WHAT CHANCE THE RAPPER’S ‘COLORING BOOK’ MEANS FOR CHICAGO AND THE FUTURE OF MUSIC

By Jake Krez (Originally Appeared for Pigeons & Planes)

It’s nearing ten o’clock on May 12 and I’m sitting in a line of bumper cars to the right of Chancelor Bennett as he tugs down on his cell phone screen again and again.

On the other side of Chance his little brother, Taylor, buckles himself into his own car. In a few minutes, Chancelor, better known to the world as Chance The Rapperwill unveil his long-awaited follow up to 2013’s Acid Rap. As he continues to refresh the Apple Music page from the comfort of his plastic seat Taylor leans over to peek at his phone, asking the question on everyone’s mind. “How does it feel bro? Do you feel older?”

He gets his answer only moments later as Chance, leaning back in his seat and holding his phone to the sky, lets out a euphoric shout, “I’m relieved!” Coloring Books is now available for streaming. While some may have celebrated with lavish parties, champagne-soaked soirées or a star-studded performance, Chance instead tucks his phone back in his pocket, nods to the Whirlyball operator in the box overhead and proceeds to chase his friends around an aluminum court in bumper cars, followed up by free pizza and french fries.


Such is the norm for an artist who has grown into one of the most recognizable figures in rap and music at large through his ingenuity. Despite not having released a true solo full-length project in three years, Chance has asserted himself in pop culture by eschewing many of the tropes that come associated with such success. While he’s certainly found friends in high places—Coloring Book features Kanye West, Lil Wayne, and Ty Dolla $ign, among many others—he’s also been careful not to forget who he is and where he came from. Chance is staying proudly independent.

It’s a sentiment that’s reflected in his music and has in turn laid the foundation for a sort of artistic renaissance in his hometown of Chicago. It’s a sentiment that is at the center of this most recent offering and one that is undeniable in its importance. The story Chance tells throughout the trilogy of his first three mixtapes is the South Side’s story, the scene’s story, my story, our story; the story of a city on the make.

These days in Chicago, it’s hard not to walk past a bus stop, drive down the highway, or log onto the Internet without seeing Chance’s face. Since the Brandon Breaux-designed artwork dropped earlier this month it’s been literally plastered everywhere; a communal nod of acceptance for a city long known for its divisiveness.

Chance has not simply delivered a trifecta of projects, he’s done so by channeling some of the area’s greatest names in the process. His brash sensibilities and eagerness to speak his mind is pure Kanye. His careful, nuanced approach to live performances, which have featured plenty of fancy footwork and mic stand drops since day one, is inspired by Michael Jackson. Coloring Book has come out in his Jordan year—Chance turned 23 in April. Chance The Rapper is Chicago.

The new project is the end of a long road for the Jones College Prep graduate. Whereas most acts today take advantage of the Internet and social media by releasing music at a fever pitch, Chance’s full-lengths have manifested themselves as a calculated response to his own life. 10 Day opened the door, Acid Rap served as the walk through the entrance, and Coloring Book is his grand statement once inside. The delivery is precise, the messages clearer and more pronounced. If there were any questions as to what Chance is aiming for with his career, it becomes obvious on this project that he’s focused on the top without forgetting the bottom.

Chance is focused on the top without forgetting the bottom.


As the clock hits 11:30 p.m. those still at Whirlyball leave and head to the release party at Soho House. Exiting the elevators on the fifth floor with Social Experiment producer Peter CottonTale, we’re greeted by a huge sea of people, certainly more than is typical for near-midnight on a Thursday, all buzzing with the excitement of hearing the new album.

A week earlier the room was considerably less crowded as I sat at the bar with Chance’s dad Ken Bennett talking about the impending release. “Jake, this album is Chicago,” said Bennett, grabbing my elbow and looking into my eyes. “Seriously, though, this is the one, no one’s going to be able to deny it.” The album is out in the world now, and it’s hard to argue with the thoughts of the man who worked alongside President Obama. All else aside, Coloring Book really is an album that speaks to the sensibilities and ideology of those that live and work here in Chicago, in the Midwest.

chance-coloring-book-essay

Image via Yakub Films


Earlier this year Chance The Rapper was named one of five Chicagoans of the Year by Chicago Magazine. It’s a title he earned through both his success in music and his initiatives to help his city. There are the obvious: his Open Mike seriesoffering high school kids an opportunity to perform in front of one another, theWhite Sox collaboration, the endless positivity in his music. What’s a bit less obvious is the true effect all of these things have on the place he was raised.

