of youth in Chicago through arts education, mental health
services, warm-clothing drives, and more. Bennett has donated $2 million of his own money to SocialWorks’ efforts—
including $1 million to Chicago Public Schools and $1 million to Chicago mental health initiatives.
In late August, Corley gave birth to the couple’s second
daughter, Marli. It was this development that caused
Bennett’s already packed schedule to melt down—he felt
he couldn’t be a new father and go on tour at the same
time. Eleven days after Marli was born, he announced,
via Instagram (and a photo of himself with his girls), that
he’d be postponing his heavily anticipated, 31-stop North
American tour until January.
Yet he kept his promise to Chicago. On September 28,
he performed a single show for a crowd of tens of thousands, which featured his brother, Taylor, and Chicago
native Kanye West. The decibel level in the United Center,
home of the Chicago Bulls, reached levels that rivaled the
Michael Jordan era. Chicago was simply another loved
one whom Bennett couldn’t disappoint. As he says himself on his 2018 track “I Might Need Security”: “I’m a sign
to my city like the Bat-Signal.”
Chicago is a city segregated by a river, which slices it
horizontally. Head north, past the old money of Lincoln
Park (where the public schools are highly rated); past the
Cubs fans at Wrigley Field (which charges some of the
highest ticket prices of any MLB stadium); past Edison
Park (statistically one of the safest parts of the city, where
a disproportionate number of law enforcement officers
hole up at night); past the liberal enclave of Evanston
(home of Northwestern University); and you’ll reach affluent, 90% white suburbs.
Head south, past the Loop business district, and you’ll
start to understand the place from which Bennett draws
his inspiration, both musically and civically: the selective-enrollment Jones College Prep (where Bennett went to high school);
Harold Washington Library (where he recorded parts of his first mixtape); the White Sox’s Guaranteed Rate Field (which charges among
the lowest ticket prices in the MLB, and where Bennett launched Social Works while promoting his third mixtape, Coloring Book, in 2016).
Keep going, and you’ll reach Hyde Park (the predominantly black
intellectual stomping grounds of the Obamas and also, incidentally,
where Bennett, at age 9, first heard a track by Kanye West on the radio, which inspired him to buy College Dropout, the first rap album he
ever listened to) and eventually the heart of the South Side, an area
most Americans know only as a gun violence caricature.
Abutting this part of Chicago is a middle-class neighborhood
called Chatham, where Bennett was born. He is among the fourth
generation of Bennetts to have lived on the same block, and his
music, friends, family, and Christian faith remain rooted here. It’s
for this reason that he runs his business differently from perhaps
any major entertainer working today. Bennett has no Hollywood
agent or manager on retainer. There’s no slick branding agency or
says Chancelor Bennett, aka Chance
the Rapper. It’s 9 p.m. on a fall evening at a
Chicago recording studio, and he and his
bandmates are packing up for the night.
Four days from now, they will put on their biggest show
of the year, at the city’s United Center.
Bennett sits next to me in high-waisted track pants
and a fitted tee. He admits to feeling a little overwhelmed
by having a new baby at home and a new tour to prepare
for, and yesterday was proof. He had taken his 4-year-old
daughter, Kensli, to Dunkin’ for a rare treat before school.
It was the first day all week that he had been able to do
morning drop-off, and he’d wanted it to feel special.
She picked out a glistening, sprinkle-topped chocolate
doughnut, and he realized his pocket was empty.
“It’s just a crazy letdown for a child,” he says, shaking
his head, clearly still unable to forgive himself. Luckily,
another customer was more than happy to pick up the
tab—in exchange for a photo with Chance the Rapper.
The entire span of 2019, in fact, has been rather frenzied
for the 26-year-old, who made the unthinkable choice several years ago to eschew record deals and give his music
away for free. He’s garnered more than 1. 5 billion streams
on SoundCloud since 2012, and he’s earned millions of dollars in revenue, through live shows, merchandise, and endorsements instead. Last winter, he filmed six episodes of
Rhythm and Flow, a Netflix talent competition that he hosts
alongside Cardi B, T.I., and a slew of R&B royalty, which debuted in October. In March, he celebrated his wedding to
longtime girlfriend Kirsten Corley, a childhood behavioral
therapist and Kensli’s mother. In July, he released The Big
Day, his first official full “album” (previously, he had released three “mixtapes”—the last of which snatched three
Grammys), which became a Billboard No. 2 hit. He made
his feature-film debut in July with a cameo in Disney’s The
Lion King remake. In October, he hosted Saturday Night Live
for the second time, also serving as musical guest. During
all of this, he was also helping to run Social Works, the nonprofit he founded in 2016 that works to improve the lives
I LEFT MY WALLET