Tyler, the Creator leaps onto Jimmy Fallon’s back and hangs there like a hyperactive kid at the zoo. It’s 2011: Instagram is in its infancy; young people are choosing the internet over television en masse for the first time; Tumblr has nearly tripled its audience in a year. Tyler just performed “Sandwitches” with Hodgy Beats on NBC’s “Late Night”—both representing the collective Odd Future Wolf Gang Kill Them All—and this mischievous URL rap tag-team turned Studio 6B into a scene from The Ring. Entire verses of the song wouldn’t be performed on TV that night, but the omission of one lyric in particular felt impactful: “Free Earl, that’s the fucking shit/And if you disagree, suck a couple pimple-covered dicks.”

This was the crest of Odd Future mania: Tyler had released “Yonkers” (which Kanye West called the best video of the year) only days before, and the enigmatic Frank Ocean dropped his debut mixtape nostalgia, ULTRA without warning the night the “Fallon” episode aired. Rap’s monied old guard, JAY-Z and Diddy, were in a bidding war over the young crew. The media began nitpicking the collective’s grisly lyrics and struggling with the ethics of taking trolls at face value.

Despite a growing public profile, the kids of Odd Future were too caught up in their fringe internet communities to really notice; too busy squabbling with rap blogs that wouldn’t post their songs, or responding to fans’ questions on formspring, or relishing very online achievements like “going platinum on YouTube,” or literally predicting future VMA wins on Twitter. But looming larger than the collective’s rapidly expanding reputation was the silhouette of Thebe Neruda Kgositsile, an enigma known to OF onlookers as Earl Sweatshirt. He’d been AWOL throughout the group’s breakthrough with little to no explanation. “I wish Thebe was here to share this moment with us,” Tyler tweeted right after the “Fallon” performance. Even in his absence, Earl was still the wind in their sails.

So much of the hysteria surrounding these Los Angeles punks stemmed directly from “Earl,” the title track from the 16-year-old Earl Sweatshirt’s self-titled debut mixtape, released by Tyler for free on Tumblr in March 2010. Earl was slickly sinister yet designed to draw out a visceral reaction—American Psycho meets “Jackass.” And “Earl” was its lynchpin: gorgeously crafted sesquipedalian stanzas with gags about jacking off to Asher Roth vids right next to depictions of killing and eating people, the words scraping up against each other like fractured bones. In its semi-viral music video, under the glare of a grainy fisheye lens, Earl and his OF cohorts use a blender to concoct a drug smoothie out of weed, pills, cough syrup, and malt liquor before puking it all up. They skate, loiter, faceplant, and spit out blood and teeth. The juvenile, almost slapstick images betrayed the seriousness of Earl’s violent claims, as if watching an unaired “Loiter Squad” pilot. But the gambit had worked: Adults were mad, ergo teens loved it.

In Earl’s inexplicable absence, his comrades began cryptically roaring “Free Earl” while vaulting into the crowd at their sold-out shows, creating even more buzz and mystery around the already surging, inscrutable collective. (The chatter online was that Earl’s mom caught wind of the “Earl” video and had shipped him off to boot camp, a perceived totalitarian move that only fed his legend among Odd Future’s rabble-rouser fanbase.) Everyone wanted to know why the boy genius was missing. By the time he’d been found, Odd Future had already used his echo to become an indomitable rap force—and Earl had already become someone else.

Unbeknownst to most of his faithful, Earl Sweatshirt was the son of world-renowned poet Keorapetse Kgositsile and UCLA law professor Cheryl Harris, a union that seemingly prophesied his eloquence. According to the 1995 poem, “Poet — for Thebe Neruda,” written by Kgositsile’s friend Sterling Plumpp as both a tribute and a baptism, Earl was marked as a bard-king-in-waiting at birth: “You were born with blues With an ANC [African National Congress] imprint on them,” it said. “How you gon do anything but rule?”

