“Having that amount of time without a strict dad, just, like,
hanging out—and everybody is starting to buy guns, get
into drugs, have sex, grow, and make their decisions. . . .
I was running it up.”
Cunningham and Smith went off to college. Bennett,
who wouldn’t graduate from high school with the rest of
his class, didn’t. “It was a weird space for me,” Bennett
says, recalling how it felt to have his friends move on
while he stagnated, dreaming of a career in rap that felt
far from attainable. “So when I didn’t go to school or get
a job, obviously, [my dad] kicked me out,” says Bennett,
who spent the next year couch surfing at friends’ places.
A fe w days before Bennett’s United Center concert, Ken
Bennett sits in a nearly empty stadium on the suburban
DeKalb campus of Northern Illinois University. Bennett
and his band have set up a stage mimicking the United
Center’s, complete with 30-foot screens and strobe lights,
and the bass floods my body as they perform and tweak
songs until they get them right. Ken sits with his head
tilted back, eyes closed in a relaxed micro nap. He’ll rouse
himself later, bobbing his head to the music, as Bennett
and Taylor perform “Roo” onstage. The lyrics credit Ken for
instilling a bond between the brothers but also address the
hole that opened when he left for that year.
Bennett may have been a terrible student, but he
still learned a lot during his high school years. Through
Chicago Public Library’s YouMedia studio, a creative media lab at Harold Washington Library, he honed his rap
skills and recorded an album. A mentor named “Brother
Mike” Hawkins ran a weekly open mic night for Chicago
schoolkids. The rules were simple: Three minutes onstage,
and no racism or sexism. Hundreds of teens would show
up, so not everyone could perform. Somehow, though, Bennett’s name would consistently float to the top of the list.
“I remember, I had the song ‘Brain Cells’ . . . and I would
perform [it] every week. And at one point, Brother Mike
came to me and was like, ‘Yo, if you perform that song
again next week, I’m not going to let you perform [any-
more],’ ” Bennett recalls, lying on the concrete arena floor
and using his denim jacket as a pillow. As the setting sun
shines through the building’s lone set of windows behind
us, he cheerfully admits he’s half asleep. “A lot of people
have different theories about how I came up . . . but truth-
fully, the lessons that I learned and the fans that I gained
all came from when I was doing open mic.”
During that uneasy year after high school, Bennett says,
he was out one night in tony Lincoln Park with his older
friend and aspiring rapper Rodney Kyles, when a “big-ass
fight” broke out. Kyles was stabbed by an unidentified
man who would never be caught. That evening, from the
hospital where his friend died, Bennett phoned his father.
“It was the first time I had called him in a long time.
He picked me up, and I came back home, and I just stayed
there. And then I lived there,” says Bennett. Not long after that, Ken quoted a line from
Even after he postponed his scheduled tour,
it’s been a heck of a busy year.
The Big Day, Bennett’s first full-length album,
debuted at No. 2 on the Billboard 200 in July,
making it his highest-charting release.
In addition to a September show in Chicago, Bennett headlined London’s Lovebox Festival, the Life is
Beautiful festival, and the iHeartRadio Music Festival.
Bennett’s vocals appeared on tracks by YBN Cor-dae, Supa Bwe, 2 Chainz, and Guapdad 4000.
Bennett produced and cowrote a song for
September’s film version of Rebecca Sugar’s progressive animated series Steven Universe.
THE LION KING
Bennett surprised audiences with an unannounced cameo in Disney’s July remake.
RHYTHM AND FLOW
The Netflix talent competition show, which
debuted in October, features Bennett as one of
its celebrity judges.
BETWEEN TWO FERNS
Bennett made a cameo in the film, which came
out in September.
Bennett starred with the Backstreet Boys in an ad
that aired during the 2019 Super Bowl.
Bennett oversees and often hosts this event,
which invites Chicago high school students
to perform music, poetry, and dance onstage.
This four-year-old effort collects donated winter
clothing and distributes it to the homeless and
transient population of Chicago.
Social Works builds arts and literature programs
in dozens of Chicago public schools. (Bennett has
donated $1 million to the school system.)
KIDS OF THE KINGDOM
This Christian summer day camp was
founded in 1978 by Bennett’s great-grandmother.
(His 4-year-old daughter is a camper.)
MY STATE OF MIND
Bennett has personally given $1 million to the
mental wellness fund, which pledged $600,000
to local service providers in 2018.
Bennett bought the 15-year-old local
news site in 2018 and is rebuilding it as an
app that connects users to art, culture,
and food in the city. (Continued on page 100)