Above: Chance at U.S. Cellular Field, home of his beloved White Sox Photo: Taylor Castle; Stylist: Whitney Middleton; Stylist Assistant: Keegan Greene; Groomer: Christina Artrip for Nika Vaughan Artists using Becca Cosmetics; Clothing: (hunting jacket and boots) ESQ Clothing; (T-shirt) WCSP/Jax and Debb; (jogger) Zanerobe/Jax and Debb

Chance the Rapper is running late. Not egregiously late, but late enough that there’s time to park on the bench in the lobby of his River West apartment building and guess the occupation of each resident exiting the elevators. Creative director. Hockey player. Recording engineer. It’s a nicer lobby than the average 22-year-old can afford—all windows and natural light—though not as lavish as you’d expect from a fast-rising hip-hop star.

Chance and his assistant, Colleen, arrive offering hugs and apologies. “Thanks for coming to my apartment,” he says. “I hope you don’t put that in. I know people always like to preface their stories with ‘As we sit on the top of Chance’s . . .’ ”


If you’re not familiar with Chance the Rapper, born Chancelor Bennett, here’s his abridged CV: Gifted, strong-willed son of a political operative pens rap lyrics while on a 10-day suspension from his selective-enrollment high school for smoking marijuana, then releases a mixtape in 2012. He follows it up a year later with an even better mixtape, the buoyant Acid Rap. Cue critical acclaim and popular demand (the album has been downloaded more than a million times), headlining slots at Pitchfork and Lollapalooza, guest spots on songs by artists as big and random as Madonna and Justin Bieber, and enthusiastic endorsements from the likes of Kanye West and Rahm Emanuel.

Chance will be back on tour in two weeks, drawing sell-out crowds of more than 3,000 (including celebrity fans such as Beyoncé and Jay Z). But today he’s sitting on a barstool in a common room on the apartment building’s top floor, wearing his standard attire: black sweatshirt, White Sox cap (he has three in constant rotation), and those inexplicably popular drop-crotch sweatpants. The bags under his eyes indicate he hasn’t gotten a lot of sleep. His girlfriend just had a baby girl two weeks before.


Fatherhood seems to suit Chance. “When you become a parent, you start loving diapers,” he says. “Going into it, I was like, ‘I’m not trying to change no shitty diapers.’ But when you leave the hospital, they tell you to count how many poops they take and how many pees. It’s like, ‘High five, another poop, we don’t have to go back to the hospital!’ ”

Having a child has changed him in more fundamental ways, too. “Anywhere past age 13—10 if you live in Chicago—you have a relationship with death as you’ve seen it depicted in media, or around you, if you’ve watched somebody die,” he says. “Until you have your own seed—and this is just me being religious—come from God and come to you . . .” He trails off, then picks up the thought again. “It’s a new understanding of life and of love.”

The baby is a main impetus for the new tour (fittingly called Family Matters); Chance is trying to squirrel away enough money for a house for his burgeoning clan. “I’m a patriarch now. I’ve got to go get the bread,” he jokes. There are other signs he’s maturing. He goes easier on the drugs and alcohol these days. And he’s highly cognizant of his growing influence (1.2 million Twitter followers) and wants to use it for good. “Being from the family I’m from—my great-grandmother marched with King—I have things that I have to do,” he says.

Those things include committing himself to the youth of this city. That means doing his part to curb violence (for the past two years, he has run, with his father and younger brother, a social media campaign, #SaveChicago, to encourage the city to go shooting-free over the typically murderous Memorial Day weekend), inspire up-and-coming talent (he founded and hosts an open-mike show in collaboration with the Harold Washington Library Center), provide some diversions (he helped mount a free teens-oriented music festival in June on Northerly Island that drew 3,300), and expose kids to the city’s cultural offerings (in July, he surprised Chicago Park District day campers by serving as their tour guide on field trips to the Adler Planetarium, Field Museum, and Shedd Aquarium).

In fact, after this interview, he’s headed to the Field to continue a conversation with the staff about making the museum’s Africa exhibit more relevant to black kids in Chicago. “It’s a little too all-encompassing for a whole continent,” he explains. Call him Chance the Curator.

Chance the Rapper performing at a concert
Headlining Pitchfork in July at Union Park Photo: Allison Ziemba

There was a time when Chance’s father envisioned a much different career for his son. The deputy chief of staff in Mayor Emanuel’s office, Ken Bennett has spent most of his life in the public sector. He worked for Harold Washington’s mayoral campaign in the ’80s and served as Obama’s deputy assistant during the president’s first year in office. His wife and Chance’s mother, Lisa, works as the director of community relations for the Illinois attorney general. Bennett had hoped that Chance would follow him into politics and tried to dissuade him from going into music.

Now, though, the elder Bennett recognizes the power Chance wields as a pop culture figure. “If you watch him and you listen to him, you realize he’s doing more to touch people in the capacity he’s in right now than he would be if he were a politician,” says Bennett. The community outreach ideas, he says, were “not something I pushed him to do at all. He makes great decisions.”

