Holed up at a recording studio in Chicago’s Near North Side, Chancelor Bennett — the local phenomenon known as Chance the Rapper — is in wise-old-man mode. Chance, 23, holds a cigarette aloft in one hand, a pen in the other, his narrow shoulders hunched over a notebook. It’s late on a Saturday night in July, and he has been working for hours, writing a song he will perform as a tribute to Muhammad Ali during the finale of the ESPY Awards, to be held in Los Angeles in a couple of days. “When I write, I work off of a theme, an emotion, a narrative — thinking of it and then expounding on it,” says Chance. “I was trying to rap with mad boxing metaphors, being very literal. It was cheesy.”

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So instead Chance imagines the song as a letter written by his mother, Lisa, to Ali. As a girl on the South Side, she lived near the boxing legend, and she often has recounted how she braved the walk to his front door only to discover that he was out of town. But the letter isn’t right either. Chance decides the song needs to be “more sort of liturgical” after his thoughts turn to his father, Ken, a political operative who has been a deputy assistant to President Obama and more recently Chicago Mayor Rahm Emanuel’s deputy chief of staff. “I see so much of my dad in Ali,” says Chance. “Their voices, the physicality of them, their vulnerability.” Chance’s engineer Jeff Lane has been waiting for five hours to record the completed verses. He nods admiringly at Chance grinding inside the sound booth: “You think Rihanna does this?”

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If it seems odd that a rapper who calls himself Lil Chano From 79th would be chosen to eulogize THE GREATEST, on primetime network TV, in front of the world’s reigning celebrity athletes, then consider how Chance has become an iconoclast in his own right. He emerged as 2016’s most highly praised rapper, an heir to Kanye West (his mentor) and Kendrick Lamar (who in a recent issue of this magazine named Chance as a favorite MC), all without signing a record deal or even charging money for a single song. He performed on Saturday Night Live as the show’s first-ever unsigned musical guest in December 2015, then returned to the show two months later with West, delivering a guest verse on the latter’s “Ultralight Beam” that was hailed as a poetic knockout. (It went, in part, “You can feel the lyrics, the spirit coming in Braille/Tubman of the underground, come and follow the trail.”)

In May, Chance and his handpicked, mainly Chicago-based team — who put out his two earlier mixtapes as free downloads — partnered with Apple Music to release his third album, Coloring Book, as an exclusive two-week stream. (Apple put up an undisclosed sum in exchange for the exclusivity.) Coloring Book not only became the first streaming-only album to chart on the Billboard 200, it opened in the top 10 and — now that the Grammy Awards have rewritten their rules to make streaming-only albums and songs eligible for awards — is hotly tipped for a nomination. Coloring Book also proved to be Chance’s most adventurous work as an artist, with a bold turn to gospel and soul-searching lyrics to match. “This guy is the future,” says Carl Chery, head of hip-hop/R&B programming at Apple Music. “He’s the most exciting hip-hop artist of the last five years.”

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Days after he delivered the Ali homage at the ESPYs, the Olympic committee asked Chance to compose an original number for this summer’s games in Rio de Janeiro. It’s hard to imagine any other young rapper, focused on the tangled particulars of his block, who possesses the moral authority to represent the country or the world in song. But Chance’s music is uniquely inspiring, sonically and socially inviting, and blissfully religious. His hip-hop scene has the feel of a big, carousing collaboration, with him and his childhood friends living out a cross between a Christian High School Musical and a Judd Apatow film, if Seth Rogen and his stoner crew were prodigies from inner-city Chicago. It’s a balancing act he pulls off seemingly without ego or pretense. “He’s the youngest old man I know,” says Hebru Brantley, the Chicago muralist and Chance collaborator. “To be so young and so wise.”

Chance named his first album, from 2012, 10 Day, because when he recorded it he was on a 10-day suspension from his test-in public high school after getting caught with weed. “It has a lot of school references, maybe too many,” he now says, laughing. The album captures the life of a black middle-class teenager who loves his family, his fellow musicians and his troubled city. It’s a complicated portrait, both juvenile and profound. There’s sex and drugs and Spanish class as well as the looming threat of violence: “Round here we lose best friends like every week/I like to think we playin’ a long game of hide and go seek.” Chance isn’t a storyteller like Eminem, and he doesn’t conjure atmosphere as a disturbance the way Lamar does. He’s more of a collagist, bringing together a series of images that are indelible for their specificity and intimacy. “For young people on the city’s South or West Side, there’s nothing coming from government, from our school system that’s bolstering the kind of pride that comes out in Chance’s work,” says singer Jamila Woods, who has worked with Chance on his albums as well as on her own newly released Heavn.

