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.

No, you're not tripping. The newest rap star out of Chicago is an energetic former Obama volunteer with a taste for the psychedelic. Take a ride with Chance The Rapper and set your mind free.

This feature appears in Complex's October/November 2013 issue.

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.

With the arrival of Acid Rap, though, his music was shot through with something darker. There’s a morbidity underlining even his nerdier punch lines. On “Smoke Again,” Chance raps about lean-soaked cigarettes: “Lean all on the square, that’s a fuckin’ rhombus.” During a break in the action in Detroit, Chance says he has since kicked the habit. “There was a point where I just did not care about my body. I just felt indestructible. I was smoking mad lean squares,” he explains. “That was really bad for me, so I stopped.”

The buzz and attention generated by Acid Rap says a lot about the current state of hip-hop. Listeners are looking for artists who can challenge conventional wisdom about hip-hop archetypes and the younger generation.

Since Acid Rap’s lead single, “Juice,” dropped in the spring, there has been a major-label feeding frenzy, with rampant rumors of multimillion-dollar offers. Anyone who hadn’t been swayed by “Juice” fell for the follow-up, “Acid Rain,” which Chance’s manager, Pat Corcoran, says attracted the attention of Paul Rosenberg and Shady Records. The song makes an explicit, heartfelt reference to the fatal stabbing of Chance’s friend Rodney Kyles Jr. during a fight in Chicago. Chance witnessed it firsthand, as he explains on the track: “My big homie died young, just turned older than him/I seen it happen, I seen it happen, I see it always/He still be screamin’ I see his demons in empty hallways.” In the next line, Chance implies that this trauma may have led to his LSD use: “I trip to make the fall shorter/Fall quarter was just a tall order.”

The buzz and attention generated by Acid Rap says a lot about the current state of hip-hop. Listeners are looking for artists who can challenge conventional wisdom about hip-hop archetypes and the younger generation. The success of Kendrick Lamar, who rose from mixtape sensation to best-rapper-alive contender, has helped fuel the excitement around Chance. His music reflects a diverse set influences, incorporating Eminem’s delivery, the joie de vivre of Lil Wayne, and the technical innovations of California’s underground heroes Freestyle Fellowship. “When I found Freestyle Fellowship, I started getting into the construction of rap,” Chance says. “You get better at it the more you do it, you figure out the science and the math behind it. You can construct shit like it’s a problem instead of listening to the song. But with Em it was just so fucking sporadic and energetic. It was a big part of me figuring out my sound.” Looming above them all, of course, is Chance’s fellow Chicago native Kanye West, the forefather of a generation of artists interested in complicating rapper archetypes.

As everyone notes the first time they hear Chance rap, he sounds a world away from the music being made by drill rappers like Chief Keef and Lil Durk, even though those MCs grew up down the street from where Chance was raised, in the Chatham neighborhood on Chicago’s South Side. When the drill scene first broke into the mainstream in 2012, part of the reason it resonated was because it seemed like these were voices that hadn’t been heard before. Since then, the pendulum has swung so far that for some, the city’s hip-hop scene—and even the city itself—has been reduced to a violent caricature. Now, a new voice is confounding perceptions about Chicago rap.

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.”

Back outside the Fillmore, Pat The Manager and Danny decide to check into a hotel and park the RV while the rest of the team goes out. On the way to Sweetwater Tavern, a Detroit wing spot, the group attracts fans who found their way to the artist area after the show: girls that Oreo is chasing, guys who accompanied them, and a few random kids in their late teens or early 20s. Sweetwater is the kind of restaurant that plays Young Jeezy at full blast on a Tuesday evening. Two long tables are pushed together and everyone orders food. Chance seems more interested in catching up with his old friends than making new ones. After everyone’s eaten, he makes his move, leaving the hangers-on behind.

Someone has obtained cards for free entrance to The Office, a strip club in downtown Detroit. Now reduced to a core group—Chance, keyboardist Peter, bearded Nate, school homie Justin, and two girls Chance knows from Chicago—the crew enters the sleepy club. It’s half empty, a dark room with one guy sitting at a table, literally asleep. No one recognizes Chance, aside from one of the club’s employees, a man with an expensive-looking chain hanging around his neck. But the arrival of a group of younger people stirs the strippers to life, as they make their way past the jaded regulars. One of the women latches onto Peter, while another, who goes by the name Cash and has the word “money” tattooed on her right breast, gives Chance a lap dance. Nate heads to the ATM, only to find out that the fee is $10; he decides against making a withdrawal.

