Chicago comedy writers make strides in TV and film

These five Chicago-trained comedy writers are invading airwaves with Windy City wit

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Conner O'Malley

Conner O'Malley


Conner O’Malley, a writer on the new Late Night with Seth Meyers, had things roughly mapped out. In the summer of 2012, he’d auditioned for the Second City Touring Company and his girlfriend, Aidy Bryant, was on one of the theater’s resident stages. Chicago seemed like the place O’Malley would remain, at least for a while (he was also born and raised in the city).

Then Saturday Night Live came a-callin’ for Bryant, and O’Malley made the move out East with her.

The trek was a surprise, but in hindsight it was exactly the right time for him to branch away from the Midwest’s beer-koozie confines. “It’s like when you send a rocket to the moon—if you hit it perfectly, the moon’s gravity will pull you around for the other half of the journey,” he says. “I feel like I had enough inertia to get to that point, and I didn’t realize it.”

It might be due to O’Malley’s ease with absurd comedy, which made him a rock star at the Annoyance Theatre. He appeared in more than 20 scripted shows at that theater, each one narratively kinda weird. He was also a regular at Grabass, the theater’s joke-driven sketch show, and he created an outlet for solo character comedy in the weekly showcase Holy Fuck.

“All those narratives are basically screenplays,” he says about the longer Annoyance shows. And the kinds of rapid-fire bits he writes on Late Night? “That’s Grabass and Holy Fuck.”

It took O’Malley a year to realize he had that skill set. Before that, he walked dogs, and occasionally worked on characters whose desperation was only outweighed by their imaginativeness. He played a community-college coaster from Staten Island who’s written an awful Entourage spec script that he reads with blind optimism, and the mayor of Milwaukee who has been attacked by Shrek in the woods. These circuitous narratives landed him a spot at last year’s Just For Laughs festival in Montreal, where Late Night producers caught his act. (He made his onscreen debut last week, in character as a wild Seth Meyers from a dark timeline two weeks into the future).

“People, myself included, have this desire to unlock the secret of comedy, but I think it’s just having a strong voice. The people who submit crazy packets [to shows] are the ones who get hired,” he says. “It’s better that the world finds a place for you than to try and force your way into something.”

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