Young Thug, a twenty-three-year-old rapper from Atlanta, embodies the new digital era in which record executives are still trying to find their place. Photograph by Johnny Nunez / WireImage / Getty

“I need all building lights off, building lights off, building lights off,” the rapper Young Thug says as he directs the crowd at the PlayStation Theatre, in Times Square, an hour into his set. The crosshatched beams soon dim, followed by a large plasma screen cycling through images of Prince. The night has been a tribute of sorts—earlier, Thug had emerged sporting a flowing white blouse, lace gloves, and a microphone fixed with Prince’s “Love” symbol. “I need all the phone lights on, phone lights on, phone lights on,” Thug continues in rhythm, and the audience raises a constellation of white flashlights shining from their phones. A few girls toward the front have outfitted their phones with cases that glow around the entire frame, like a camera-equipped vanity mirror. “What the fuck kind of light is that?” Thug asks, as if he has spotted a device from the future. “O.K., now, look,” he continues. “I don’t care if it was your mother, father, sister, brother, grandma, grandpa, cousin, auntie, uncle, ancestor—someone did a lot of shit for you to live this lifestyle.” A flutter of piano chords swells from the d.j.’s laptop, and Thug tears into his crossover hit, “Lifestyle”: “I got a moms, bitch, she got a moms, bitch,” he raps in his signature shrill warble. “I got sisters and brothers to feed.”

The audience is sixteen and up, but not by much. They belt the lyrics along with him, while trying to hold still long enough to film clips of their otherworldly hero making a special appearance on Earth. The crowd has been mobile the entire evening, seizing the theatre like a high-school assembly where the principal never shows: darting from seat to seat, sprawling on the floor, cuddling in dim corners, dancing by themselves, throwing shoes, lighting joints, dodging security guards, sweating, screaming when they feel like it. Near the merch booth, a young man is swarmed when he unveils a box of pizza that he had somehow smuggled past the ticket scanners. Tidbits rise above the din: “What school do you go to?”; “I think I feel it hitting me now.” Back inside, a couple is arm in arm. The boy sports a backward baseball cap from Kith; the girl sways with willow-straight hair. They pass a vape pen back and forth. “I know a lot of y’all are young and in school and all that,” Thug says. “But make some noise if everything you do is ’bout the money!” Their arms shoot up, and then tangle into each other’s.

I notice the record executive Lyor Cohen watching from the sound booth, tucked away and stoic among the fans too young to recognize him. He had emerged from backstage late in Thug’s set to monitor the performance. Thug means a lot to Cohen: he’s the marquee artist on 300 Entertainment, the shiny new digital-focussed label that Cohen resigned from his post as chairman and chief executive of Warner Music to co-found, in 2012. At the same time, Thug and his ceaseless flow of mixtapes have come to represent a counterstrike on the kind of music that Cohen helped canonize, and the promotional methods that he has mastered. For fans of Run-DMC, Public Enemy, the Beastie Boys, and other iconic acts guided by Cohen during his decades at Def Jam, Thug’s incessant vulgarity and garbled delivery represent a cultural backslide. This tension came to a head in a news segment that aired in April on CNBC, in which Cohen and Thug sparred across a conference table. “I understand that you’re shy and you don’t like doing it, but your fans need to hear from you,” Cohen said, prodding Thug to do more interviews. “I don’t want everybody just to know,” Thug shot back. The label exec moved on to song development: “You just record so many songs and leave them like little orphans out there. You have to come back to them.” The rapper again stood his ground: “The critics come back to them!”

In the theatre, Cohen’s looming frame seems restless—as if he wants to prove the naysayers wrong, and wants Thug to do the same. As the rapper rocks on, Cohen shifts his weight: holding his hip, leaning against the board, leaning on a chair, glancing over his shoulder toward the crowd behind him to take in the sea of phone lights that Thug has just requested. When Thug launches into “Best Friend,” a sweltering, trudging single that he recently disambiguated, for GQ, Cohen loosens a bit, appearing relieved. The artist onstage finally seems like one he can sell—one he can recognize. He starts to bob his head.

Two nights later, Justin Bieber tells an arena of screaming fans at Barclays Center, “I’m going to do a song a lot of you might not know.” Seated on a red couch that has risen from a stage that won’t stop shape-shifting, Bieber takes off the white bandanna that he has sported throughout the evening, and strums his guitar. “Look up at the stars with me tonight,” he sings, “and everything will be all right.” Thousands of screaming girls raise their phones, this time unprompted. The white dots sway and pulse from the pit to the nosebleeds—looking up at the stars is the opposite of looking down at your phone, but here the two are inseparable. Somewhere along the line, musical artists stopped asking their fans to put lighters in the air. The iPhone lights are brighter and stay lit longer, and none of the kids in this crowd should have a lighter anyway.

But maybe the silicon stars have distracted Bieber, because he skips his next song, “Love Yourself,” in error. It’s one of the singles that fans have shown up to hear, along with “What Do You Mean?,” “Where Are Ü Now,” and “Sorry,” all mammoth hits from his 2015 album, “Purpose,” which has kept the Bieber machine running through what would have been his senior year of college. “I got a bit ahead of myself,” Bieber laughs, before stagehands bring back the sofa and the guitar and he leads the eighteen-thousand-teen sing-along to “Love Yourself” that many parents have paid for.

Although Bieber arrived as the archetypal social-media superstar, his career arc is unquestionably indebted to the pre-Napster, multi-platinum tenures of record execs like Cohen and icons like Prince—and Michael Jackson, whose songs float from the Barclays house speakers between sets. Watching Bieber perform distantly and coldly, twice skipping a song in his set and missing a dressing cue, one can’t help but wonder whether Prince or Jackson would ever deliver such a performance. I don’t mean to impose an unfair comparison on Bieber, but he sort of demands it, and on this evening he falls so nonchalantly short of these idols. “This is the intro I was trying to get into earlier,” he explains after his second slipup. “Do you guys ever feel like sleeping all day?”

Watching the show, my mind returned to Cohen’s gaze at his latest protégé, a twenty-three-year-old from Atlanta. This Bieber amateurishness might have been the moment that Cohen feared, when watching Thug. The thirty-year career that Cohen has spent cultivating the best talent, hiring the best personnel, and helping to elevate the best music, with quantifiable results and timeless appeal, appears null and void in a new era in which he is still trying to find his place. It was an unease felt earlier that evening during a performance by Post Malone, who gets to tour with Bieber because of one viral song, “White Iverson,” despite a seeming lack of natural talent or capacity for a follow-up. And yet when Bieber screws up so blatantly, and so frequently, the fans still scream, the check still clears, and you still want to root for him, because who else is there to root for? “I know that I let you down,” the song goes. “Is it too late to say I’m sorry now?” No, Justin, it’s never too late for you.