We poke fun at Chicago’s desperate thirst for a celebrity culture, so desperate that anyone remotely notable who was born in the city or started a career here or graduated from an area university is forever celebrated as a local hero. Hannibal Buress, meanwhile, has a legitimate claim to local-boy-done-good status. The 34-year-old comedian, a regular on Comedy Central’s Broad City, previously lived in New York but returned earlier this year to the city of his birth. He was raised on the west side and paid his dues in the mid-aughts hustling between three to four stand-up shows a night. He stood out with absurd observational humor delivered with a mix of confidence and indifference. He confessed in an old joke, for instance, that he keeps jars of pickle juice in his refrigerator to “flick on my sandwiches for flavor.” Buress still makes a habit of dropping into small rooms around town—the open-mike night at Cole’s, the Paper Machete at the Green Mill—but these days the majority of his gigs are high profile. He opened for one of his comedy heroes, Chris Rock, at the Chicago Theatre last September, and on December 29, he’ll headline a show at the Civic Opera House. Last year, he launched a podcast, Handsome Rambler, on which he chronicles stories from the road and interviews guests such as Chance the Rapper. Buress, like Chance, has taken an active interest in giving back to his hometown; he’s in the early stages of planning a small community center on the west side that offers comedy classes and other opportunities for youth. We asked him about that project, his formative years in Chicago, and his fraught relationship with The Cosby Show. (And no, Buress doesn’t talk about his arrest in Miami on a disorderly intoxication charge; this interview was conducted nearly two weeks prior to that incident.)

You grew up on the west side.

Yeah, I rent it out when I’m not there. I don’t have possessions there, pictures of family and stuff, old CD collections—it doesn’t have that type of personality.

How do you juggle Airbnb while you’re on the road?

Southern Illinois University, Carbondale, Illinois. Dick Gregory went there. Who else? Open Mike Eagle, Tony Trimm. I went to college for four years, then stayed with my parents for a couple years after. I went to New York for a few months in 2006, then came back.

What was your performance schedule like in Chicago?