“I do regret it,” the rapper Rich Chigga said, of his stage name, as he sat in a smoky greenroom backstage at a club in Manhattan. Chigga, a seventeen-year-old Internet star, was born and raised in Jakarta but is of Chinese descent, hence the portmanteau. This was his first trip to the United States; he was here for a concert tour. Chigga got his start by making short, comedic Internet videos, and found viral fame with a 2016 rap single called “Dat $tick.” But he wants to be more than a seemingly naïve Asian rapper who became a meme: he wants be taken seriously as a “real” rapper. Having watched his videos, I was curious to see Chigga in person, though it made me queasy to pronounce his name, given its breezy proximity to a racial slur. Instead, I told my friends, “I’m going to see an Indonesian rapper.” Anything to avoid articulating the curious and problematic persona that Chigga presents when he peacocks across your laptop screen in one of his kooky and hallucinogenic music videos. The videos typically combine rap-video tropes (expensive cars, beautiful women) with Internet catnip (Chigga on a hoverboard, flames trailing behind him). They are unforgettable in the way that unexpected mash-ups can be. And now, at last, Chigga was at S.O.B.’s, in New York, facing his audience I.R.L.

Chigga’s real name is Brian Imanuel. Although he is slight and wiry, he raps with a sonorous and imposing voice. The music video for “Dat $tick” showcased this incongruity. Imanuel sports a baby-pink polo and a Reebok fanny pack over baggy khaki shorts as he raps lyrics like “I don’t give a fuck about a mothafuckin’ po / I’ma pull up with that stick and hit yo’ mothafuckin’ do.” The song is just two minutes long; Chigga saunters down a tree-lined residential street as two members of his crew wave guns behind him. He pours a bottle of Martell Cognac menacingly onto the asphalt, in slow motion. It’s difficult to parse what’s happening onscreen—whether this crew of Asian men, performing clichéd masculine toughness, is meant to be humorous. But fairly quickly your suspicion is overtaken by the fact that the track is actually pretty good. The video found viewers after Imanuel’s management group, 88Rising (which is Brooklyn-based but focussed on Asian music), released a video in which Cam’ron, Ghostface Killah, Desiigner, and other U.S. rappers react to the video, expressing bewilderment and gleeful fascination. They are largely positive about the song’s driving beat and Imanuel’s flow. “That’s my nigga, that’s my fucking guy!” Jazz Cartier says, laughing. Naturally, there’s apprehension, too. “He found a way to say nigga without really saying it,” a member of the Flatbush Zombies quips.

“Dat $tick,” though infectious, can seem like a burlesque of the kind of popular rap, conceived and performed largely by black artists, that Imanuel grew up listening to. Like his name, the track is an enthusiastic but discomfiting homage that raises questions about appropriation and sincerity. In an interview with The Fader, Imanuel called his handle “this ignorant ass name” and admitted, “I didn’t really know what I was doing and I definitely did not know people were gonna pop off like this.” Imanuel is regularly chastised on Twitter as a racist, but it’s hard to imagine that he would have been able to fully comprehend and negotiate the complicated racial and artistic politics of a different country on the other side of the globe, watching hip-hop videos on his laptop and learning English from YouTube. In response, Imanuel told me that he’s stopped using the N-word in his songs and has modified his approach to writing lyrics. “I’m trying to avoid writing about guns and killing people in the new songs,” he said. “I want to write from my own experience.”

That seems like a tricky path forward, given that his experience is of being a middle-class kid from Asia—not the traditional material for the genre. The last Asian artist to so widely capture Western attention by rapping, after all, was PSY—the Korean singer and rapper known for the viral dance classic “Gangnam Style”—whose song relied on a goofy lightheartedness, more akin to slapstick than to hip-hop. The recent documentary “Bad Rap” explores the challenges that stand in the way of Asian-American rappers who chase mainstream success. In the trailer, the rappers Awkwafina, Dumbfoundead, Rekstizzy, and Lyricks—all of whom are Asian and were born and raised in the U.S.—voice a laundry list of identity-based concerns: “Out of a hundred rappers, there’s like five Asian-American rappers”; “What's this whole business of sounding ‘black’?”; “They expect us to be a model minority.” One of the unusual things about Imanuel is that he seemed to materialize out of nowhere, mostly isolated from the assumptions and contexts that accompany rap in the West, and rose fast enough to nearly skate by questions of appropriation or identity. “I don’t know why you should put all the Asian rappers together in a box,” he said. “It’s kind of like you’re putting them away from the others.” When reminded that going by the name “Rich Chigga” inevitably brings race to the forefront of his act, he said, “That’s really why I hate it. It has race in it.”

In a moment when the act of articulating identity seems both urgent and fraught, there’s something comforting about the expanse of contradictions delivered without an answer by this suddenly famous teen-ager from Jakarta. The attendees at the first set at S.O.B.’s were mostly teen-agers: black, brown, and Asian kids in the kind of dress that made it seem plausible that they were actually hip to the rap scene—plus a few young men dressed in Imanuel’s viral-video uniform, complete with fanny packs. One twentysomething said that he enjoyed himself but couldn’t see Chigga advancing past meme-rapperdom. “He should stick to being funny,” he said. Standing nearby were scouts from the Sony Red label. “We think he could be the real thing,” one of them told me.

The late show, which was slated to begin at ten-thirty, drew mellower fans. High-school students complained about having to get up for school the next day; young professionals marvelled aloud at being out so late on a Wednesday night. At midnight, Chigga took the stage, opening with his song “Back At It.” On finishing, he gushed to the crowd about his arrival in New York: “I got here and I was, like, ‘Holy shit, I’m really in America!’ ” he said. He made eye contact with the first row, full of young women. “You guys are looking so pretty tonight,” he said, to raucous cheering. The moment could have seemed smarmy, but it read as sweetly ingenuous—a tone that suffused the rest of his performance. At one point he played another rapper’s song, just because he liked it.

After Imanuel performed his full repertoire, which amounts to only five or six songs, the show began to wind down. He had yet to turn to his big hit single. “This isn’t one of my best songs,” he finally said, “but I think you’ll know it.” He launched into a frenetic performance of “Dat $tick.” A monitor near the stage that faced the audience captured the scene: a purple mist of fog swirling around a very young, very skinny Asian man as he prowled in front of a screaming, leaping crowd, made up mostly of Asian-Americans, who pumped their fists to every word.

There was heavy silence when he finished. “It was so nice to see everyone in real life,” he said. The crowd booed, hoping for more. “Those are all the songs I’ve got!” Imanuel protested. He paused for a moment, taking in the longing cheers of the crowd. “O.K., O.K.,” he purred. “I think you guys are ready for another song.” A familiar icy beat rang through the auditorium, and Imanuel threw his body forward, into another performance of “Dat $tick”—this time, the remix version. The audience surged. When they chanted, they used his given name, Brian.