Greenroom 01 Cover Story: Chance The Rapper

words by Alex Fruchter

photography by Austin Fassino


This is a story about before and after. This is a story about how much can change in a year and a half. It’s a story about a rising youth movement inside of a city known for being tough on its young. It’s a story about new models and the digital age, how good old-fashioned hard work still has a place in our modern world. This is a story about Chicago’s Chance The Rapper. This is a story about before and after.

Chance The Rapper’s story starts before he cursed live on MTV, or called out the media on ignoring Chicago’s epidemic of youth violence while exploiting the music of him and his peers. This is before Chance sold out back-to-back nights at Chicago’s storied Metro Music Hall. This is before he was skipping meetings with powerful record executives and making songs with Skrillex. This was before Chance The Rapper crisscrossed the United States with Mac Miller or headlined a stage at Lollapalooza, and before Chance was praised by Q-Tip and J. Cole. This story starts at a time when Chance was Chicago’s underground hip-hop secret, way before he was asked to be the new face of a revitalized MySpace, now backed by Justin Timberlake.

The dynamic is pretty wild, and probably hard for an outsider to fathom. I know I’m amazed, and I’ve seen everything first hand. I grew up on the southside of Chicago in a neighborhood known as Hyde Park. It’s a neighborhood full of diversity, one that emphasizes the idea that it’s cool to be smart (both in the street and book sense of the word). After graduating from Indiana University in 2004, I moved back to Chicago and taught elementary school in Englewood, a neighborhood just east of my own, but truly a different world. After the classroom, I dove head first into my first love, hip-hop, and have been entrenched in the scene ever since as a writer, DJ, and now president of the independent hip-hop label, Closed Sessions.

At only 20 years old, Chance The Rapper (Chancelor Bennett) is, to put it simply, on top of the world - and it’s hard to remember a time when almost nobody knew his name. It was only last summer I walked through multiple record label offices in New York, fielding questions like “who should we be watching out of Chicago right now?” When I would answer “this kid Chance The Rapper,” all that came were blank stares and “okay, buddy” nods.

But as the weather grew colder, Chance began to catch everyone’s attention. By March 2013, he officially declared that he had “The Juice”, playfully dancing his way through Times Square in the video [directed by Austin Vesely] that would heighten expectations for his sophomore mixtape, Acid Rap. It made Chance one of the most coveted artists to watch at South By Southwest, a music festival built upon the allure of finding the next “big thing”. Following SXSW, there was talk around Chicago’s hip-hop circle that Chance had stepped directly off a showcase stage and into a meeting with Paul Rosenberg, Eminem’s manager and business partner. Funny thing was, nobody doubted it for a second. I certainly didn’t. Chance is that good.

In July 2013, popular blogger Karen Civil tweeted another rumor. “Streets are saying Chance The Rapper signed his deal for $5 million,” she wrote. That one was a little less believable, but not because of the high dollar amount. Everyone knew Chance could sign a ridiculously lucrative contract - the shocking part of the tweet was its timing. Fiercely independent and protective of his creative control, Chance is confident in telling any major label to wait and see. In June, he collectively told everyone thanks-but-no-thanks via a Fuse TV interview in which he answered a question about signing by casually saying, “I’m already a rapper, and I’m already kind of killing it.”  

Many factors aligned for Chance to become one of the most exciting and popular hip-hop artists in the country. Timing, opportunity, skill, a tight-knit team (his manager Pat Corcoran even goes by the handle Pat The Manager), and an unwavering self-determination came together like a perfect storm that has taken Chance from before to after in no time at all.

“That’s what it’s about. Everyday, doing something that will change everything,” he told me from the backseat of a passenger van last March. It was just two weeks after SXSW, roughly a month before the release of Acid Rap, and Chance was in the midst of a college tour with Kids These Days. It was a simple statement, but it speaks volumes about how he approaches his musical career, one taken very seriously and heavily thought-out. Chance’s rise to the top was almost entirely self-engineered, making his DIY methods an excellent example for any modern aspiring artist.

I recognized Chance’s spark when I met him for the first time before a hip-hop show at Chicago’s Sub-T in July 2011. For me, it was just another underground hip-hop showcase in which I was asked to DJ, but for Chance, it was his first gig at a true music venue, and his first time being paid to perform. I remember he was very excited. He had a sense of arrival. So many Chicago artists have come through Sub-T that the venue serves as a rite of passage to local musicians of all genres (I felt the same way my first time DJing on that stage). It didn’t matter that only twenty or so people had shown up when Chance started his early opening set - for Chance, all he seemed to care about was the fact that he was on stage and had introduced himself to Chicago’s hip-hop community. He was rocking the crowd as if it was packed, but what really made an impression on me were the low-key, vibed out first notes of “Brain Cells,” a song that would appear on his debut mixtape, 10Day. By the time his set ended with the now infamous “Fuck You Tahm Bout”, I was convinced. Recognizing my own role in Chicago to help break new artists, I tweeted, “@chancetherapper just killed his set at Sub-T. Never seen him before.” Boom, just like that - Chance the Rapper was in motion.

