Chicago's Chance

Chicago's Chance

How Chance the Rapper’s Prideful Ambition Is Reshaping Chicago’s Cultural Narrative

Written by Alec Stern


“Whoever said the sky was the limit, wasn’t living where I was living”

-TheMIND, “Mercury Rising”


At the end of his star-making verse on “Ultralight Beam”, Chance the Rapper makes a grand declaration. “You cannot mess with the light. Look at lil’ Chano from 79th.” On first listen, it is an announcement of his newfound stature as a superstar, and especially when debuted on the Saturday Night Live stage, it was easy to believe his light would be both undeterred and seen far and wide. But this final couplet can also be read as a plea. “Look”, he says. “Look”. He’s asking for you, the listener, to be active. It is a line that boasts not only where he is now, but also where he was then. He wants us to know where he came from, but even more, he wants us to really see this place. Because he knows what we will find there when we do.


The creation of art has always been used as an expression of experience, as well as a device in the search for a greater truth. In the last few years, we’ve seen an unprecedented and inspirational influx of artists innovating with new soundscapes, questioning the status quo of distribution, redefining the relationship between artists and fans (and vice-versa), and injecting profoundly essential perspectives on matters such as race, sexuality, individuality, and the realities of those often without a voice of their own. In past and present, the artists who trailblaze and transcend are the ones who provide an essential sense of humanity to the people and places they know firsthand; places begging to be heard on their own terms. These are all-too-often disenfranchised communities, laden and crushed beneath stereotypical narratives they neither own nor believe in. The South Side of Chicago is like this; it is a place most feel they know without stepping foot inside it. With each passing day, and with each news cycle, the city’s story becomes harder and harder to be written or read as anything other than self-fulfilled and beyond hope. But what if a place was able to speak for itself and tell its own truth? In the last year, Chance The Rapper has manifested as a surrogate for the city of Chicago, and by offering an honest and unique take on his surroundings, remaining independent of major labels, and by injecting a profound sense of hope, positivity, and pride in his hometown, he has provided an opportunity for Chicago to shape its own cultural destiny, and has managed to bestow the brightest of colors within a city literally and figuratively seen as black-and-white.

On August 11, 2016, Chance the Rapper graced the “New Pioneers” issue of Billboard Magazine, celebrated the three-month anniversary of his monumental mixtape Coloring Book, starred in an Olympic advertisement for Nike in which he premiered a new song “We The People”, and was featured on the President of the United States’ official Summer Playlist. On that very same day, The Chicago Tribune reported that nearly one hundred people had been shot within the city that week alone. Three days prior had been the deadliest day in Chicago in thirteen years, with nine people murdered over the twenty-four-hour span. One of the victims was a ten-year-old boy: he was shot in the back as he played on his front porch. It is difficult to comprehend how these two realities could possibly exist at the same time, or how a place can simultaneously swallow so many lives while also catapulting a single young soul to uncharted new heights. But in a way, that has always been the tale of Chicago, as it is one city with two extremely distorted and segregated realities; two faces, two identities, two truths.

When “Chi-Raq” became a common phrase in rap songs, on t-shirts, and even as the name of a Spike Lee-directed feature film, it was referring to the South Side of Chicago and the city’s severe murder rate. Chancellor Bennett was born in West Chatham, about ten miles south of Downtown Chicago, and while it’s not the most impoverished neighborhood on the South Side, his surroundings often resembled the war zone that inspired the city’s most recent nickname. We know this because it’s in the music. As listeners, there is so much we know about Chance, and that is because he has always been unapologetically transparent about his life, his home, and most importantly and uniquely within hip hop, his feelings: particularly in regards to violence. For decades, rappers from N.W.A to Kendrick Lamar have incorporated and repurposed violence and street aggression in their music as an artistic lens to illustrate their own reality. The South Side itself has often been a focal point of violent music, most recently with the rise of Drill, a style of hip hop routinely labeled as the ‘theme music to murder” for its sensationalistic influence on children and teenagers, as well as its transparent motivation in capitalizing on society’s prevalent voyeurism for violent culture. On the other hand, Chance the Rapper has taken a conscious approach in his written perspectives on violence, a style similar to that of Common, Talib Kweli, Mos Def and Nas, and has injected a wholly unique and revelatory stance that is as childlike in its innocence and optimism as it is mature in its thoughtfulness and accountability. These viewpoints are on full display throughout his discography, and are particularly incisive on the song “Paranoid”:

“Cause everybody dies in the summer

wanna say ya goodbyes, tell them while it’s spring.

I heard everybody’s dying in the summer

So pray to God for a little more Spring.”

