An hour with the graffiti-artist-turned-painter Hebru Brantley in his Pilsen studio—a large warehouse loft full of cluttered tables piled with spray paint cans, bags of Skittles, and half-finished canvases—feels like a minor lesson in multitasking. In a matter of minutes, the six-foot-eight artist checks the sales numbers on his online store (hebrubrandstore.com), fields phone calls from a Hong Kong collector, and puts the final touches on one of his comic-book-style pop-art paintings. He will later hop on a plane to London, where he has a solo show at the gallery Mead Carney. “It’s a little crazy right now,” says Brantley with a sly smile.

At 33, Brantley is one of Chicago’s fastest-rising artists, with some of his works commanding upward of $100,000 and a rapidly growing collector base that includes entrepreneur Matthew Pritzker and rap impresario Jay Z (who spent $20,000 on a Brantley painting in 2012). In the last year alone, Brantley has had work in 10 gallery shows and was the featured artist for both Chicago Artists Month and Chicago Ideas Week. Now, on June 14, he will premiere nearly 40 new works in Parade Day Rain, a solo show at the Chicago Cultural Center. “It’s a big moment,” he says. “This is my chance to put you in my world.”

Brantley’s Instagram feed depicts a world right out of a Kanye West music video. There are photos of him skateboarding with Lil Wayne, smoking cigars with Carmelo Anthony, and hanging with Lenny Kravitz. In an era when most street artists find fame from the shadows, Brantley has built a brand by broadcasting his ties with America’s glitterati.

Growing up in Bronzeville, he spent most weekends cruising the South Side looking for walls to tag and train cars to mark. “We’d scratch-bomb on trains, tag freight cars—you know, do throw-ups across the city,” Brantley says of the ’90s graffiti scene. “It was all about getting your name up wherever you could.”

He didn’t discover high art until he was 16 and his mother, Pamela Glover, an assistant at Johnson Publishing Company, gave him a book on Jean-Michel Basquiat. “I was entranced by him. It was like looking at the guy who did it first,” says Brantley. “He was a rock star.”

Two years later, in 1999, Brantley headed to Clark Atlanta University to study film. But he quickly soured on the industry (long hours, little creative control), preferring to sneak into art classes at the Art Institute of Atlanta. “I started exploring different things beyond Basquiat. I was honing my own style,” he explains. “It was like a crash course in painting.”

For the next couple of years, Brantley made ends meet working at HMV Records while painting on the side. Then, in 2002, he made his first sale. “My friend [Philadelphia record producer] DJ Drama bought a painting for $800. It was a big confidence boost,” Brantley recalls. “After that, I started thinking about just doing art.”

Today, Brantley’s work, like Basquiat’s, nods to black American history and gritty urban life. But he also brings his own affinities—Marvel comics, hip-hop music—to the canvas. His 2012 piece Captain, O’ My Captain, for example, depicts a black Captain America taking a cigarette break. “The paintings don’t take themselves very seriously,” he says. “I’m a kid at heart. But they still have some of those darker undertones.”

Some of that darkness comes from Brantley’s own life. Five years ago, he lost both his mother and stepfather to cancer within a six-month period. “I wasn’t painting much at that time,” he says. “I had moved back to Chicago to take care of my parents, and I felt drained. But I started to carry a sketchbook. I figured at the very least I could journal what was happening.”

It was during those doctor visits and hospital stays that Brantley began sketching work for a solo show, Fade Resistant, at Three Peas Art Lounge, a now-defunct gallery in the South Loop. “My mom just really wanted to make it to the show, but on the day I was going to take her, she lost vision in one eye and didn’t have the strength to walk,” Brantley says. Though Glover never saw the show, Brantley recalls that she gave him a piece of advice that stuck: “Be shark-like. Always moving, never stopping.”

To hear Brantley tell it, his rapid rise is due as much to his role as a savvy salesman and networker as to his art. “It’s all about growth. I want to do films, heavy licensing deals. I want to run the whole gamut,” he says. “I want people to come out of the shower and step on a Hebru Brantley rug.”

Hebru’s World

Brantley’s work ranges from pop-art paintings to life-size fiberglass figurines.