clip, showing teen Tyler rapping with a pitched-down voice while surrounded by Odd Future members Jasper, Taco, Left Brain and more, immediately grabbed Clancy’s attention. “Things were all very similar,” Clancy remembers of other artists out at the time. “Everyone had the same car, wore the same Air Force 1s, had the same Scarface poster in their MTV Cribs episode and whatever may be. And [Tyler] just kinda, it was kinda like here was this kid who was like, ‘Fuck all that and I’ma do me,’ and it felt rebellious but smart and kinda self-contained and kinda fearless. So, it was just an energy, you know? It felt like an energy of everything that I have been a fan on or worked with in my life.”

The former Interscope Records marketing executive has worked with Eminem, 50 Cent and The Game and found a mentor himself in Em’s longtime manager, Paul Rosenberg. The longevity of Clancy’s relationship with Tyler and its success is a byproduct of witnessing artist-manager duos like Em and Paul, and 50 and Fif’s former manager Chris Lighty maneuver the music industry trenches together. Tyler considers Clancy to be a father to him “100 percent.” A sentiment Clancy returns. “I owe that man my life,” Tyler conveys. “I’m forever in debt to him. He changed everything. He changed my life, my friends’ life.”

That transformation came at the right time. Around 16, Tyler’s mom went to Sacramento, so he lived with his grandmother in L.A. for a time. “When she left, I knew how to take care of myself,” Tyler maintains of the job that prepared him. “I knew how to save money. I knew money management. I think [my mom] knew that. That’s why she was like, ‘OK, you stayed with your grandma, you’re not going to do no dumb shit. You know how to save and stack and do that.’” But there were tribulations, which he never speaks on. “Mom was in the shelter when ‘Yonkers’ dropped, I don’t say it (I don’t say it)/When I got her out, that’s the moment I knew I made it (Yeah, yeah),” he raps on the CMIYGL cut “Massa.”

“Certain things I never wanted to talk about or glorify,” says Tyler, whose mom beamed proudly beside him onstage when he accepted the Grammy for Best Rap Album in 2020. “Just things like that. But yeah, that’s just something I never said. Man, like, I put out ‘Yonkers’ and my mom…just came back to L.A. and was like in this weird spot, and it’s like, [how I rap on ‘Massa’], ‘I don’t come from money, they deny it/Since I don’t mirror the stereotypical products of my environment.’ Then I say, ‘Eight figures…,’ that’s where that line goes and it’s like, man, that’s why I’m so blessed and grateful to have this stuff, ’cause I don’t come from that.”

The flex rap on CMIYGL is so abundant because Tyler can finally boast about his worldly possessions. A large assortment of vintage trunks included, which he positioned in place himself for his XXL shoot, photographed at a whimsical Beverly Hills home six days before this interview. Tyler won’t reveal the value of his Louis Vuitton, Gucci and Goyard collection, but it’s clearly a sign he’s made it following humble beginnings.

Operating without fear when he creates is also an emblem of that success. Tyler says and does what he wants with care. The rap doyen is an unexpected victor in hip-hop for those who live in a bubble or only pay attention to social media. DJ Khaled was witness to that when Tyler’s Igor bested Father of Asahd for the No. 1 spot on the Billboard 200 chart in 2019. The We The Best leader took subliminal jabs at Tyler on Instagram after that; Khaled boasted he makes albums “that you actually hear the songs.” Igor, an entire LP based on the story of a man who’s in love with another man who’s in a relationship with a woman, signified Khaled’s loss to an unconventional rapper in a time when the culture is embracing LGBTQ+ artists or related content more than ever. Fans have been cognizant of the dance Tyler does publicly with his own sexuality since his explicit same-sex lyrics on Bastard. The homophobic rhymes he once received backlash for are no longer part of his work. Instead, women—and loving them—are prevalent, but so are lyrics like “I’ve been kissing White boys since 2004,” which he rapped on “I Ain’t Got Time!,” off 2017’s Flower Boy. In Tyler’s world, he leaves “people to believe whatever the fuck they want” when it comes to his music and personal life. Privacy matters. Straight, gay, bisexual, fluid or other, he won’t answer. “I’m just living life, brother,” Tyler says.

