Chance The Rapper has refused to cave to the pressures of followup albums and major label flirtation which is usually par for the course when it comes to emcees in a modern rap context.

Since he has forged his own unique path, his upcoming third major project, 3, which was created without any exterior weight, only promises to give the rising Chicago star more opportunities to be heard on a global scale.

Positioned alongside other young stars like Kendrick Lamar, A$AP Rocky and J. Cole, the public may have never known Chance by his descriptor, “The Rapper,” if it wasn’t for an encounter with the Chicago Police Department and administrators at his high school who gave the young creative a mandatory timeout from after running into a bit of legal trouble.

Many people’s first introduction to Chance The Rapper’s music came in the form of Acid Rap. The 2013 mixtape was met with near universal acclaim and actually ended up charting at No. 63 on Billboard’s Top R&B/Hip-Hop Albums chart after an opportunist began selling it on iTunes despite the project being free to the public.

It marked not only a shift in the ever-evolving paradigm that is the music business, but also signified that fans of Chance The Rapper were rabid enough to commit tangible dollars when acquiring projects for free – both by artist choice and illegal downloads – was the new cultural norm.

“This shows that there’s a strong appetite for Chance in the marketplace,” Chance’s manager Patrick Corcoran told Billboard. “How often does a bootleg hit a Billboard chart?”

Chance attended Jones College Prep in the Printer’s Row section of the Chicago Loop which is in the shadow of universities like Columbia College, Roosevelt University, Robert Morris University, DePaul’s loop campus, and the John Marshall law school.

“Jones is downtown,” Chance told Pitchfork. “It’s a really good school. My parents always wanted me to go to college.”

Austin Fassino/Sabrina Holder

In addition to being in close proximity to higher education and the hustle and bustle that comes with life and work in Chicago’s beating heart, Jones College Prep was also only a five-minute walk from the Harold Washington Library on South State Street which was home to YOUMedia – a “21st century teen learning space” – which began in 2009 and featured a 5,000-square-foot area that encouraged kids to dabble in aspects of music, graphic design, poetry and videography.

Chance was but one of many kids from the Chicagoland area who often used the facility to cultivate their creative streaks.

“It really started out contextualized for poets but then I remember Chance kept coming over and being like, ‘Hey, can we do rap over here too?'” Digital Youth Network’s Lead Mentor and Manager of Informal Learning Mike Hawkins recalled. “I knew he was more lyrical but I told him, ‘Well this is a poetry set, dude.’ But every week he would be there.”

“Production, software, piano lessons, music theory—I took all of them,” Chance remembered.

As Chance honed his craft, Hawkins was often close by to monitor his progress and cultivate the interests of a then freshman in high school.

“Very early on, even when he was a freshman, you could tell [Chance’s] level of literacy was way beyond that of the kids’ that I knew at that stage, especially in his rapping,” Hawkins told Chicagoist. “A lot of the stuff I was hearing was pretty basic at best. The only other kid I knew that was as good or, some said, better at the time was Vic Mensa from Kids These Days. I met him probably a year before I met Chance.”

Like other young artists, Chance found confidence in recording as a group rather than as a solo artist at first- forming “Instrumentality” alongside fellow rapper, J-emcee. The duo released two projects, the Back to School Pack EP (which can be streamed above) as well as Good Enough.

One of the highlights of this era of Chance The Rapper was his song, “Beddy Bye” which was created as part of a contest in which young musicians were encouraged to pen a song about Chicago. As the intro to the song points out, Chance believed he was moving to Washington, D.C. because his father served as a top aide for the newly elected President of the United States, Barack Obama.

“Chicago to me, is the kingdom of hearts,” he raps. “I dance through streets where a king once marched. It’s always where you finish and it’s never where you start. And I can’t outsmart when we move in the dark.”

Ultimately, Chance took home second prize in the contest, but Digital Youth Network’s Mike Hawkins thought he had created a certifiable classic.

“Now I’m going to go ahead and say on record it’s probably one of the best songs about Chicago that I’ve heard—and I’m putting it up there with the Kanyes, the Commons,” he says, “To me it was just up there with the classics, especially from a freshman.”

Several months later, Chance The Rapper found himself in legal hot water after a run-in with the Chicago Police Department outside of Jones College Prep.

“I had served this bitch the day before,” he remembered. “I was takin’ her to my crib and randomly she tapped out and was like, ‘I don’t even want to smoke anymore.’ So she gave me the blunt. And had she not given me that blunt, I wouldn’t have left it in my backpack. So when day I came to school and I had tweaked. I had this weed in my bag.”

Ultimately, Chance realized he had the illicit substance moments before he entered school, whirled around just in time, and ultimately retreated into a nearby alley to smoke up the evidence. It was here that the police intervened – choosing to also include the high school in the disciplinary matter which resulted in a 10-day suspension.

“I got suspended a lot, but senior year I got suspended for smoking weed right before spring break, which was sick because I had three weeks in a row off,” Chance remembered. “I wasn’t really good at high school or getting good grades and shit, and at that point, I wasn’t going to graduate. I was looking at my life and just like, ‘Who am I supposed to be?'”

The extended hiatus from high school gave Chance the opportunity to forge what would ultimately be his first solo project, 10 Day.

“I had already been making music for my whole high school life, and 10 Day, which took me a whole year to finish, was about working with a lot of different producers and learning all of the aspects about being a rapper, from shows, to recording, to studio etiquette, to marketing,” he said.

Alex Broadstock

Chicago hip-hop mainstay, Alex Fruchter, who co-owns indie label Closed Sessions and was Editor-in-Chief of Ruby Hornet – a Chicago-centric blog that gave Chance his first write up – recalled, “I was amazed at the cohesiveness of the project, and how structured each song was. Plus, he could really rap. And sing. And perform. And connect with his fans. And do all kinds of other things that no one else was doing at the time.”

Who knows if Chance The Rapper’s career trajectory would be the same would he have never been forced to sit back and reflect on his high school misstep. For most, the punishment would have been a chance to hibernate and indulge in video games and other distractions. But not for Chance. He put those 10 days to good use.

Words by Alec Banks
Features Editor

Alec Banks is a Los Angeles-based long-form writer with over a decade of experience covering fashion, music, sports, and culture.