Chicago rapper Taylor Bennett wants everywhere to be a place black people can be themselves

Navy Pier has been a refuge for rapper Taylor Bennett and his homies for years. They aren’t drawn to it for the obvious reason, though—that is, free admission to 3,300 feet of restaurants, shops, theaters, and parks, with regular firework shows, spectacular views of Lake Michigan, and a Ferris wheel that’s just as iconic a part of Chicago’s skyline as the Sears Tower. (We refuse to call it the Willis Tower.)

Rather Bennett started coming to Navy Pier because it’s one of the few places in downtown Chicago where black kids from the south and west sides can meet in peace. On the Magnificent Mile, by contrast, it’s easy for black teens to feel othered, surrounded by a sea of white shoppers who respond to the sight of them by clutching their expensive bags tighter. Those blocks are also a hot spot for profiling and harassment by cops—on horses, on bikes, and in cars—who’ll break up groups of black kids and order them to leave, sometimes while hurling racist invective.

Bennett is 22 years old now, but he clearly remembers being accosted as a teenager by a CPD mounted patrol officer. He was hanging out at Chicago and State, an intersection popular with teens for its proximity to McDonald’s, Water Tower Place, and the beach. “‘What are you doing here?'” he recalls the officer saying. “‘Go back to your neighborhood.'”

It still happens today too. This March, six black teenage boys were kicked out of Water Tower Place for “loitering” and not being “engaged in the shopping experience,” according to the Sun-Times. Obviously such policing is willfully blind to the reasons teenagers come to places like this: Who didn’t used to go to the mall on weekends, by train or by bus or by somebody else’s car, to hang out with friends and flirt with crushes? Ford City, Evergreen Plaza, North Riverside, and the Brickyard were all go-to spots when Bennett was that age, but Water Tower Place had an aspirational glow that almost every black teenager wanted from time to time.

Of course, that’s not to say Water Tower Place welcomed Bennett and his friends. “Because we’re black, we didn’t fit the demographic of the standards that they felt their customers wanted to feel when they walked into a store,” he explains. “We were banned from those places. We were pushed out of those places.”

That’s part of what led Bennett to Navy Pier. For many young black Chicagoans, it’s filled with childhood memories: trying to buy a cheap souvenir with leftover lunch money, watching Michael Jordan to the Max in the IMAX theater, racing underneath the arcs of water shooting between the fountains in the Crystal Gardens till a chaperone yanked you back. Some of us, Bennett included, would have eighth-grade luncheons on one of the cruise boats.

Bennett grew up in the south side’s West Chatham neighborhood alongside his older brother, Chance the Rapper. He remembers taking annual field trips to Navy Pier. On one visit with his childhood day camp, he hung on to the outside of an escalator—something he and Chance used to do for fun—and accidentally ended up riding it to the second floor.

“I held on to it and I got too high, afraid to let go, and I had to go all the way up to the top,” Bennett says. “Literally everybody in the whole Navy Pier was looking at me go up this thing, and this guy just grabbed me when I got to the top. I got a whupping.”

Once Bennett got old enough to go out without his parents, he’d ask his mom to drop him off downtown. That’s how he got involved in the open mikes anchored by beloved mentor “Brother” Mike Hawkins at YouMedia, a teen-focused studio and digital learning space in the Harold Washington Library that’s nurtured countless young poets and rappers. On other trips, he and his crew would end up at Navy Pier, freestyling to each other on its eastern end.

“I grew up in one of the most dangerous neighborhoods in Chicago,” Bennett says. “You have to travel outside of your community. You have to seek to be in a good environment. You have to seek to go outside and hang out with your homies and be in a safe place. You have to decide yourself that you hanging out at Navy Pier is best for you when you’re 13 and 12. That’s what I did.”

Bennett, who now lives in River North, first got into rap in 2005—he saw the video for “Hope,” an inspirational track from the Coach Carter soundtrack by Chicago legend Twista and Bad Boy Records singer Faith Evans. As he grew older and rapping became more than a hobby for him, he began to better understand the dynamics of segregation in his hometown. He knew he wanted to make music that encouraged inner-city kids like him to not feel bound by their circumstances, and he still sees that Twista song as a catalyst.

“It gave me some hope that possibly through anything I did—no matter if I was a janitor, a rapper, a schoolteacher, a lawyer—I could be good at what I wanted to do,” Bennett says. “That’s when I decided that I want to use my words to change the way people perceive the world and perceive the things they can do. Open up their basic idea of what a boundary is for someone that looks like me.”

Last month Bennett released his third EP, Be Yourself, and it’s devoted to that belief. On the six-track tape, he speaks to young people struggling with the pressure to change who they are in order to fit in—social media can make that pressure more intense and harder to avoid, but thankfully it can also help kids find other people who don’t conform. Last year, Bennett came out as bisexual after suppressing it for years, and since then he’s been devoted to unearthing his true self. He has to navigate the strains of toxic masculinity that remain entangled with the public’s ideas about what male rappers are like—hard, tough, violent, with worldviews defined by drugs, gangs, and the pursuit of women.

In July, just before the start of Bennett’s listening party for Be Yourself, his DJ spun Chief Keef’s “Faneto” and encouraged everyone to yell “Fuck 69″—playing into the feud that Brooklyn rapper 6ix9ine has been trying to start with Keef. Bennett walked onstage and told his DJ to stop it—he didn’t want no part of that. His music is about bringing people together, he explained, not fueling 69’s senseless and potentially dangerous antics.

Bennett’s journey as a black man and a rapper extends to his native south side as well. As much as he loves and praises those neighborhoods, those feelings don’t always map comfortably onto reality. For this interview, he wanted to take us to where he’d grown up, but he ended up deciding it’s “not safe.” In an ideal world, the city would provide as many resources for black people on the south and west sides as it does for white people and tourists downtown—and those resources could help build safe and thriving communities.

“That’s why we gotta get a new mayor,” Bennett says. “That’s why these things gotta change, because I shouldn’t have to take y’all downtown. This shouldn’t be life. This shouldn’t be how it is.”  v