Some traditional hip-hop heads may criticize Tyler’s choices to paint his nails or wear leopard print as his signature attire, yet this year, he finally completed Call Me If You Get Lost, the rap album he always wanted to construct. He collaborated with Gangsta Grillz creator DJ Drama to make that mixtape era palpable again on what he describes as his personal best work. Tapes like 50 Cent’s 50 Is Here, Lil Wayne’s Dedication 2, The Clipse’s We Got It 4 Cheap, among others, inspired the rapper. In 2022, Tyler could walk away with his second Grammy Award for Best Rap Album. After winning one in 2020, he’d follow OutKast, Kanye West and Kendrick Lamar, who also earned Best Rap Album Grammy wins then came back two years later to win another.

Tyler’s odd humor may elicit laughs, but he’s serious about his craft and taking risks to achieve his particular vision. “[Tyler’s] always willing to try something just to see if it works or doesn’t work,” says Lionel Boyce, who’s been friends with The Creator since they were in 12th grade drama class together. Now they are creative partners in their company, Bald Fade Productions, which has a first-look deal with Sony Pictures Entertainment. Loiter Squad and The Jellies! include some of their writing and acting credits. “There’s no limitations, you know, if you run an idea by him or you’re like, ‘Man, I wanna do this thing, but I can’t do it.’ He’s like, ‘Well, why not?’ He’s always saying, ‘Why not? Just do it, just try it. There’s really no real obstacle. You’re just limiting yourself instead of just going for it.’”

Jasper echoes those sentiments. The actor and writer, who will appear in Jackass Forever next year, has attended every Tyler show, according to The Creator himself. As DJ and hype man, Jasper witnessed almost 400,000 people at Tyler’s headlining set at Lollapalooza this year. “[Tyler] does what he wants and he doesn’t let nobody steer him the wrong way,” adds the Odd Future member, whom The Creator knew since age 16. “When he has his mind on something, he’s gonna get it.”

Clancy surprisingly has never witnessed apprehension in Tyler either. “He just handles things as they come to him in a very matter-of-fact way,” Clancy tells. “I don’t know if I’ve seen actual fear in him, which is crazy.”

Meanwhile, Kendrick Lamar keeps Tyler on his loafer-covered toes. Hearing K-Dot on Baby Keem’s track “Family Ties” ruined Tyler. “You know why it ruined me? Because it’s someone at that level still gunning,” The Creator says of his friend’s talent. “He’s trying new voices. He’s trying new shit. He’s still learning. You can tell he was off his phone for a few months.” He admits Kendrick is probably sick of him calling every two days about the verse, but it burned a fire in Tyler’s back to “just stay weird and stay tryin’.” Two thriving Tyler attributes.

He’ll apply both to the next chapter of his career. Tour starts next year and another album will come when he decides to drop it. “Maybe,” Tyler answers when probed if it’s already in the works. “I’m always working on music.” Right now, he’s looking ahead as Tyler, The Movie Director. He’s been at the helm of his own lauded music videos and brand commercials for over a decade, since “French,” so a full-length film makes sense. In 10 years, Wolf Haley hopes to have two or three movies he’s directed under his pearl Fleur belt. Think signature dark humor and weird surrealism, but cute.

Standing outside his office, Tyler, The Creator is a poster boy for exaltation because he’s never dimmed his light in the face of restrictions. He’s moonwalked in a wig around them or driven a boat through the grass right over them. “I live like it’s no rules and I’m OK with fuckin’ up,” he expresses. “I just brush my shoulders off and get back up.”

Go and brush your shoulders off.

Check out more from XXL magazine's Fall 2021 issue when it hits newsstands in October 2021.