After that, Chance started sending me his music. On September 11, 2011, I posted his song “22 Offs” to Ruby Hornet (I was editor-in-chief from 2008-2013). It was his first ever blog post, and I started asking people, “you don’t know this dude, Chance The Rapper?!” As fall moved on, Chance talked to me more about his musical goals and aspirations. He made regular trips to SoundScape Studios, a historical recording studio in Chicago and home-base for my independent record label, Closed Sessions (I stepped down from my position at Ruby Hornet in February of 2013). He would play me his music, breaking down its intricacies and themes. I remember when he showed me the earliest version of 10Day, his debut mixtape that revolves around his 10-day suspension from Jones College Prep, a school in the South Loop known for its selective admissions process. 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. While some young artists try to stay aloof, Chance made it a point to be down-to-earth with his fans and the biggest promoter of his art. He regularly showed up at different Chicago area high schools passing out free CDs and hand-delivering tickets to his concerts. He wasn’t above posting up his own flyers or staying after his sets to interact with fans.

Shortly after I posted his music for the first time, Chance asked me to meet him at a Panera Bread just down the block from Jones College Prep, the high school that gave him the suspension that would change his life. I’ll never forget the meeting. As Chance broke down his plans for 10Day and beyond, it became clear that he was acutely aware of the fact that it was early September and while his peers were going off to college, he was living at home and sending his music to people like me, hoping someone would listen and open up some doors before his parents made him go to college or get a real job. I’ve had many similar meetings with other artists, but with Chance it was different because everything was so heartfelt and believable. He wasn't sketching pipe dreams or asking for handouts, he was speaking on strategy and attentively taking feedback, jotting things down in his notebook. He had no fear of hard work, and unlike many others, wasn’t interested in finding shortcuts. I knew from then that Chance could and would do anything. He would tell me a year-and-a-half later that he was also, in a low-key way, asking me to be his manager - something I didn’t realize at the time and still don’t think really happened. Regardless, Chance was on the come up and he knew it.

“Shit’s wild now. It’s crazy,” he told me just days after the release of 10Day, once again hanging out at SoundScape. “But I’ve been trying to prepare myself for this for so long, and convince myself that it wouldn’t even get to this point, but get to a point way beyond this… That shit is wild to me, but… I have so much further to go. I’m sure it’s strange for other people to see it happen, especially people who are just now coming on to what I’ve been trying to do and watching it unfold from a later date.” Chance told me that in April 2012, yet it feels like ages ago considering how much “wild shit” has happened since.    

Later that summer, just a year after our first meeting and about two months after the release of 10Day, Chance talked to me about his process. “Everything’s super mapped out and everyday I wake up and figure out a new goal, or a goal I haven’t reached yet, and kind of set into place how to get there.”

After the release of 10Day, Chance joined comedian/television star turned rapper Childish Gambino on a summer tour, securing an opening spot that gave him the opportunity to dissect how Gambino won over his audiences. Chance studied the crowds, figuring out which songs got them hyped, and made sure to include covers of Kanye West tunes to get them into unfamiliar music. He came away with a sharp understanding of the importance of sing-a-long records and set out to make his sophomore release more musically mature, yet still accessible. He struggled at first, feeling somewhat trapped by the success of 10Day and writer’s block. I asked him about it shortly after he returned to Chicago following the Childish Gambino tour. “I realized the music definitely comes from the artist,” he said about his writer’s block. “At this point I realized I don’t always have to write tapes about getting suspended from school.”    

Freeing himself from any self-imposed creative restrictions, Chance went to work on Acid Rap in summer 2012, enlisting the same crop of artists and producers that made 10Day an underground classic. The group included producer/keyboardist Peter Cottontale and jazz vocalist Lili K, who both pop up from time to time onstage as part of Chance’s live show. Other frequent collaborators include Vic Mensa, the former front man of Kids These Days who is one of Chance’s closest friends and influences since early high school, as well as other artists leading Chicago’s new class of musicians in their own right. The collaboration and creative process borrowed heavily from the acid jazz days in which talented musicians would gather together and jam. Chance made acid jazz’s aesthetic the foundation of his new mixtape, pairing it with a melodically experimental yet still technically sound flow that he picked up from his musical heroes like Souls of Mischief, Freestyle Fellowship, and perhaps the most prevalent, Kanye West. After all, it was Kanye’s debut College Dropout that landed in Chance’s hands during the 4th grade and changed his life forever. Since then, Chance wanted to be a rapper, and used Kanye’s musical fearlessness and sense of adventure as a guide consciously or subconsciously.