These are not prideful boasts, scare tactics for power and popularity, or shock value for the sake of entertainment. This is more tangible than that: this is vulnerability. It is one thing for an artist to take a stand against violence, which Chance has made a key platform within his influence, but it is another thing altogether for someone to expose such a profound and universal fear of its grip on one’s friends, family, and hometown. Many have deliberated hip hop’s uniquely intrinsic relationship to violence as both a product of and reaction to the fundamental role violence has played in the black American experience. Through this lens, Chance’s music can be understood as both a tool for personal self-expression and as a conduit for a larger-scale dialog and understanding. And while an artist’s relationship to their audience can often be similar to that of a therapist and patient, Chance has never asked his fans to pay to hear his feelings.

From day one, Chance’s homegrown, do-it-yourself philosophies have been the cornerstone for his career growth, and his tremendous development has mainly been achieved through a persistent and uniquely executed emphasis on person-to-person connection. This distinct focus has allowed for Chance to build a grassroots community of followers from West Chatham to the rest of the globe in an impressively organic fashion. There is a tangible brilliance in Chance’s understanding of the ways a sharing community can elevate not just a man, but his message. This has invited a certain degree of folklore to everything Chance is and does, particularly in the ways he has established himself outside of the traditional ideas of what an artist is and does. In some ways, Chance The Rapper has become more of a symbol than the twenty-three-year-old he really is, and this is largely due to what is arguably his most unique asset within the music industry: his resolute stance and ability to remain independent of major labels. As an independent musician, Chance has no contractual obligations to a record label or publishing company, which allows him complete ownership over his intellectual property and his brand. These are fairly new concepts within mainstream music, and while it is an inherently risky strategy to work outside of the system, independence has played an enormous role in his success. Perhaps his most pioneer move of autonomy has been his resolve to give his music away for free, as both a nod to mixtape culture and as a forward-thinking experiment on what a 21st century career in music could look like. He has turned the once-revolutionary idea of free music into a serious consideration for artists and industry heavyweights alike. For example, with the album Surf, the band The Social Experiment’s debut on which Chance was heavily featured, he convinced Apple to release it on the iTunes Store for free. It was the first and only time the tech giant had done so with a full-length album, and as a result, Surf was downloaded 618,000 times in its first week, with over 10 million individual track downloads. It is also likely not a coincidence that shortly after the release of Coloring Book, the Grammy’s overturned a previously unyielding guideline that prohibited albums not sold through traditional retail methods to be considered for awards. Simply put, the world wasn’t ready for a trajectory like Chance’s until very recently, which is one of the reasons why he feels like one of the most now icons we have. In an industry of artists and corporations chasing taillights, the masses have found something incredibly admirable, thought-provoking, and hopeful about Chance; he is the outsider leading the pack to something new and brighter.

Choosing to exist as an independent artist has established Chance the Rapper as a leader within both the music industry and his own community largely due to the freedom it has allowed him in telling Chicago’s story in a truthful, unique, and authentic way. It has allowed him to speak on the ugliness and beauty of his home with no censorship or political ties. It has allowed him to build an organic career with a home-grown base of devoted fans that have propelled him out into the world. It has allowed him to experiment, to be constantly interactive with his followers in new and exciting ways, and to release all of his music for free. It has allowed him to stay in the city he loves- a city where “every father, mayor, and rapper jump ship”- and to embark on a mission to make the South Side better for his daughter than it was for him as a child. Chance is a symbol for Chicago; a “blueprint to a real man” as he calls it. By remaining independent, he has made something of and for himself against all odds. Through his example, there is reason to believe in Chicago’s ability to do the same.

In September 2016, Chicago Magazine posted a list of young Chicagoans who are bringing a positive change to Chicago through the arts, and all of them were in some way connected to Chance. There was Jamila Woods, who put out her own groundbreaking album this year, Heavn, as a celebration of “black girl magic” and sang the chorus on the Surf hit “Sunday Candy”. The Social Experiment, led by Nico Segal (fka Donnie Trumpet), acted as Chance’s backup band during his Muhammad Ali tribute at the ESPYs. Austin Vesley, a rising filmmaker on Hollywood’s radar, shot the “Sunday Candy” video, and is wrapping his feature film debut “Slice” staring Chance himself. Outside of this list are other revolutionaries within Chance’s orbit, such as Vic Mensa, who made headlines with his protest anthem “16 Shots” for Laquan McDonald, Noname, who has been featured on nearly every “Artists You Need to Know” list of 2016, the relentless visionary poet/activist Malcolm London, and the trailblazing visual artist and storyteller Hebru Brantley. Every one of these artists have made their Chicago upbringings a staple in their work and social messaging, and have combatted the very idea of negativity with unique talent and a collaborative spirit. It is as if all of these mavericks are working together toward a common goal: to reimagine the Chicago story from the inside out and to finally displace the fear within and of their city with excitement, happiness, hope, and love. People are beginning to take a much-needed second glance toward Chicago, and it is because of these “New Bohemians”, as Chicago Mag labeled them, and the stories they are telling. However, while this artistically-energized scene has caused a fascinating, groundbreaking, and vitally potent shift in the way Chicago is viewed from both the outside-in and the inside-out, the critical foundational changes needed within Chicago will likely take years, decades, or even lifetimes to take shape. No one expects a song to repair the division and brokenness this city has experienced, nor for it to fully convert the perceptions of the larger public. But there is hope to be found in the youth of this city. Through politics, social movements, and even music, the next generation often carries the burden of belief that they will be the ones to really change things. There is undeniably something happening in Chicago right now, and it is being assisted and soundtracked by a vibrant, young, communal, and artistic proclamation of faith, redemption, and hope. And for the South Side, this embrace of light is nothing short of radical.


