Tyler Gregory Okonma won the red carpet at this year’s Grammys — where his fifth and most recent studio album Flower Boy was nominated for Best Rap Album — donning a mixture of high fashion (a Louis Vuitton scarf) and his own fashion (custom Chuck Taylor High-Tops, a collaboration between Le Fleur and Converse), also rocking a baby blue Supreme coat, a traditional Russian ushanka hat, a cheetah print dye job, and accent stained teeth.

Both the peerless look and his institutional recognition represent a dramatic sea change in Tyler, The Creator’s reputation over the last decade since he first landed on the public radar swearing and screaming that he’s “a fuckin’ walkin’ paradox.” At present, Tyler is instead something of a polymath; his various cultural roles include that of a fashion designer, television tycoon, festival producer, budding filmmaker, and most recently, a symbol of hip-hop’s shift in focus towards artists breaking long-upheld boundaries of sexuality and gender identity. It’s a remarkable point for Tyler to reach from a career that began in the shadow of another audacious rapper who never made it that far in his own artistic evolution.

Tyler’s early adoption of Eminem’s ethos may have been as rooted in generational circumstance as personal connection. If you came into adolescence around the turn of the century, there were few artists as strikingly appealing as Eminem. There were few striking artists, period. During his incessant reign at the dawn of the new century, Ja Rule and Nelly were some of the most popular rappers in the country, Nickelback ruined karaoke forever with “How You Remind Me,” and American Idol had just launched the beginning of an unyielding experiment in populist star-breeding. The impression teenagers in the early 2000s had of their predecessors in the ’90s was that of counterculture basement-dwellers making their own rules and launching Nirvana ahead of Michael Jackson on the top of the Billboard charts. And what did our generation have? Boy bands? Mall-pop? Times were dim, and true to his word, pop culture would have felt empty without Em.

Of course, Marshall Mathers was always greeted as an unwelcome insurgent by much of the rest of mainstream America. He defied conventions at a time when most of us still believed in them. His voice — biting, nasal, spouting rhymes as outlandish as they were dextrous — already sounded out of place on radio waves defined by an adherence to glossy reinterpretations of standard musical forms. So instead of compromising to the middle, he simply moved everyone’s attention to where he was standing.

Along the way he infiltrated the consciousness of the country’s youth, before quickly taking over globally, and was cited as the cause of any number of cultural crises as such. But his influence on society was so vast as to make it unclear whether you could ever draw a direct line between his profanity-drenched provocation and anyone’s real-life actions. Blaming Eminem’s music for the misdeeds of bad seeds was like blaming gravity for avalanches: everyone is feeling its force at all times, so something else must have upset the equilibrium.

Accordingly, Eminem’s venture to turn unwarranted controversy into a game show for America’s most impressionable did not give birth to Odd Future. The antics of the notoriously incendiary Los Angeles hip-hop collective had greater precedent in the region’s history of confrontational rap music, as well as punk-rock and skate-culture, and Eminem never had a trademark on unprompted shock tactics anyway.

That said, he almost certainly had a hand in Odd Future’s lyrical style. Something about the group captured the imagination of the disaffected in a way that only Slim Shady had previously — not just their willingness to offend but the delight they took in the delivery of the message itself. And like Eminem, Odd Future wasn’t combative in order to rake in the response; more often than not, they seemed bored and disinterested in the impression they made. Instead, their insults were simply the vehicle that their teenage wits had the most fun driving.

While Eminem’s ethos permeated throughout the group in their early days, it was Tyler, The Creator who first exceeded the derivative-if-enjoyable pastiche. The center of a loose, amorphous posse that eventually escaped his pull, Tyler drew the most attention of the group for being the most of everything: boisterous, cunning, cold. His first two albums, like Em’s, were indulgent, introspective, preternaturally-brilliant collections of angst-ridden journal entries walled in preemptive self-awareness. They are largely self-produced, singular statements with only the slightest light let in by other voices or perspectives. Both received critical adoration in equal measure with damning condemnations within the same circles.