That wasn’t always the case. Chance and his brother, Taylor, grew up in West Chatham, a largely black middle-class neighborhood on the South Side, where Chance was a jokester in school and danced in talent shows. “We would always be getting into trouble for distracting the class,” says childhood friend Reese White, 22, who met Chance when they were in middle school. They were part of a crew called Save Money, now best known as a launch pad for rappers. At the time, though, it was a motley collection of teenage boys from the city’s selective-enrollment schools (Chance attended Jones College Prep) who would chill downtown and do, in Chance’s words, “illegal, fucked-up shit”: jumping CTA turnstiles, smoking weed, and getting into fights, mostly.

Father and son had always been close. Chance likens their relationship to Mufasa and Simba from The Lion King: “My dad would give me very stern talks while also telling me that I was a prince and I was gonna be a king and run this whole city.” But they endured a significant rift in 2011 when Chance announced his intention to forgo college to pursue music full-time. “One thing about Chance is that he’s extremely strong willed,” says his dad. “If there’s something that he believes he should be doing, he sticks to his guns.”

They gave each other the silent treatment for months—“even though we’d be standing five feet apart,” says Bennett—but that changed when Chance called his father from a hospital late one night in September 2011. His friend Rodney Kyles, 19, a fellow rapper and a sophomore at Roosevelt University, had just been stabbed to death in front of Chance during a fight outside a house party near DePaul University. “I realized I could have lost my son,” Bennett says. “That night, I woke my wife up and told her, ‘I can’t fight him anymore.’ ” He gave Chance his blessing.

Kyles’s death was a turning point for Chance, too. “Right after that I started being in the studio every day,” Chance told the Chicago Reader in 2013. “Didn’t really go out anymore, stopped doing all the drugs I used to do—it changed my whole life around. It was a very sobering event.” Says friend Malcolm London, 22, a poet and activist: “I saw him take his music 10 times more seriously, understanding just how futile life can be. He really started to hustle. You wouldn’t see him at parties anymore because he was busy working on his tape.”

Chance’s first album-length mixtape, 10 Day, garnered immediate notice when it dropped in the spring of 2012, thanks largely to the fan base he had cultivated through his open-mike performances at Harold Washington. He released the album for free and was planning to do the same with the follow-up. But the hype gave him second thoughts. “Chance actually came to me the day before Acid Rap came out and was like, ‘Man, we got to sell this,’ ” says his manager, Pat Corcoran, 25. “And I was like, hey, we set out to do a free project; I think we should stick to our guns and put it out for free.”


They did, and Acid Rap quickly drew the kind of national attention not usually seen with mixtapes. It made a number of year-end lists in 2013, ranking No. 5 (just below Beyoncé’s self-titled effort) in the Village Voice’s Pazz & Jop poll, which surveys the country’s leading music critics.

Acid Rap showcases Chance’s signature sound: nasally raps delivered over soul samples and juke beats, with guest verses from the likes of local motormouth legend Twista and Childish Gambino, actor Donald Glover’s rap alter ego. The album presents a vivid sonic tribute to Chance’s South Side upbringing. There’s an ode to his grandmother (“Cocoa Butter Kisses”), pointed social commentary (“Paranoia,” which features lines like “Down here it’s easier to find a gun than it is to find a fucking parking spot”), and clever wordplay (such as the double-entendre in “Smoke Again”: “Lean all on the square / That’s a fuckin’ rhombus”—for the uninitiated, he’s talking about smoking a cigarette, or “square,” soaked in cough syrup, or “lean”).

After Acid Rap, major record labels amped up their pursuit of him, but Chance has remained staunchly independent. “We took all the meetings, thinking, hey, maybe this will be for us,” says Corcoran. “So far, nothing has been.” Chance has a more righteous take: “It’s about making a statement that we’re in control as artists. That we make the decisions. There’s still that question when people meet you and see that you’re doing well: ‘Who are you signed to? Who put you on?’ Fuck that. I’m black, and I did it myself.”

His decision to remain unsigned led The Wall Street Journal to dub Chance “hip-hop’s most valuable free agent.” In an increasingly digitized music industry, where people can stream singles for pennies or download albums illegally, Chance’s model—growing his fan base with free access to his music and earning money by touring aggressively and hawking merchandise, such as branded T-shirts and baseball caps—makes economic sense. “Selling music doesn’t make that much money,” he explains. “On a touring guarantee, you’re going to make on one show about as much as a person made on their [album] yearlies—if they sold a million copies the first week and are still selling copies, which doesn’t even happen.”


Ask Chance if he’s famous, and he’ll give you a complicated answer: “Say I’m at a yogurt place and there are three people behind the desk. One person might think that I’m superfamous and start freaking out. The second person might be like, ‘I don’t know your music, but—funny story—you used to date my cousin,’ because it’s Chicago and it’s so small. And the third person might have never heard of me, doesn’t even really listen to hip-hop, but all three of them will probably ask for a picture.”

He smiles.

And how has the wider recognition changed his life?