Chance developed his craft at a downtown after-school program called YOUmedia and at an open-mic venue called Young Chicago Authors. These spaces exposed him, in hyper-segregated Chicago, to music heads traveling from every corner of the city. He hooked up with the members of Kids These Days, a rock-rap-jazz band that included Nico Segal, who performs with Chance as Donnie Trumpet, and the rapper Vic Mensa. “We all became friends, and that collaborative process has been the blueprint for our careers,” says Segal. Chance seems to view all his musical counterparts with the same familial spirit, eschewing beefs and rap battles. “I never really liked the idea of rap being a competitive thing. It’s not. I can’t gain anything off of anyone else not succeeding,” he says.

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Chance’s little brother Taylor, 20, also raps, and Chance appears on his 2015 debut, Broad Shoulders. Chance’s mother works for the Illinois attorney general’s office, and his father, who left the mayor’s office this summer, is now an executive with Chicago’s tourism bureau. During the past couple of years, Chance has seen Chicago’s problems up close — “My dad is getting the call every morning, updates on how many kids got shot the day before” — and his views on issues like police brutality are nuanced. He chides Emanuel for how he responded to the killing of Laquan McDonald, who was shot 16 times by a Chicago police officer in 2014. “In a time of crisis he tried to be strategic, and he should have been more compassionate,” says Chance. More generally, he adds, “There’s a larger conversation we need to have about the role of police officers, their relationship to the people as enemy or executioner, when they’re not supposed to be either. There’s also not enough pressure on internal organizations that are supposed to police the police and on judges in the justice system who are supposed to make reasonable decisions.”

At 16, with his dad following other Chicago politicos to Washington, D.C., Chance met the newly elected Obama, and this year, along with a dozen other prominent musicians, he returned to the White House to talk with him about the anti-violence initiative My Brother’s Keeper. (“I’m more confident than ever,” Chance tweeted after the meeting.) In Chicago, he has used his father’s connections and political know-how to start an open-mic for teens, distribute a combination jacket-sleeping-bag to the homeless, sponsor events at the Field Museum and fund the church camp he attended as a child.

“He’s just one of those humanitarian-type of individuals,” says Chicago singer Jeremih a couple of days after Chance joined him onstage at the Pitchfork Music Festival. “There’s not a record he can’t hop on, a genre of music he can’t relate to. I don’t know too many people who could go on Jimmy Fallon one night and go to a peace rally the next day.”

Chance shopped 10 Day to most of the major and a few indie labels, expecting to sign a record deal. But while he considered offers, he sold out a 500-seat venue in Chicago and was invited on tour with Childish Gambino. He figured a decision could wait. He knew he wouldn’t need a label to produce and distribute his second album, Acid Rap (“I recorded it while on acid,” he explains simply). The month he made the mixtape available for free, he went on tour opening for Mac Miller in “midsize rooms outside the Midwest.” “The kids knew all the words to my songs,” says Chance. By then he had connected with his manager, Pat Corcoran, 26, a white North Sider with a hang-loose vibe who had been setting up shows for Kids These Days while at DePaul University. “We discovered going with a label wasn’t for us,” says Corcoran.

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Chance has earned money not from 99-cent downloads but from tours, merchandise, meet-and-greets and his deals with Apple and other companies — like Bud Light and Citibank, sponsors of his upcoming Magnificent Coloring Day festival — eager to reach his many young, savvy fans. (Coloring Book also expanded to Spotify and other streaming services after the Apple Music exclusive.) “It’s not about the music being free. It’s about how it is displayed and made accessible and about artistic power,” explains Chance. “It was always about the artist-to-fan relationship.” On a recent Saturday night, Chance tweeted to his 1.9 million followers that he would be making an announcement the following morning. It turned out to be a surprise show at a Chicago club, and on Sunday he updated fans on where they could buy pairs of tickets-(including at Lou Malnati’s Pizzeria and a Harold’s Chicken). The treasure hunt ended at 2 p.m., when the venue sold out. “This is exactly why I keep my @chancetherapper Twitter notifications on,” one fan tweeted with a photo of his tickets.