While it was evident that each artist was working through considerable internal trauma and conflict, their expression of such took shape in juvenile potshots and cantankerous defiance. Like Eminem, Tyler wielded his undeniable, externally-validated talent as license to live in his own world, one where he could claim himself above the petty squabbles that he presumed concerned the rest of us, and then further above our own standards of decency. While pressure-cooked malaise with little consideration for the sentiments of others has led to some of the most universally resonant art of the last few decades, Tyler pushed himself into a corner that left him with very little of an audience willing to accept him completely. His unapologetic lyrical extremities alienated anyone who listened to music from the center, but his rampant homophobia and violently misogynistic storytelling pushed against the more progressive audiences that would otherwise be most likely to grant leeway to his horrorcore fantasies.

The defense Tyler inherited from others who’ve tried to answer for their callous language while proclaiming a higher moral ground was as such: that his use of gay slurs was evidence of his advanced tolerance, rather than an articulation of ingrained bigotry. The argument usually goes as follows: “Words are just words, and your anger is what gives them power, so just shut up and let me use them.” Or alternatively, how could Tyler hate gay people — the conversation fixated on what his words say about him rather than the harm they inflict on others — when he’s in the same crew as Syd and Frank Ocean? There’s precedent to this type of non-apology, even the promise of increased admiration, Exhibit A being Eminem’s oft-touted, fault-absolving Grammy performance with Elton John.

But even if Tyler’s choice of language wasn’t already being aged out by his generation alongside his rise in popularity, there was an inherent flaw in his plan to repurpose Em’s once-legendary shtick. Where to many listeners with an outsider’s view of hip-hop Slim Shady’s skin color gave his vulgarity tension and ultimately absolution, Tyler’s obscenity wasn’t treated as similarly subversive because it played into the public’s existing stereotypes of young black men. Where Eminem’s been welcomed by the Recording Academy for every solo album he’s ever released, Tyler scored his first Grammy nomination as a lead artist only after abandoning the script that won his predecessor that same award six times. To praise Tyler’s palpable creative energy was framed as validation of a long-standing strand of problematic expression, one where the guilt only ever falls back to condemn the person of color crafting the art and not the predominantly white fans eager to decontextualize the content and sling verbal death threats in a setting that won’t get them reported on Internet forums.

Eminem invaded a public consciousness that wasn’t used to viewing its white representatives as negative influences, doing so by hyper-stylizing a black art form into a near-gimmick that rarely found mainstream success until cast in a paler shade. Doing so, he became hip-hop’s most popular icon and its greatest crossover, a white rapper with credible skills that wasn’t selling just because of his skin color — one who would never be policed for the implications of his content. Black rappers are seen as criminals at baseline; meanwhile Eminem literally has a song called “Criminal” where on the chorus he shouts “Cause I’m a criminal!” and people still won’t consider the notion seriously. Tyler, The Creator was banned in the UK for the lyrical content of music he had then released six years ago; Eminem headlined Reading & Leeds for the third time last year.

Eminem’s had no incentive to change his tune since the beginning of his extremely lucrative career, but he’s in recent years been reckoning with how to reconcile his now matured beliefs with the foundations that established his early appeal. His targeted fanbase has always included the socially-repressed non-oppressed — the kinds of kids likely to grow into “Men’s Rights” activists or call you a snowflake for not considering trolling a valid political ideology. While Eminem made unprecedented, important music in the early 2000s, he did so for an audience that often defined itself by their opposition to other audiences. He’s now doing everything in his power to clear up who he stands for, but the symbols he’s become defined by have already escaped his control. Will the knowledge that Eminem doesn’t support Trump stop Trump supporters from attending his shows and appropriating his songs as their own anthems? Seems unlikely.

Tyler, The Creator was initially headed down a similar path, one where his concerts were largely uninhabitable for the young POC kids who could connect with his lyrics of abstract ostracization, but not the misplaced rage directed at them by the fans Tyler’s scornful, gratuitous use of slurs attracted to his shows. The music of Odd Future was enormously resonant for those who came of age hating who you are yet still finding yourself preferable to everyone else around you; the group channeled relatable ill-will at missing fathers, religious resentment, and criticism received for deviating from the norm, and seemed to make noise as much to block out the cacophony of those they disagreed with as to call out for the few they hoped would understand their frustrations.

