Chance the Rapper: High Times and Wild Nights in Chicago

Hanging with the 20-year-old star behind one of the year's best hip-hop releases

Chance Bennett aka Chance the Rapper
Todd Diederich
Chance the Rapper
By |

On an unseasonably warm Friday evening in May, minutes before facing the biggest hometown crowd of his young career, Chance the Rapper races a skateboard around the barren downtown-Chicago office space that's temporarily doubling as his dressing room. The 20-year-old rapper – dressed in a gray LDRS hoodie, black skinny jeans and mismatched plaid shoes – cracks jokes continuously, pausing only to accept a pot-brownie offering from two teenage fans giving him the thumbs-up through a clear glass window. "I don't know if I should eat this," he deadpans. "I might die."

Moments later, Chance (born Chancelor Bennett) is a different person. He's completely silent, head down, eyes fixed, as he gets ready to take the stage at the college street festival that he's playing tonight. Officially, Chance isn't the headlining act, but the few thousand people crammed into the tent where he's about to perform – most of whom appear to be legitimately geeking out over the rapper's appearance – suggest otherwise.

When he hits the stage, Chance transforms again, this time into a polished performer. He kicks quick, clever rhymes from his acclaimed new mixtape, Acid Rap, accompanied by manic, twerking dance moves. The crowd loves it. "When you get pissed, promise you're just gonna smoke again," he says to riotous approval.

Album Review: Chance the Rapper, Acid Rap

A few days later, nursing a blunt on a sun-drenched rooftop on Chicago's West Side, Chance explains how his personality can seem to switch up at such whiplash speed. "Chance the Rapper is many things," says the MC. "I'm constantly evolving. And it's just the beginning."

Chance, who is still technically unsigned, just returned from a five-day trip to Los Angeles. While there, he recorded new tracks and took business meetings with "nearly every major label," including a sit-down with Epic Records CEO L.A. Reid. But for now, he says he's holding off signing with anyone. "There's still more time," he says, "and still so many stages to Acid Rap."

His debut mixtape, 2011's #10Day – written over a 10-day suspension from high school for smoking weed – made some waves among hip-hop fans in the know. But Acid Rap is the rapper's real introduction to the wider world. Recorded in Chicago, with turns in New York and L.A., it encompasses a collage of genres – from jazz ("Acid Rain") to ghettotech juke ("Good Ass Intro") to soul ("Everybody's Something"). Chance's nasal vocal cadences call to mind Lil Wayne and Kendrick Lamar as he ruminates on the diagonal-cut grilled cheeses and Rugrats lunch boxes of his youth and demands an end to his hometown's unremitting violence.

The mixtape's woozy, psychedelic, outside-the-box sound might have something to do with all the acid Chance dropped during the recording process. He specifically recalls one particular trip during which he vibed out to James Blake's minimal "I Never Learnt to Share," ultimately helping inspire Acid Rap standout track "Cocoa Butter Kisses." "You're more inquisitive," he says of his experiences on what he deems to be a much-misunderstood drug. "I won't ever know what Acid Rap would have sounded like if I'd never done acid."

Chance grew up the older of two brothers in the middle-class neighborhood of West Chatham, an oasis in Chicago's otherwise rough South Side. His dad, Ken Williams-Bennett, was a prominent presence in the city: He first served as an aide to former Chicago mayor Harold Washington and then worked for then-U.S. senator Barack Obama. Williams-Bennett, who is now a regional representative to the U.S. Secretary of Labor, dreamed that his son might one day hold office. But Chance was always more interested in the arts, performing in talent shows from his pre-school days through high school at Chicago's esteemed Jones College Prep.

Chance knew he wanted to be a rapper after hearing Kanye West's 2004 debut The College Dropout at age 10. "Kanye took me from a kid who listened to music to a kid who lived music," he says. He spent his high-school evenings perfecting his craft: He performed slam poetry, recorded for free at the local library, attended open mic nights and got deeper into the local arts scene where he met most of the members of his musical crew, Save Money, including rappers Vic Mensa and Kami De Chukwu and rap-rock collective Kids These Days.

After cutting a final exam for band practice, Chance was forced to earn his diploma online. Chance enrolled at Harold Washington College in Chicago. He dropped out a week later, leading to a rift between the aspiring rapper and his father. They didn't talk for months. "I think that's our family's way of showing disapproval," Williams-Bennett says in a phone interview.

The September 2011 stabbing death of Chance's close friend, Rodney Kyles Jr., brought father and son closer together. "It could have been Chance," Williams-Bennett says somberly. He gave Chance a one-year ultimatum: Make it as a rapper or go back to school.

Chance redoubled his efforts to build a grassroots following, visiting local high schools, recording at all hours of the night and handing out thousands of copies of #10Day on the streets of downtown Chicago. His manager, Pat Corcoran, signed on after watching Chance deliver one particularly intense performance at the Chicago streetwear store LDRS 1354. "It was scary," he says. "I didn't know [Chance] could perform that way."

Following #10Day's success, Chance sold out the 500-capacity Chicago club Lincoln Hall and toured nationally with Childish Gambino. This year, his upcoming two-night stand at the twice as large Metro, the historic venue that helped break Nirvana and Smashing Pumpkins, sold out in less than an hour.

Lighting a cigarette on the West Side rooftop, Chance pauses when asked where he currently lives. He has no permanent address – "I live around" – and Acid Rap is keeping things that way. This summer, he'll hit the road on a 23-date European tour with Macklemore and Ryan Lewis. "I'm conditioning my body to get used to it," he says. (A few minutes earlier, before coming upstairs to the roof, he casually pulled off a dozen reps on a perfect-pushup machine.) Chance hopes to bring a full band with him, but he'll settle for a trio.

"What about bringing a stand-up bass?" Corcoran suggests.

"Ah, that's it!" Chance exclaims, sitting up in his chair for the first time all afternoon. His eyes gleam with excitement. "Now that would be tight!"