The Magnificent Coloring Day festival, which Chance will headline as part of his current tour, showcases his ambition and hometown love, with Alicia Keys, John Legend, Lil Wayne, Skrillex, Young Thug and 2 Chainz joining him at U.S. Cellular Field, home of baseball’s White Sox, for whom he designed a line of specialty caps. The festival has broken the ballpark’s attendance record, selling more than 50,000 tickets. “It’s bigger than me f—ing with the Sox and bigger than me being a rapper,” says Chance of organizing the festival, noting that it will create jobs and attract tourist dollars. And, he says, “I think the city needs some happy moments.”

Around 2:30 a.m., at the Near North Side studio, Chance is finally ready to start recording. He stands at the mic, the room dark but for a flickering screen showing Ali fights. (“I’m a method engineer,” says Lane.) Chance shuts his eyes, listening to the opening bars of a traipsing piano and the horn that follows. Then he sings, “Steady hold, I’ve grown weary and old.” After Drake, every rapper wants to be a singer, and Chance uses the rough physicality of his voice to convey emotion, landing hard on Ali’s famous superlatives — “Ain’t no one prettier/Ain’t no one wiser/Ain’t no one better! better! better!” The song, says Chance, is about spiritual redemption, about Ali finding God, with a hook made lush by Woods: “I was a rock/I was a rock and roller/But now I’m just a rock.”

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The Ali tribute, like a lot of music that Chance has been writing lately, veers into gospel. On Coloring Book, he samples praise music and employs worship star Kirk Franklin. Chance attends the South Side’s Covenant Faith Church of God, meets with his pastor and is conversant enough with scripture to pack his songs with surprising Biblical allusions. “Sunday Candy,” from the Donnie Trumpet & The Social Experiment album Surf, is an exuberant hymn to Chance’s grandmother. The tune is a romp, but the pleasures described are that of his family’s black church. “You look so good with that hat on, had to match with the shoes/Came and dressed in the satin, I came and sat in your pew.”

The Ali song also delivers a personal punch, with Chance as the prodigal “roller.” He moved to Los Angeles in 2014, after the success of Acid Rap, and developed what he describes as a bad Xanax habit. “I don’t want to present it as a Behind the Music thing,” he jokes. “I looked up and months had passed, and I hadn’t made enough music.” He also found that he belonged back in Chicago: “I missed a lot of weddings and funerals.”

At the studio, Chance’s girlfriend Kirsten, whom he has known since childhood, shows up. They had a daughter in 2015 — tonight she’s with Kirsten’s mother — and the three now live together. Chance takes a breather, and the couple enacts a scene straight out of his song “Smoke Break” — she sits sidesaddle in his lap, pulls on a blunt and then holds it to his lips. “I understand how black women are represented in rap music, how being a baby mama is perceived,” he says. “My girlfriend and I are very conscious of how many people in our situation don’t think it can work out, when it can.” He also has become less open with his drug and cigarette use. “Kids would tell me they tried acid for the first time listening to Acid Rap, asking me if I wanted some. I realized the responsibility of being a popular artist.”

Settled again in Chicago, Chance tattooed a directive above his heart: “Get back to work,” written backward so it would face him in the mirror. Chance wrote parts of five songs on West’s The Life of Pablo, observing how his idol (“I’m literally Kanye’s biggest fan”) rented out an entire studio and acted as ringmaster, simultaneously directing different rooms populated by writers, engineers, producers, seamstresses, even magicians. “I watched him knock out six, seven songs that way,” says Chance. “I stole that.” To finish Coloring Book, he rented out the Chicago studio and with his team slept there overnight on inflatable mattresses.

At the Taste of Chicago, in July, Chance performs with Donnie Trumpet & The Social Experiment. With his thin frame and his White Sox cap pulled low, Chance is a sudden pinwheel of ecstatic motion. He is joined by his closest friends, old and new. The typical crowded rap stage displays strength in numbers, but Chance means to evoke a choir. “It’s about group work, harmonic collaboration,” he says. “The whole project is very loving, and shouting it in a group is powerful.” The fans sing along on “No Problem,” a joyous threat to any executive who interferes with Chance’s independence.

But the set is more sacred than profane. They end with “Sunday Candy,” and the concert takes on the cast of a revivalist meeting. Palms are raised skyward, fans shouting every word. Chance isn’t merely using gospel, he’s doing its work. The people in Grant Park seem transported, ready to follow wherever Lil Chano From 79th takes them next.

This article originally appeared in the Aug. 20 issue of Billboard.