Chance the Rapper and his father
Chance with his father, Ken Bennett, Mayor Emanuel’s deputy chief of staff, in 2014 Photo: Courtesy of Ken Bennett

“I’m me 24/7, so I go through things that some people might be like, ‘Wait, that still happens to you and you’re famous?’ I still have issues with the police. I still have places where I go and get mistreated. It makes me a little bit more paranoid, a little bit more cautious of things that I do.”

Friends insist he’s the same goofy, film-obsessed, churchgoing guy he’s always been. “He’s done a great job staying true to himself,” says White. “He’s not a flashy type of rapper, making videos about riding in expensive cars.” (Exhibit A: Chance’s music video for the Donnie Trumpet collaboration “Sunday Candy” takes the form of kids putting on a school play.)

“Fame hasn’t really thrown him off a lot, because of his experience,” adds Corcoran, referring to Chance’s background as the son of someone with connections at the highest levels. (Corcoran became Chance’s manager in 2012 after surviving a barrage of questions from Bennett about how he planned to promote his son.) “Chance has been in rooms with the president before, he’s been in rooms with politicians. He knows it comes with the gig.”

Of course, with fame comes power—the ability to call shots in ways Chance had only dreamed of before. “Since I put out 10 Day, I’ve wanted to sit down in an office at Apple and be like, ‘Yo, you need to put out a free album that’s my album and put it in the iTunes Store,’ ” he says. “People were like, ‘That would never happen.’ ”

But then, last year, it did. An Apple executive reached out to Corcoran in the fall of 2014 about doing a project with Chance. Chance and his band, the Social Experiment, were tinkering with Surf, their latest project, led by bandmate Nico Segal, a.k.a. Donnie Trumpet. Over a series of meetings in California, Chance says, “I got to sit down at Apple with a cracked iPhone”—he holds it up for emphasis—“and they said, ‘Yes, whatever you say, Chance, let’s go.’ ” Surf was released, for free, on iTunes in May and, according to Chance, had more than 600,000 downloads in its first week.

Chance the Rapper serving as a tour guide at the Shedd for day campers
Chance serving as a tour guide at the Shedd for day campers from Fuller Park in July. Photo: Courtesy of Museums in the Park

Chance the Rapper is about to give a motivational speech. He is very good at motivational speeches. He dispenses them frequently during his live performances. Sometimes they’re simple commands: “Jump! Stomp! Clap!” Other times they are treatises, requests for ownership. “This is your show. There’s no streaming here, it’s just us,” he told a Pitchfork audience in July. The speeches are a little corny, yes, but well meaning and sincere.

The setting tonight is a bit different. Since February, Chance and a group of his friends—artists, rappers, and activists—have put on Open Mike, a free semiregular talent show that any high school student with a valid ID can participate in or attend. The group holds the shows in honor of their friend Mike Hawkins, a poet who died last December at age 38. Affectionately known as Brother Mike, he served as a father figure and mentor to many artistically inclined teens and produced Lyricist Loft, the weekly open-mike event at Harold Washington where Chance spat his first rhymes. (Search YouTube for “YOUmedia Summer Soul Session Chance” and watch him bashfully rap the words that would become 10 Day’s “Nostalgia.”)

“Brother Mike was just invested,” Chance will later explain. “He wanted to know what I was writing and what I was working on. He was the kind of person to tell me not to perform the same poem twice.”

So on this Monday night in September, Chance is paying it forward. He’s standing onstage in front of four rows of attentive teenagers at Harold Washington’s Cindy Pritzker Auditorium, sporting camo pants and a white T-shirt emblazed with the words “Open Mike.”


After some earnest spoken word and profane rap from students (despite the staff’s best efforts to keep the event PG) comes the part of the show when an established artist performs. In the past, Kanye West, Vic Mensa, and comedian Hannibal Buress have done sets. But appearances by tonight’s scheduled pros—the singer Jeremih and rapper Lupe Fiasco—have fallen through, so Chance is about to break his own rule.

“Since we first started doing the open mikes, I’ve tried to make the point not to have me or the other staff members perform,” he tells the crowd of about 50. “We didn’t want it to feel like there was a time for you to perform and then a time for us to perform. I know how hard it is to come up onstage and say a poem that only you know or do a dance that only you’ve seen before. So I want to show you that I’m just as vulnerable as you guys. I want to show some pieces I’m working on. I’m nervous.”

The teens laugh and murmur in disbelief.

He then proceeds to perform two songs a cappella. The first is from his forthcoming album. The second is the recently released “Israel (Sparring),” a tender number that harks back to his own open-mike days with its sinuously rhymed lyrics.

Sparring is training / Chain snatching the slaves / But a rap song is a match in a cave / Dim lit, wet wick, wicked wrath in its way / I go violent—

“Wait, fuck, I messed it up.”

He starts over.

Fuck the pharaohs and Pharisees, Moses is back / I don’t need to see a sphinx to know they noses was black.

He forgets the lyrics again midway through. But no matter. This time the kids feed the words to him.