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Chicago's Men of the Moment

By Tate Gunnerson, Sarah Ryan, Jessie Sardina, Lisa Shames and David Zivan

Photography by Quinn Wharton


From a self-taught artist whose iconic work has been exhibited all over the world to a real estate entrepreneur moonlighting as a TV show co-host, the men of Chicago are having a big moment. Here, five trailblazers sound off—in their own words.

Whether he’s rubbing shoulders with high-brow collectors or hip-hop giants, street artist-turned-fine art painter Hebru Brantley continues to solidify his stance as one of the city’s leading creative luminaries.

“My whole life, I’ve been drawing, sketching and painting. I’m self-taught. I didn’t have an arts education, but I used to sneak into friends’ painting classes in college. I grew up in the Bronzeville area, and my work is inspired by that experience. A lot of people know me for my character Flyboy. There’s a giant mural of him in the South Loop, and last year I animated Chance the Rapper with Flyboy’s goggles for his “Angels” music video. I just exhibited at Art Basel Miami this year, and had my second solo show at Vertical Gallery in Ukrainian Village. I’ve also been lucky to do some pretty cool collaborations with Nike, Lacoste, Hublot and even Garrett Popcorn. Yeah, I’m always working. It’s hard to be an artist. If I was a person who played it safe, I wouldn’t be an artist. I’d be a desk clerk or some shit where I could sit and draw all day. But there’s kind of a void I have to fill. Every day I have to make something. I keep wanting to do more, bigger, on a larger stage. I want to continue to elevate from a career standpoint and a creative standpoint, and to just keep making dope shit.” 

Shot on Location at Hebru Brantley’s Studio