“The creative process for me is not something that's formatted at all,” he told me from the back of a tour van in late March 2013. “For me it's different every time and it takes me a long time to write music. It's always been something I go through, but it's always something I come out on top of.”

Chance’s belief in himself is not lost on those around him or those watching from the shadows of New York and Los Angeles. In fact, it’s a huge part of his appeal. Chance’s chief concern is making good records. Even on the most hectic of days, he seems to find peace in the studio. Once, during a jam session at SoundScape Studio with Montreal’s Purity Ring and Chicago R&B crooner Jeremih, he said “This is where I feel most at home.” Then he hit the road with Mac Miller.

“That whole ‘Mo Money, Mo Problems’ shit - it's kind of corny but I don't even have more money, and it's very serious,” Chance told me in the spring. “There are certain aspects of rap right now that don't necessarily have anything to do with hip-hop or music. It's a weird thing,” he paused. “Certain points in time I just sit by myself and think about what I want and what I want to do. I just sort of meditate on shit and you start doing advertisements, sponsorships and just random shit that has nothing to do with music. There's a business side to it, which I'm fully aware of, but it's not necessarily what I wanted.”

Chance may not want “the business,” but man, the business wants Chance. As he got closer to Acid Rap’s April release date, the talk of his potential signing got louder and louder until reaching a fever pitch when it was released. With 50k downloads in the first few hours, Acid Rap crashed two major hip-hop sites. “He’s got the whole world trying to give him a record deal,” said famed A&R/producer Dante Ross during a call-in to my Closed Sessions radio show. Ross is a music industry O.G. who has worked with artists such as Ol’ Dirty Bastard, Busta Rhymes, and De La Soul. He currently works for Warner Bros. and was one of the earliest non-Chicagoan industry professionals to get on the Chance bandwagon. “He’s going to be the new A$AP Rocky, he’s going to get one of those types of deals [rumored to have been worth $3 million]. And he’s done it with large amounts of patience, belief in his talent, and creating great music,” Ross added.

“I could've taken an offer in August of last year that was really good, but it was just not the right time I think,” Chance told me. By waiting and not immediately taking a major label deal, Chance is setting a new precedent, breaking the pattern of artists from Chicago signing big deals and then either sitting on the bench or squandering their opportunities.

It wouldn’t be right to explain Chance The Rapper’s rise to fame without talking about Chief Keef, another teenage rapper that the city of Chicago loves to hate, yet who has achieved major success for a teenager from Englewood. Dubbed the poster child for Chicago’s drill music scene, Keef was scapegoated into being the embodiment of everything wrong with Chicago - gang problems, youth violence, drug abuse (as well as bad weather, illiteracy, Derrick Rose’s knee injury, potholes, and parking restrictions). While Keef was inciting a bidding war for his artistry, he was also getting coverage in magazines, newspapers, and news programs for his out-of-the-office activities. Perhaps Keef’s most egregious offense came when he participated in an interview with the music site Pitchfork while holding a firearm at a gun range. That transgression landed him back in jail, right after the release of his major label debut, Finally Rich, which according to many in music industry did not perform as expected. It was almost a self-fulfilling prophecy.  

Keef and his crew supplied the country with what they expected from Chicago, both musically and socially, because they fed into stereotypes and reinforced negative images of poverty and violence-riddled communities. While some were appalled, others saw it as a joke or a scene from “Goodfellas”. Even t-shirts sporting the words “Chiraq” (a play on Chicago and Iraq) were produced and donned proudly by rich kids from the suburbs. Ironically, they sell retail online for $50, making it nearly impossible for kids actually from “Chiraq” to buy or benefit from these tees, further exploiting and patronizing their situation.    

No matter where you stand on Chief Keef or his music, it’s worth acknowledging that Keef’s rise from house arrest to a reported $3 milllion record deal shined light on many other Chicago artists who sign on the dotted line as soon as they get a chance. “Chicago’s got the most attention in the rap world that it’s ever had,” said Ross. Not surprisingly, he attributes that to Chicago’s drill scene. “It started with Chief Keef and all those guys,” he explained.

