After running through his usual set list at the Fillmore, Chance ends his show the same way he has all tour: DJ Oreo drops Chicago drill rapper Katie Got Bandz’s dubstep-style “In The Field” while Chance sprays the crowd—who are, by this point, thoroughly open—with a Super Soaker. As he pumps up the audience for the headliners, Oreo finishes with Migos’ Drake-featuring “Versace” remix while Chance bounds off the stage.

Chance takes every aspect of his live show very seriously. Ever since he was a kid, he analyzed Michael Jackson’s concert performances, particularly the Live in Bucharest: The Dangerous Tour DVD. “If I hadn’t gotten that DVD, I wouldn’t be a live performer,” he says. “That was what I studied, the dancing on stage and incorporation of the crowd and the leg drops and the emotion of the set. Making it a story so that people stay with you the whole time—so you’re not just playing random songs.”

Chance’s dressing room at the Fillmore sits on the third floor, above Earl Sweatshirt’s, which is above Mac Miller’s. Inside, a table is scattered with junk food and fruit. A box of Coronas sits in the mini fridge. Chance and his small entourage—his manager, Pat and a mix of friends and musicians—all get along well with Mac and Earl, but they spend the most time with fellow opening act The Internet, the funk band led by Odd Future’s DJ Syd tha Kid. Conversation jumps around, as members rotate in and out of the room to smoke cigarettes and watch Earl, then Mac, from the side of the stage. A recurring topic of conversation in the dressing room is the difference between L.A.—where members of The Internet reside—and Chicago. Chance explains how he navigates the neighborhoods. “Some blocks you know you don’t go to,” he says. Someone claims that Chicago’s West Side has no trees or grass, which Oreo, who is from there, strenuously denies. The conversation inevitably leads to a discussion of the best Chicago pizza. Chance’s favorite is Lou Malnati’s, which, in a room full of hip-hop artists, is immediately misheard as “illuminati.” These are Chance’s new rules of rap stardom—he cares about pizza, not secret societies.

Touring is equal parts fun and educational for Chance; every performance functions as a way of introducing himself to a new audience, as well as an opportunity to learn from his peers. During Mac Miller’s set, the Pittsburgh rapper asks the audience to sit down, then jump up when the music drops. Chance observes that the crowd near the front of the stage is too tightly packed to sit, so they end up milling around, confused. “He should tell them to a take a step back first,” says Chance, making a mental note. All of this experience will serve him well as he continues his tour schedule. Chance has fifteen more shows to play in the next two and half weeks, including a headlining stage at Lollapalooza. After that it’s Europe, opening for Macklemore, and then a gig opening for Kendrick Lamar, and later, Eminem.

 

“I was a mad impressionable kid, and every skit from The College Dropout was telling me how I didn’t need school. And I think that had a very big impact on how I treated it.”

 

After the Fillmore show ends, Chance steps outside for a smoke. It’s still light out, and a group of fans loiters next to the artists’ parked touring vehicles. Earl and Mac Miller have twin buses, long and sleek. Chance and his entourage—new to the game, unsigned, traveling light—ride in a used camping RV that he purchased to save money on a bus rental. The onboard bathroom isn’t functional. Some nights, the group crashes in the RV; other times, they stop in hotels and share rooms.

Recently, the RV crew has swelled to six members, with the newest additions being two of Chance’s producers: beatmaker Peter Cottontale, an Afroed keyboardist, and Nate Fox, who is white, bearded, and small-statured. Nate produced several tracks on Acid Rap; he and Peter are here so that Chance can begin recording new material on the road.

Other tour mates include Danny, the friendly, blunt-rolling driver, and Justin, one of Chance’s best friends since grade school (and a cohort in their early high school hip-hop group, Instrumentality). Justin is on summer break from a college in upstate New York, and isn’t involved in the music industry. Quiet and introverted, Justin seems to be Chance’s closest confidant. He’s the only one on the trip without a clear job to do.

At the other end of the personality spectrum is Oreo, Chance’s energetic DJ and hype man. Perpetually clad in Ralph Lauren pajama pants and a pair of Jordans, Oreo wears his hair up in braids and is often described as looking like Wale (during a freestyle session in the RV, he jokes knowingly about this comparison). As a kid, Oreo aspired to become an Olympic gymnast. He was part of Chicago’s renowned Jesse White Tumbling Team, an acrobatic squad of athletically gifted youth that performs nationwide. But by his early teens, dreams of music took over. While warming up the crowd between sets at a King Louie concert last October, Oreo caught the attention of Chance, who had opened the show. Months later, the two were officially a team.

Among Chance’s entourage, one guy calls most of the shots: Pat The Manager (to go with “Chance The Rapper”). Pat is a husky, blond 21-year-old bro with an affable, easygoing personality. He’s the point person for Chance’s business affairs, which these days include fielding calls from guys like Lyor Cohen and Nigil Mack, the A&R who signed Kid Cudi, as well as handling tour merchandise and performance details. He’s also the dude who walks onstage at the end of each set to hand Chance his Super Soaker.

Pat beat out a host of other candidates, including one-time Kanye West manager John Monopoly, to land his job. Though he admits that he and Chance are still learning how to build on their current success, he’s confident about the way they’ve handled the increased attention that followed Acid Rap. “We were ready for it. We handled it,” he says. “I always say, ‘The good get lucky.’” Pat and Chance believe that the rapper’s value is still rising, which is why they are patiently fielding offers and refusing to sell low. Hence, traveling cross-country in a used RV.

The man who looms largest in Chance’s life and career, his father, is not on tour. But it’s Mr. Bennett’s voice that opens the final cut on Acid Rap, “Everything’s Good (Good Ass Outro).” “I had just started writing,” Chance explains, “and my pops always calls me randomly. Every time he calls me he starts saying some deep, super-inspirational shit about how much he loves me—every day, or at least every other day. So I was like, ‘I’m in the studio. I should be recording this.’ That conversation was going on for like five minutes before I recorded it.”

Things weren’t always so lovey-dovey between father and son. Prior to his success, Chance describes their relationship as strained, if not estranged. In a family that stressed the importance of education, Chance didn’t seem to care about school. He lays part of the blame for this attitude on Kanye West: “I was a mad impressionable kid, and every skit from The College Dropout was telling me how I didn’t need school. And I think that had a very big impact on how I treated it.” The one assignment he remembers turning in during senior year was an essay on why he didn’t want to go to college. The 10-day suspension for smoking weed didn’t help matters with his father. “I was like his bad son,” says Chance, whose younger brother, Taylor, is also a budding rapper. “At one point [my father] was like, ‘I might have to kill this nigga. He is too bad. I put this nigga in the world….’” Chance trails off, leaving the rest to the imagination. “He used to say that. Only way more violently.” Chance told the Chicago Reader that he once let three months pass without speaking to his father. The silence was broken when Chance’s friend Rodney was killed in August of 2011. “He picked me up from the hospital. It was a really crazy situation that we went through,” says Chance. “And from then, we just valued each other a lot more. He really started taking my music shit seriously.”

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