But after Earl’s parents separated when he was a child, his father became a dark cloud forming just on the outside of his life. Earl’s early self-indictments tied his misfit motivations directly to an estranged relationship with his dad. “I’m half-privileged, think white and have nigga lips/A tad different, mad smart, act ignorant/Shit, I’ll pass the class when my dad starts givin’ shits,” he explained on “Blade” from the 2010 Odd Future tape Radical. “But as long as our relationship is turdless/I’mma keep burning rubber and fucking these beats with burnt dick.”

By chance or by choice, Earl had followed in Kgositsile’s footsteps anyway, fulfilling Plumpp’s vision. He picked up rapping in eighth grade, releasing a mixtape on Myspace under the name Sly Tendencies called Kitchen Cutlery. His raps were more sinewy then but no less of a marvel. It wasn’t until after Tyler discovered those Sly songs that Earl’s verses took a turn for the diabolical, positioning him as “the reincarnation of ’98 Eminem,” as he put it on Tyler’s Bastard cut “AssMilk” in 2009. He idolized Tyler almost as much as he did Em, and Tyler recognized instantly what the rest of the world would soon know: Earl Sweatshirt was a wunderkind. He liked to compare Earl to Nas’ Illmatic, and he wasn’t that far off base.

Earl had been recruited into a fraternity of mutineers who treated Supreme like haute couture, who made Eminem’s Relapse their unholy bible, who worshipped Lil B and skate pro Jason Dill as gods. They were contrarians goading moralists into reacting to their stunts, drawing life from the discomfort of others. For them, watching the squirming responses to their provocations was proof of a hopelessly stuffy society. “We’re not trying to offend or intrigue people,” Syd told Interview in 2011, one of many attempts to explain how a queer black woman could surround herself with so many perceived homophobes and misogynists spouting rape fantasies. “It’s more of a social experiment. We make fun of society on a daily basis, and people take it so seriously. They’re proving us right.” But more important than the jokes themselves was the fact that they were sharing them, finding fellowship and bonding into a collective.

One of the foundational tenets of Odd Future was mining power from being fatherless and building a chosen family in their little Thrasher community. Earl found Tyler’s IDGAF attitude empowering, and emulated it. In each other, they found brotherhood, making it their aim to “scare the fuck out of old white fucking people that live in middle fucking America.” (Ironically, their early audiences were usually majority white.) For Earl, that meant saying the sickest shit he could possibly think of with a straight face, screaming internally while he measured out multisyllabic scenes of torture and cannibalism.

In Sterling Plumpp’s ’95 poem to Thebe Neruda Kgositsile, he wrote, “Words are bullets here. Words are periods here. This is the end of a sentence,” and that’s exactly how Earl uses them: to perforate; and with resolution.

The verses on Earl are unspliced one-shots that impact instantly and then peel apart gradually. While many wordy rappers assemble bars as if reading from a schematic or like they’re noodling through a bowl of alphabet soup, Earl’s raps are idiomatic yet undiluted, technical yet unpredictable. He can be a methodical writer or a shapeshifter: On “Kill” he’s first trampling, then sinuous, then supple; chilling, then surgical, then irreverent. More interesting than his penchant for colorful dismemberment, or the incel logic on songs like “Luper,” is just how uncomplicated he makes complexity look.

Earl was the keystone to Odd Future’s success. It’s where their anarchist slogan—“Kill people. Burn Shit. Fuck School.”—first appeared. It’s the source of their edge, constructed on myths of the boy whose music was so dangerous his mother wouldn’t let him make it anymore. But more essential than any of that was its author: This prodigiously gifted kid, the son of a UCLA law professor and a world-famous poet, who had unleashed this almost otherworldly display of technical skill from the ether into an unsuspecting (and frankly unprepared) universe. His knack for storytelling was obvious, only his stories were night terrors about stalking, assaulting, and killing women. It was a jarring juxtaposition: his stoic manner, his beautiful wordplay, and his ugliest ideas, all underscored by dueling intentions—to taunt and to purge. There was a blatant disconnect between the rage in his words and the affectlessness of his demeanor, which at points made him seem either like a sociopath or a tempestuous virtuoso completely spent of energy from wrestling his inner demons. Over beats from Tyler and Left Brain, Neptunes paeans transposed for horror scores, he spun the most breathtaking nightmares.