Yet instead of using his growing platform to help others navigate the fearful anxiety reinforced by the world around them, Tyler took up the mantle of the most intimate voice shouting them deeper into their own heads. He has dedicated songs to dismissing his fans’ idolization of him as a bother, and worse, marked their connection with his music as pathetic. Listening was tantamount to dodging bullets on a tightrope — struggling to reconcile the healing of hearing someone broadcast from the same headspace as you with the additional harm in them using that wavelength to exclude your empathy.

But soon enough Odd Future began to splinter, and with them, the considerable hoopla surrounding their controversial popularity faded into periphery, each member eager to shed the notorious label the group affixed to their still young careers. As a result, Tyler no longer had the validation of critical attention giving him a pass on his hyperactive hedonism, and over the course of his last few albums he’s since diverted from his path in Eminem’s draft to explore a far more interesting ambition to be himself — whoever that is, being worked through and determined in real time.

Tyler’s always been open about being uncertain of his own identity; his music is an uncomfortably transparent, relentless head rush of self-discovery. Take his mainstream breakthrough Goblin, which opens with a six-minute shadowboxing session where he laments being misunderstood and pigeon-holed, such as refuting his early “horrorcore” label and bemoaning that “I don’t even skate anymore.” He doesn’t have a hold on who he is, but he’s adamant that he’s not all these other things we believe him to be. “My friends really think I’m playing when I say I need counseling,” he trails off toward the end of the song, playing the line for laughs while sincerely dejected in search of someone who’ll believe him in spite of himself.

Goblin is also filled with unruly mudslinging delivered with the charm only a teenager can muster while cursing in all directions. “Kill people, burn shit, fuck school” is such a wildly obvious and dramatized taunt rendered entirely meaningless, but Tyler still felt the need to hammer the point by bookending the song with parental-advisory disclaimers that he didn’t mean what he was saying. Or at least he didn’t mean what his sentiment would naturally be misinterpreted as. “Radicals” isn’t an anthem of retaliation, but rather self-immolation; you have to purge everything else to discover what’s left of yourself. Tyler’s entire discography, which constantly drew lines in the sand around all that he didn’t want to be defined by, was really an attempt to figure out the shape of the box he himself occupied.

Last year’s Flower Boy is what’s left of Tyler. The preceding albums Wolf and Cherry Bomb found Tyler retreating into his own silo, challenging his production mettle to more expansive reaches while easing up on the murderous wordplay as to prevent his thoughts detracting from the sounds. They were the moments his ambition began to exceed his worldview. And after diving deeper into an amorphous mass of brilliant music often poorly strung together, with some fragments of his unflattering animus still stubbornly in place, Flower Boy is the album where his worldview finally caught back up.

That evolution was a long time coming, and ultimately inevitable for the sustainability of Tyler’s career. It’s been almost a decade since the rapper first broke into the zeitgeist with his attention-seizing Bastard, the same year Eminem returned from his mid-aughts musical hiatus with the sobered-up but still reckless Relapse. In that time, the hip-hop world has shifted dramatically for artists in their respective lanes.

Two trends in particular stand out, the first being the aesthetic makeover of the successful white rapper. Where mirrored images of Eminem’s working-class aggression, like his Shady Records signing Yelawolf, might have been expected to carry the torch of Em’s tactics in the mainstream, we’ve seen instead socially-conscious cornballs like Macklemore and the half-white Logic dominate a format once typified by the “gangsta rap” of the early 21st century. But leaning into music defined by self-serving moral virtue is only a commercially viable option for artists who already have the benefit of the public doubt. There’s a reason you don’t see black artists with a similar sonic and social vision hit the top-40.

The second is the way the community now approaches its worst tendencies. Homophobia was not yet a news topic by 2009, but still largely the norm. As a culture, we’ve since moved the needle on what we consider socially permissible to deride. Pushing that change forward, or perhaps resulting from it, has been a rise in the number of artists reclaiming their sexual orientation on record. Some, like Tyler’s former beneficiary Frank Ocean, have done so with graceful ambiguity, while others, such as the members of Internet-arranged “boy band” Brockhampton, have advanced the conversation in nothing short of giddy defiance.