Keef’s influence is not lost on Chance, who gave him big ups in his statement song and video “Juice” when he melodically rapped, “city on the come-up, shout out my n***a Sosa,” one of Keef’s well-known nicknames. When I spoke to Chance back in March, just before the release of Acid Rap, he explained further. “I think the fact that Chief Keef came out and was repping his block and repping Chicago is one reasons why I'm able to do a lot of the shit that I'm able to do. He shed a lot of light on this city, and when you come out and you say the city's name it's something we can all be proud of.”

It’s an interesting choice of words from Chance, since he’s the exact type of artist and kid that has come to symbolize Chicago’s music scene opposite of Chief Keef. Although he does represent a more positive conception of Chicago and is a star for the city, his success doesn’t come at the expense of Sosa or any others. Chance makes it clear in his music and live performances that he is from the same struggle, also having lost friends to teen violence. Kevin Coval, a youth advocate and author of the book More Shit Chief Keef Don’t Like, has known Chance since he was a junior in high school. He says that while Keef and Chance differ in their expression, further distinctions should not be applied.  

“The reportage of the Chicago music scene is bifurcated in a similar way to the early 90’s scene in LA was,” said Coval, drawing parallels between what he sees as the journalist made separations between LA’s “gangster rap” symbolized by NWA and its “underground” symbolized by groups like The Pharcyde.

“The truth is that NWA and the Pharcyde and Keef and Chance come from similar neighborhoods and ultimately report on similar conditions albeit in different ways. And though I prefer Chance's music and lyricism, I think both are vital documents that speak for and with young people in Chicago in this moment,” Coval said.

If Keef is portrayed as everything wrong with the city’s treatment of its youth, Chance is everything that’s right. As referenced in “Juice”, Chance was raised on the south side in Chicago’s Chatham neighborhood and regularly talks about both of his parents throughout his music. Chance dedicated “Hey Ma” from 10Day to his mother, whereas Acid Rap’s “Everything’s Good” is about his relationship with his dad. Ultimately, both songs express a strong desire to make his parents proud. Perhaps the most telling line about Chance’s parents comes in one of Acid Rap’s stand out cuts, “Everybody’s Something” in which Chance raps, “I used to tell ho’s (change to “hoes”) I was dark light, or off-white, but I'd fight if a n***a said that I talked white, and both my parents was black, but they saw fit that I talk right."

The line explores a topic of identity and upbringing that many rappers never address, and for some, is non-existent. We would never hear such a line from Keef, or Durk or Chop, who didn’t experience the cross-culturalism that Chance was accustomed to during his childhood and adolescence at Jones College Prep, a prestigious private school that attracts and selects students from a range of socio-economic backgrounds throughout Chicago.

The music of artists like Chief Keef, Lil’ Durk, and Lil’ Reese paints a dark portrait of pain, poverty, neglect and nihilism. These guys made music with nothing but a computer and Fruity Loops while confined to a four-block radius, and in Keef’s case, while on house arrest. On the other hand, Chance The Rapper (“still Mr. YOUMedia”) traveled regularly to Chicago’s cultural and creative hubs to cut his chops and earn his stripes in neighborhoods like Hyde Park, Wicker Park, the South Loop, and Ukranian Village, with mentors and guides helping him along the way. If Keef’s music comes from isolation and segregation, Chance’s comes from exposure and experience. They are two sides of the same coin, and Chance’s emergence allows Chicago’s hip-hop and its youth to be viewed from a broader spectrum. That said, we can’t lose sight of the fact that Chance was still exposed to all the city’s ills as well, which gives him the type of kinship with Keef and others that he expresses on 10Day’s “Missing You” and Acid Rap’s “Paranoia”.

Dante Ross said it best, “Chance The Rapper is the yang to the ying with the drill scene. He’s kind of the opposite,” he said. “I think since Chief Keef got all the attention and the success he had, the spotlight has been on Chicago a lot more. And made it a lot easier for Chance to get all the focus he’s gotten. On top of that, Chance is an amazing artist, and he’s actually bigger than rap in a way. He’s someone who probably has a chance at lasting impact.”

The truest test for Chance will be staying power. You can’t be the newest hip-hop darling forever, just ask Trinidad James, Kreayshawn, A$AP Rocky, Papoose, or countless others. But Chance is making all the right moves, and showing that he is not in it for a quick buck. He may seem like an overnight sensation to those who’d never heard of him before Acid Rap, but in reality he is the product of years of hard work. He is still that same kid who loses himself in the studio, and treats people with kindness and humility. “I've never thought better of myself because I've succeeded in spreading my music, or because I'm on tour or whatever people look at it and see as something to brag about,” he told me. “The only thing I brag about are my hot rap skills, cause I'm fire on the mic. But, that's not really enough to brag about. The best way to do that is to just make hot songs.”