Around $60 in drinks and tips later and it’s 2 a.m.: closing time. Unfulfilled, Chance and company add Deja Vu, a strip club with later hours, to the itinerary. Piling into Chance’s friend’s car—the group is slightly too large for the number of available seats—they’re off again, driving eight miles outside of downtown while blasting Rich Homie Quan’s “Type of Way,” the unofficial anthem of this leg of the tour. Upon arrival, the group discovers that the strip club has an $11 cover. Unwilling to take on that expense, everyone stuffs back into the car, and hits the highway back to the hotel.

“[My dad] 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 seriously.”

The following morning, after airing out the RV, the crew begins the three-hour drive around Lake Erie from Detroit to Cleveland for another show that evening. Sitting in the backseat, Chance shifts the convo to a new hobby he’s taken up: skydiving. He talks about jumping out of an airplane thousands of feet in the air, and how, after pulling the cord, he goes from hurtling at terminal velocity to floating in a kind of perfect serenity. Pat The Manager isn’t quite as excited about this new activity as Chance is. Up in the plane his first time, Pat backed down. “I was just like—I don’t have to do this,” he laughs. But Chance loves the thrill.

On the road, some folks snooze, while Chance passes time watching Eternal Sunshine of the Spotless Mind on a laptop with headphones. (He loves the score.) Once the crew arrives at Cleveland’s House of Blues, Peter sets up his production equipment and a laptop in the dressing room. He’s putting together a loop with a vague ’80s R&B vibe, claiming Bobby Caldwell as inspiration. Chance begins writing to the beat, reciting a singsong melody and filling in lyrics.

Hours later, Chance trots out on the House of Blues stage. Compared to his reception in Detroit, the outpouring of energy from the fans in Cleveland feels significantly higher. (Pat theorizes that the audience at the Cleveland show is demographically closer to Chicago—meaning, less suburban than the crowd in Detroit.) During the outro of his set, prior to dropping the “Versace” remix, Chance throws in a fan favorite from 10 Day, “Fuck You Tahm Bout,” which uses the instrumental to Waka Flocka’s “Fuck Dis Industry,” an appropriate selection given Chance’s ambivalent approach to the rap business. Sometimes he weighs his interest in movies. He’d like to direct, he says, or maybe go to college instead of rapping. But then he comes to his senses and realizes that there’s nothing he’d rather be doing right now.

Most of the Cleveland crowd seems to have come on board with Acid Rap. They’re not too familiar with the older song. Chance’s brief performance of the track feels like a measure of his confidence in that moment. Afterward he bursts into the dressing room fresh from the stage, shirtless, and starts freestyling over a beat that Peter is playing on a loop, free-associating on topics ranging from his social media feedback to his DJ’s gymnastic history: “A comment on my Instagram said I was dressed classy/I said ‘Hey, why don’t I drop another classic?/Why don’t I get high and record over a classic?’/With my nigga who do backflips.”

After the show, one of Nate’s friends meets up with the crew, and they pile into her car for a run to a near-empty mall for some Taco Bell. In the parking lot, they lean against the car, eating chalupas while Rich Homie Quan plays in the background. Hunger sated, they return to downtown Cleveland, park the car, and start walking down the street. Suddenly Chance takes a flying leap and lands on the air vents embedded in the sidewalk. “Every time I get over one of those, I jump as hard as I can on that shit,” he says matter-of-factly. “Just on some, what if I died, falling through a city grate? Guess that’s just the way I’m supposed to die.” Reckless youth? Sure. Some might call this taking chances. Some would say Chance is taking off.

ADDITIONAL CREDITS: (STYLING) Matthew Henson. (GROOMING) Katelyn Simkins. (CLOTHING) OPENING SPREAD: Sweatshirt by Won Hundred / Pants by Zanerobe / Hat throughout by Society Original Products / Bracelet Chance's own. FOLLOWING SPREAD: Jacket by Surface to Air / T-shirt Chance's own. THIS SPREAD: Hoodie by Christopher Kane / Jeans by Won Hundred /Sneakers and socks Chance's own.