Rap had never seen an XXXTentacion before. The rapper, who was shot and killed on Monday, was an anomaly for many fans, an artist who rose to prominence despite a publicly reported, stomach-turning series of criminal charges that included domestic battery by strangulation, false imprisonment, and aggravated battery of a pregnant woman. Despite these details—or, it has been argued, because of them—20-year-old Jahseh Dwayne Onfroy quickly became one of the most heard musicians in modern times. His self-released 2017 album, 17, is one of the true sensations of the streaming era, with a song, the portentous ballad “Jocelyn Flores,” that has been played hundreds of millions of times on services like Spotify and Apple Music. His follow-up, ?, was released in March—it’s even bigger. An independent artist with little marketing or promotion to speak of, wrapped in the metaphysical barbed wire of heinous allegations, became a generational voice by dint of those services and SoundCloud and YouTube and a rabid group that tracked his every whisper. Some of his fans were unaware of the allegations. Others were disgusted by them when made aware. Others didn’t believe them. And others still found themselves wracked by indecision about what to do.

X, as he’s colloquially called by fans, quickly became a literal poster boy for a class of rapper the world has not yet figured out what to do with. His mug shot from a 2016 arrest is the misappropriated Che Guevara T-shirt for a new age. His songs—delicately strummed acoustic lamentations and thrashing, distorted anthems—are a clarion call for disaffected teenagers, as wounded and raw as they are dyspeptic and virulent. Think one part Elliott Smith, one part DMX. One of the most difficult things about XXXTentacion was the overwhelming sense many had that despite the controversy and terrifying pain he caused real people, he had something unique: talent.

Talent—songwriting, painting, storytelling, whatever—has an intoxicating power; it can blot out the things we don’t want to see. I remember being enticed by artists like X, with their vast ache and perceptible gifts. His songs had an operatic melancholy, with titles like “Everybody Dies in Their Nightmares,” “Fuck Love,” and “NUMB.” The debate he inflamed with yet more gasoline—bad people and what to do with their good art—has been at a fever pitch for the better part of five years, and it won’t end with XXXTentacion’s life. But he will be mourned by his fans. And there are a lot of them. Some of the worst ones harassed and taunted Geneva Ayala, the woman who says she was the victim of X’s aforementioned crimes. Or they hacked her social media. Or they called her house and yelled at her to drop the charges. “I can’t even go to the mall or Walmart without being noticed and eyed down,” she told the Miami New Times in a feature story on the rapper that was published earlier this month. Not all of his fans are monstrous actors in this tipped-over fishbowl, some are just people who identify with the songs. “I be feeling pain, I be feeling pain just to hold on / And I don’t feel the same, I’m so numb,” X sings on “Jocelyn Flores.” It’s a remarkable and strange song that can’t begin to cope with its own cruel, cosmic irony.

X’s death has happened at a strange moment in rap history, a time when the genre has never been more stratified, more lucrative, more diluted, more misunderstood, more exciting, and more like every significant popular music genre that has come before it—nearing the brink of its dominance. Before the news, June had been defined by a series of releases from a collection of artists currently upending the timeworn notion that rap—and to some extent, all popular music—is the realm of the young. Kanye West, who is 41, released Ye, his eighth album. He also produced albums for Pusha-T, also 41, and Nas, 44. This trio of albums represent three of a five-album set in a series of seven-track projects in his GOOD Music stead. The run has been a fiasco. After the inevitable boom of relevance, all three have been quietly passed by, each one more quickly than the last.

Nas’s Nasir, his 11th album, was released on Friday and it already feels as though it has been resigned to the iCloud in the sky, a fate nearly worse than death. That’s thanks in no small part to Everything Is Love, the surprise first full-length release from the Carters, better known as Beyoncé and 48-year-old Jay-Z, which undermined his old nemesis Nas in a manner not unlike “Takeover” did 17 years ago. The petty album drop recalled old times, when Nas was in search of a comeback and nearly had it in his grasp, when Jay was just entering his 30s, when Kanye West was the overeager backpacker in a creamsicle Lacoste polo yelling in the studio. “Kanye came in and ... did his job. Did he not!?” Jay howled in the documentary Fade to Black, like a papa surprised to learn that his annoying son could throw a 90 mile-an-hour fastball. In many ways, this trio forged the three stages of rapper as icon. And Nas, Kanye, and Jay-Z have almost always been artists obsessed with the prefab components of fame: money, attention, legacy, branded power. Their myths are self-selected: the hustler-made-mogul; the college-dropout-turned-genius; the boy-poet-cum-journalist.