Coloring Book, to steal from Chicago’s own Kanye West, is a pure “Ultralight Beam. It is so unrelentingly positive and overflowing with joy that it feels both revelatory and somewhat out-of-time within the grimness of 2016. It is a portrait of a man who has risen above negativity in all its forms, stood tall against convention, brought beauty out of ugliness, and most inspiringly, continues to reach back to help others climb their own heights. Outside of music, Chance has dedicated his time, talents, money, and influence toward making a real difference for those in Chicago who need it most. For instance, Chance has continued to host open mic events for high school students seeking an audience and an opportunity to perfect their skills. He has personally chaperoned groups of young children to several Chicago institutions that are often out-of-reach for residents of the South Side. He began the social media trend #SaveChicago to attempt to stall murders for forty-two hours over Memorial Day, a historically violent weekend in his hometown. He established the Warmest Winter program, which provides homeless men and women in Chicago jobs creating convertible coats and sleeping bags for fellow homeless people in the city. Most recently, he led a march of thousands of impassioned young voters through the bustling streets of Chicago to a voting station the night before the election. But perhaps above all, he has made music that gives people a genuine sense of happiness when they need it most, tending to release his mixtapes as summer approaches and murders are on the rise.  He’s created a world in his own image, and has inspired a generation in doing so. This was arguably never more apparent than on his Magnificent Coloring Day, which took place at Chicago’s Guaranteed Rate Field this September. Featuring Alicia Keys, John Legend, Skrillex, Lil’ Wayne, and others, it was the first concert held in the stadium in over ten years, and it blew away the previously held attendance record for the venue. It was a day specifically designed to celebrate the spirit of Chicago, and to show the true beauty the city, particularly the South Side, and its people have to offer. Fans flew from around the world to witness Chance’s bold homecoming and were treated to a truly joyful embrace of music, culture, and rousing self-love. Kanye himself even showed up for a set, proclaiming enormous pride in the major accomplishment Chance had put together, the likes of which he himself had never managed. If Kanye’s appearance proved anything, it was that while he will quite possibly always be Chicago’s most notorious musical son, a torch has been passed to the next generation of artistic and social genius within this city. It was here, seeing Chance’s arm slung over Kanye’s shoulder as they walked backstage laughing, that it was most clear: this is a city of family, of art, of hope, of revolution, of imagination, of humanity, and of possibility. Just as Chance has emerged as Kanye’s heir, it is almost guaranteed that his own fame and accomplishments will open the gates for the next generation of young and passionate visionaries to further his message, and to continue to paint a three-dimensional picture of the city. Above all, this will surely be his greatest gift to the place he calls home.


It is now Chicago’s turn to take the opportunity Chance has provided, and run with it. Chance the Rapper has turned a spotlight on this city and is doing everything in his power to reflect brilliance and hope back to the world. Chicago Magazine recently named him “Chicagoan of the Year”, and there are already murals of Chance painted near his childhood home in West Chatham, which has become something of a tourist attraction. It is unknown if any political movement will result from Chance’s efforts, or what the widespread cognitive shift that he is continuing to inspire will lead to. But regardless of what the city does next, Chance has humanized Chicago and the people it has forgotten, and in doing so, has created fundamental change. Whether it is wearing a White Sox cap in his national TV debut, or proclaiming “City so damn great I feel like Alexand” in his hit “Angels”, his message serves as a constant and prideful reminder of where he is from and what we can all aspire to be. Chicago has always been a deeply and painfully segregated city, and particularly on the South Side, it can often feel like its own world; one that most people will only be exposed to through images on a screen or through the words in a song. There is enormous power in being the gatekeeper of a larger public opinion, and through his stance on violence, his leading example of independence, and by remaining forever true to his home, Chance the Rapper is inspiring a magnificent and divergent South Side movement to show not only what Chicago is and was, but what it can be.


The cover of #10Day, Chance’s first mixtape, sees him as a kid. He’s looking up at the sky, his mouth agape with awe and wonder at the hugeness of the world beyond him. You can almost hear him asking “What’s out there for me?” On Coloring Book, Chance the Rapper looks down grinning as if to say “Big fella, you’ll see soon enough.”

Alec SternComment