For decades, the dominant style of comedy coming out of Chicago was sketch. With incubators like Second City and iO, the city had a direct pipeline to Saturday Night Live and SCTV. But recently, thanks to comics who have gone on to TV success, such as T.J. Miller (HBO’s Silicon Valley), Kumail Nanjiani (Silicon Valley, Comedy Central’s The Meltdown with Jonah and Kumail), and Hannibal Buress (Comedy Central’s Broad City), the standup community has drawn the spotlight. On any given night, you can find dozens of performers, ranging from deadpan to deliciously depraved, taking the mike around the city. Meet 16 of Chicago’s best.
Style: Nerdy and literate. Burke is a master of highbrow humor.
Joke: “I’ve developed a look like I could walk into any community college in the country and just start teaching, and no one would call security until it was way too late.”
Dates: October 6 at 100 Proof Comedy at ComedySportz Theatre; October 15 at Comedians You Should Know at Timothy O’Toole’s Pub
Style: Meandering, booze-infused tales of near-death experiences, sharply told with beer in hand.
Joke: “You should always block aside Sunday mornings. Make time for church or, if you’re like me, figuring out which bar has your jacket.”
Dates: Flannery hosts The Blackout Diaries at venues around town. Go to blackoutdiaries.info for more information.
Style: Painfully revealing, with the intensity of a rodeo bull.
Joke: “A man once told me, ‘If you know another man is attractive, that means you’re gay.’ That can’t always be true. I know a man is attractive because the moment I see him, I hate him.”
Dates: October 20 at Stiff Investigations at Hungry Brain
Style: Adolescent. This Indiana native has an arsenal of sex jokes, but he’s not afraid to delve into his dark side, as evidenced in his Wrestling with Depression podcast.
Joke: “The scariest neighborhood in Chicago is Wrigleyville. I’d rather go to 47th and King with a sandwich board that says the ‘N’ word all over it. Wrigleyville on a Friday or Saturday night is like the apocalypse is being sponsored by Axe body spray.”
Dates: October 5 to 7 at the Improv in Schaumburg
Style: Ferocious, reckless, and unfettered. This Humboldt Park comic—whose bits are bizarre, dark, and often disturbing—is an oddball force of nature.
Joke: “I burn bridges, but I don’t call it burning bridges. I call it me being right again.”
Dates: October 30 at Reggies Rock Club; October 31 at the WIP Theater
Style: Deeply personal. White swings like a prizefighter, going in for the comedy kill with jokes that look misery straight in the eye.
Joke: “My family passed away one by one over a period of two years. Don’t worry though, I’m looking at life in a casket half full kinda way.”
Dates: October 7 at Hoo Ha! Comedy at Rockit Burger Bar
Style: Self-deprecating. The South Bend–born comedian takes one swipe after another at her own bad decisions, including one-night stands, drugs, and her Patsy Cline cover band.
Joke: “I want to be a stepmom, which is just like a regular mom but with a tighter vagina.”
Dates: October 3 to 4 at the Comedy Bar; October 14 at Chicago Underground Comedy
Style: Adolescent. You might think smartly written penis humor is an oxymoron, but Lebovitz nails it with a twinkle in his eye and a twirl of his mustache.
Joke: “My vision board is just a picture of a bathroom large enough to take a dump in with the door closed.”
Dates: October 23 to 25 at Timothy O’Toole’s Pub; November 11 to 16 at Zanies
Style: Cheeky. The Humboldt Park siblings have become scene stalwarts thanks to their wicked banter about bad jobs, bad sex, and great imbibing.
Joke: “I want to thank Jim Beam for being the only man I trust inside of me.”
Dates: The Puterbaugh Sisters host the comedy showcase Entertaining Julia every Sunday at the Town Hall Pub.
Style: Bizarre. A native of California’s Inland Empire, Abramson delights in nonsensical one-liners, time-bending pranks, and lots of tomfoolery.
Joke: “I swallowed my pride, and now I’m worried an ego is growing inside of me.”
Dates: September 26 at the Lincoln Lodge
Style: Pithy. Barnes—who often describes himself as an African American hailing from African America—has a penchant for puns and rapid-fire one-liners.
Joke: “I love diversity. Is she black?”
Dates: October 26 at Cole’s Bar; November 20 at Hungry Brain
Style: Goofy. This lanky Logan Square comic doesn’t shy from the outlandish and often uses slapstick and props in her routine.
Joke: “I play a drinking game called Never Have I Ever. Drink a Zima if you’ve done what I’m about to say: Never have I ever been broken up with because I farted on someone during the movie The Notebook.”
Dates: October 7 at Hoo Ha! Comedy at Rockit Burger Bar; October 14 at Lincoln Hall
Style: Cheerfully insulting. The self-described Prince of Bronzeville pokes fun at everyone from hipsters to the homeless.
Joke: “I don’t like it when black people wear colored contact lenses; they look like ThunderCats.”
Dates: November 1 at the Nasty Show at the Laugh Factory
Style: Blue-collar. Always a formidable presence, Kallas built a cult following with his wry wisecracks and trademark slouch.
Joke: “Every few months I like looking through my ex-wife’s Facebook pictures to see how ugly my kids got.”
Dates: October 1 and 22 and November 12 at Comedians You Should Know at Timothy O’Toole’s Pub
Style: Old-school. The Beverly comedian pulls his ammo straight from dad’s joke book.
Joke: “I’m not a fan of birth announcements: ‘It’s a girl, eight pounds, 12 ounces.’ What are you supposed to do with that information? What, did you catch a fish? I always send a note back: ‘Congratulations; Love, Pat; six feet, one inch, 185
Dates: November 12, 13, 21, and 26 at Zanies in Rosemont
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