In recent months, I have been thinking about this generation of artists in opposition to a new class. The new group unveiling their myths alongside XXXTentacion include the similarly controversial and bracing New York MC Tekashi 6ix9ine, the late Long Island rapper Lil Peep, Lil Xan, Lil Pump, Lil Uzi Vert, Trippie Redd, and Smokepurpp, among others. There is something unbound, rambunctious, untrained, unfinished in these artists. It’s all on the surface, the tumult and the rejection of respectability: tattoos, two-toned braids, hectoring verses, gentle choruses. Sometimes it feels numbing—the ascendant Lil Pump is both thrilling and soul-killing, the musical equivalent of playing Street Fighter II for 12 hours straight. Sometimes, as in Peep’s case, there is an unvarnished feeling between the bars, a poignancy in the performed pain. These aren’t the children of Odd Future, per se—they’re just our odd future.

Between these two sets, there is a healthy middle-ground generation of successful rappers—Nicki Minaj, Drake, J. Cole, Future, Childish Gambino, Kendrick Lamar, Migos—with trajectories that feel familiar. Global sponsorship, sporting-event halftime shows, Grammy sets, maybe even a Pulitzer Prize. These are stories we know, their aspirations are firmly entrenched, their goals evident on the face of every move. Rap has expanded into every open crevasse of American culture; it’s been the de facto pop sound for more than 30 years. The possibilities are limitless, but time is not forever. Typically, a moment arrives when the previous generation moves on. LL Cool J can no longer be the center of the art form; he has decamped to CBS procedurals.

Figures like Jay and Kanye are different—more emboldened and more successful than their forbearers. This past month is the first time I sensed an indelible and disastrous feeling of age and exhaustion in their work. They have entered a grotesque period, as baroque as it is depressing. It comes for everyone, and now them: Jay, neutered and artistically sidelined by his incredibly powerful and indomitable wife; Kanye, a creatively bankrupt husk of insight. One rapping about wealth in the bowels of the world’s foremost art museum; the other rapping about sex before a bonfire in the wilderness of one of America’s wealthiest communities. The visuals are staggering, and depressing. Someone tell these guys they already won. It’s all over but the shouting.

I will never love a 6ix9ine song or a Lil Pump album in the way that I obsessed over The College Dropout or “Dead Presidents.” That’s by design; I, too, am increasingly irrelevant. But there is a striking sense of change happening in the genre that X’s death only underlined for me. The distinctly queasy feeling of not wanting to listen to his songs, and what doing so would do—provide him with clout, counting numbers, money—has been lifted, for whatever reason. Burrowing deeper into his music has revealed a fissure in the entire genre, something worming around the edges looking to break it clean open. This, of course, is the product of dozens of artists for 40 years expanding and destroying the precepts of rap. From “Beat Bop” to Young Thug, rap was made to be broken. But there is something different here, an abandonment of form, of ambition, of composure and infrastructure. And maybe of safety. X and Peep and their cohort made big music in small rooms with modest reach, independent of the corporate structures that rocketed even the most iconoclastic musicians to fame and fortune. And it still took off. 2Pac feels like the most logical antecedent, but even he was a by-product of an age in which the rebel poet was supported by the conglomeration.

Before his death, XXXTentacion became a bellwether for the role a massive company like Spotify can play in the artistic quagmire at the center of so much culture consumption. When the service removed his songs from its playlists, outcry over double standards and slippery slopes overwhelmed the act. Eventually, Spotify reneged on its promise to remove the artist’s song from all promoted playlists. In the aftermath of his death, I expect X will return to the top of Spotify’s charts, knocking off Jay, Ye, Nas, and the rest. It’s the natural order of things, that much more so when tragedy strikes. He won’t stay there, not for long. But he’s not going to be erased either.