For generations, Chicago has been a place where music formed. From Chicago style Jazz and Benny Goodman to Blues and the birth of rock music, all the way through to House and Frankie Knuckles, the city has never been at a loss for good music that pushes the envelope. What it doesn’t have is a true industry, a fact that has sent many talented artists scurrying for the coasts, desperate for a break. Not Chance though.

In the wake of Acid Rap there were plenty of offers being thrown around, and from the sounds of songs like “No Problem” that may still be the case. It was around that time that Chance was in the basement of a house I shared with CottonTale, discussing whether or not to rent a place in Los Angeles, whether to move and make the transition so many had before him. While the Social Experiment team did relocate for a time, Chance has made a concerted effort to keep his music in Chicago, working with Chicago artists, and it shows.

Whereas Chance’s choice to release his music free and independently might seem like small potatoes to anyone paying only casual attention, it’s a serious conversation that could help change the way we consume music. Here in Chicago, we make use of what’s around us to succeed. Not seeing any labels nearby or willing to play the game he wanted, Chance instead formed Chance The Rapper LLC, produced his own merch with a contingent of dedicated creatives, and built his own successful business.

Because of Chance, there is a thriving community that has taken ownership of their work and their art and found success in the process.

It’s a move that’s important for its musical consequences, but it has also opened the eyes of artists and entrepreneurs across the city. Because of Chance, there is a thriving community that has taken ownership of their work and their art and found success in the process. One such example is Austin Vesely, longtime director of Chance’s visuals who announced his debut full-length movie, starring none other than Chance himself. It’s of course an independent movie. Vesely is not the only example. Chance has placed NoName Gypsy, Saba, and a slew of local artists on all of his projects to date, thus bridging the gap between his hometown friends and those at the top of the industry.

Last week a petition for free music to be eligible for Grammy nomination began circulating. Coming just ahead of the release of Coloring Book, the petition has racked up over 30,000 signatures. About a year ago, I was sitting across a counter from Chance in his old apartment the day after SURF was released. As he paced back and forth across the bright room with glass walls, he spoke about winning the first truly independent Grammy, what it would mean to the city and the industry at large.

SURF made waves by being the first official free release on iTunes, as Chance pushed boundaries of what “independent” can mean. It was his first attempt at earning a gold statue without adding a price tag to his work, but a Grammy win for Coloring Book would be a true affirmation of everything he’s been pushing towards and a coronation of Chicago as the next great hub for new music.

Image via Yakub Films

Image via Yakub Films


Coloring Book is the perfect ending to a trilogy, the coming of age of Chancelor Bennett as he grows from high school teenager to father. He makes music that’s able to reach deep inside a listener. If art is meant to reflect life, his ability to take small personal moments—getting suspended from school, feeling lost in the world, talking to his grandma on Sunday—and create all-encompassing pieces of work that truly evoke the thoughts and feelings of those memories is unmatched.

“Juke Jams” operates as an ode to late nights in dark basements exploring the opposite sex, a true Chicago tradition that finds a national audience with Justin Bieber on the hook. “Blessings” with Jamila Woods feels like Chance speaking to his daughter, a constant theme of the project that even appears in the cover art, which depicts Chance looking down lovingly at her.

“How Great” with Jay Electronica boldly underlines the driving ideology behind his work so far. Hearing Chance rap, “I believe in signs/Don’t believe in signing, I seen dollar signs/Color white collar crime,” it’s impossible to not feel the intensity and urgency of the message. That it all comes packaged in a coat of gospel simply plays to the place in life Chance finds himself today. It’s music that Chicagoans for the most part feel palpably connected to. It’s something that was obvious with the name dropping on 10 Day, evident throughout references on Acid Rap, and fully intertwined in his latest release. Coloring Book acts as his opportunity to show off the hometown he’s created and experienced for himself, in that regard his father was absolutely correct.


Standing amongst a crowd of creatives, well-wishers, and a cross-section of the city’s best and brightest, Chance shines the most without sticking out. Wearing a simple long sleeve blue shirt and now-iconic 3 cap, he appears distinctly understated. Despite being just hours removed from releasing the biggest project of his career, Chance moves about the room like the humble backpack rapper we first met at a listening party at Leaders 1354. Doling out handshakes, high-fives and hugs and dancing deep into the night, Chance seems right at home amongst old friends and new fans. A little after two in the morning he quietly slips down the elevator arm in arm with the mother of his newborn child.

Chance has come a long way in the five years since 10 Day and he’s brought his city along with him. The range of possibilities in his hometown are growing wider as a generation learns to take things into their own hands. It’s a movement we’ve come to call the Chicago Renaissance and one that has and will continue to be very much led by Lil Chano from 79th.

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