Of course, some of the more vile diatribes on Earl were simply the result of a rapper employing shock-rap tactics and pushing the boundaries of acceptability, but the tape also showcased an angry kid who didn’t yet have the language of grief trying to process his feelings. He’s talked since about not having the capacity, at 16, to really rap about anything real, unable to use that piercing wit of his to look inward. “There was never a moment where I was trying to fucking perpetrate like I was some [rapist],” he told GQ. “That was my way of screaming, because I don’t yell.” Through these quiet atrocities of the imagination, he was gnashing his teeth.

Being 16 is being old enough to know better but young enough not to care, which is the sweet spot for an aggrieved imp spewing poison back into the world just to feel something. His raps bared that animosity in them. Plenty of the ire was aimless, but much of it was stoked by feelings of fatherlessness. His later verses on the subject, which are more clear-headed, present a tragic portrait: A father and son, both gifted orators, unable to really understand each other. On Earl, there are glimpses of him converting his anguish to rage, so as not to be consumed by sorrow. “Product of popped rubbers and pops that did not love us/So when I leave home keep my heart on the top cupboard/So I will not stutter when I’m shoutin’ fuck you, son,” he raps on “Stapleton.”

Somewhere along the line, raging on songs turned to causing real-world mischief. And so, just on the cusp of Odd Future’s swelling success, soon after the “Earl” video was released in May 2010, Earl’s mother sent him away to reform, and to heal—first to Second Nature, a wilderness program, for a few weeks, and then to Coral Reef Academy in Samoa, a therapeutic rehabilitation experience for at-risk boys. “He was really very clearly going through a rough patch emotionally,” Harris told The New York Times. “He was struggling.”

While Odd Future followers chanted “Free Earl” at shows and plastered the words across forums online, vilifying the rapper’s mom in the process, Earl was hearing stories of abuse from survivors, first-hand accounts of the kind of gruesome things he’d been rapping about. It changed him, made the things he’d been saying in songs real. And so he vowed to never be so blasé about the suffering of others again. “I’m a fan of macabre shit, you know what I’m saying? But not like that. At the end of the day, I’m not some evil guy,” he told GQ in 2013. “There was nothing you could do when you’re looking at a fucking little girl that’s been horribly abused.”

When he returned from Coral Reef in 2012, after being found out by Complex, it seemed like trying to fit his new self back into his old life came with major growing pains. Assimilating back into Odd Future proved difficult after more than a year of therapy; not just because he’d become something of a mascot to the fandom, but also because he’d always been the crew’s catalyst, the sorcerer among mortals. (“Tyler always treated him as sacred,” Odd Future manager Christian Clancy told The Times. “They all did.”) Tyler was the architect, but there was never any doubt who the best rapper was. Upon arrival, Earl was already one of the most purely talented rap writers of all time, bar none. He was a scalpel wielded by the collective to carve OFWGKTA into the collective consciousness. But now, he was seeking a different legacy.

In less than two years, he went from hailing “Earl” as a shining treasure, the track he thought he’d never be able to surpass, to shunning the song as something he couldn’t even listen to, likening its sound to skinning a knee. He performed alongside his friends at first but didn’t sign to Odd Future Records. The tug-of-war between his mother and best friend, compounded by the cultish fandom that rose up while he was overseas, had blemished his OF residency and made things awkward, alienating him from a makeshift family that was already beginning to dissolve. The riff had grown into a chasm. He was back, but he was already gone.