We love this classic cover story on Chance, but in May of 2016, we profiled him again, alongside Lin-Manuel Miranda, the producer of Hamilton. You can check that our right here

When 20-year-old Chancellor Bennett, a.k.a. Chance the Rapper, hits the stage at the Fillmore on an unexpectedly cool July evening in Detroit, he does so with dramatic flair—racing onstage, he skids to the mic and staggers a few steps past it before recovering, like a cartoon character. Even though he has an air of spontaneity and his songs sound unforced and natural, his motions have a deliberate, practiced precision. He’s not only a born performer, he’s a careful one, who studied the work of his idols, from Michael Jackson to Kanye West.

Tonight he’s opening for Earl Sweatshirt and Mac Miller, and the audience—as it was in New York City, and as it will be in Cleveland and at 22 other tour stops—is young, mostly Caucasian, and overwhelmingly female. In other words, it’s the audience that brought Mac into the game. There is some overlap with Chance’s fan base, but for the most part, these are strangers who need to be won over. Chance has a charismatic, exuberant stage persona that easily earns converts, as he’s proven in his native Chicago. He’s in continual motion, lunging, mugging, and dancing to the strains of “Smoke Again” in coordination with his DJ, Oreo. The fans in the audience who know his songs make a show of rapping along as he performs tracks drawn primarily from his acclaimed second mixtape, Acid Rap, released in April. Beyond Chance’s musical gifts and his crowd-pleasing energy, there is a sense of a growing intellectual restlessness on the record: “Used to tell hoes I was dark-light/Or off-white,” Chance raps on “Everybody’s Something.” “But I’d fight if a nigga said that I talk white/And both my parents was black, but they saw it fit that I talk right.”

Chance attended a selective-enrollment high school in downtown Chicago called Jones College Prep. He was raised by two supportive parents, both of whom work in government: his mother, Lisa, in the office of the Illinois attorney general, and his father, Ken, as regional director for the Department of Labor. As a teenager, Chance interned for several political campaigns, including Barack Obama’s first run for president. “I wasn’t a higher-up anywhere because I was like fucking 17,” he says, though he did meet the president several times. “I was there, you know, in the battlefield. Trying to create change.”

Chance is unapologetically middle class, and extremely honest about this fact in his music. His outlook on life is endearingly innocent. On his 2012 mixtape debut, 10 Day, however, that earnestness could come across a little precious. Inspired by a suspension he received during his senior year for smoking weed, 10 Day includes songs with titles like “Prom Night,” “Nostalgia,” and “Hey Ma.” It feels cloying at times, infused with the sentimentality of a yearbook note to a good friend.