The latter is the most recent and exciting development in this pole-shifting period of rap, as they practice the same loud-mouthed kinetic chaos as both Odd Future and Eminem, but have done so in an emphatically queer way — proclaiming boldly and often their infatuations with pretty boys like Shawn Mendes and Harry Styles, and boasting salaciously about getting head from their boyfriends. They’ve made it feel more fun to be unabashedly queer than unashamedly homophobic. Even if they’ve only just cracked the outer edges of the radio, that affirmation of the value of their marginalized identities rings more impactful than the performative co-signs by straight allies we’ve had to otherwise make do with.

Tyler, seemingly incidentally, adapted seamlessly into a movement that was in direct opposition to his previous character. Flower Boy dropped in between the releases of Brockhampton’s breakthrough Saturation and game-changing Saturation II, and aesthetically fit right into what feels like a peak moment of transgression in hip-hop. Brockhampton rewrote Odd Future’s playbook to be more inclusive concurrently as Tyler was leaving behind those same rules to fit in line with what this new guard represents. The shock and awe of Flower Boy comes not from Tyler’s usual pissing off and on every available target, but from his self-diagnosis of that behavior’s root causes. Rather than antagonizing his fanbase as precaution against attempts to deconstruct his psyche, he’s using that audience as his psychiatrist — addressing them directly instead of relying as he did in the past on “Dr. TC” to make a conversation out of his internal monologues.

Those monologues include a metaphorical debrief of his long-stunted sexuality, which he then goes onto flagrantly fly freely in lines like “I been kissing white boys since 2004″ and “Passenger a white boy, look like River Phoenix.” Elsewhere he embraces behaviors he’d have previously used as license to derogatorily brand others, pushing back against the toxic hypermasculinity he once fostered as a requirement of hip-hop credibility: “Look, I smell like Chanel/ I never mall grip with my manicured nails/ I coconut oil the skin/ I keep the top low ’cause the follicles thinnin’.” In 2018, Tyler shows are now amalgamations of misfits of a different, obverse variety: young queer POCs, NPR-listening professionals, romantic introverts, straight men unafraid to embrace femininity. Rather than hiding behind Frank Ocean to nullify his use of violent language, he’s leaving the “I have a gay friend” rhetoric for other rappers to unsuccessfully flip to the public.

Perhaps most importantly, Tyler’s proving that a socially unconventional rapper doesn’t have to squander their reach to a niche. The influence of his newly progressive outlook extends beyond his role as a musician to that of a cultural mogul. While staying true to his original appeal in his subversion of traditional industry double-speak and a passion for making things that look dope, Tyler is opening up previously gated domains such as streetwear culture and Adult Swim for new communities to enter; for example, by releasing a trio of light pastel Converse dotted in florals and making it as exciting as any Jordan or Yeezy drop, or in the personal soul-searching his new TV show The Jellies is built around. The rapid sell-out of his recent Golf le Fleur shoes is evidence that by finally embracing himself honestly instead of defining himself by who doesn’t know him, Tyler’s become one of the most exciting figures in rap’s long-necessary identity outreach.

His catalogue as a whole may now stand as our greatest musical document of navigating the millennial conflict between social nihilism and internal idealism. As an evolution, it’s a remarkable one, with Tyler going from wielding slurs to self-identifying with them, to abandoning them altogether when he realized his identity was deeper than what was characterized by his loaded language. He’s been the kid who’s self-doubt translated his attempts at friendship into punching-down, but he’s now the classmate dying his hair blue as encouragement for his listeners to be themselves in whatever shape that takes.

It’s the role Tyler’s always meant to belong. It used to be that if you weren’t with Odd Future, they were against you. But somehow Odd Future aged into one of the most diverse formations of artists shaping the hip-hop and R&B landscape in their own image. Fans who typically weren’t welcomed in spaces run amok by their rampant glorification of sexual violence and bigotry are now flooding the roster’s various ranks — proudly taking their place at the main stage of Frank Ocean’s festival-headlining sets or reclaiming the clubs the members of the Internet have now come to control. Now Tyler has shifted his own narrative in Odd Future’s unique story, achieving a brand reversal within the once strict lines of hip-hop credibility that he has helped blur. Eminem became famous for who his music excluded, and it’s a legacy he’s since been unable to renounce in his latter-period career. Tyler thankfully grew up faster, and has now come to redefine his own legacy by everyone he’s let in.