Chicago comedy writers make strides in TV and film

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

It’s a neat feeling, watching something like Comedy Central’s Workaholics and recognizing Maribeth Monroe from her great work at Second City, or knowing Sonic’s slush cup runneth over with the improvised talents of TJ Jagodowski and Peter Grosz in its commercials. We’re understandably proud of our hometown talent and like seeing them excel beyond Chicago’s urban sprawl. A recent wave of hires, originating from both coasts, has put the attention behind the camera as well: These five Chicago-trained comedy writers are making a name for themselves in bylines and executive producer credits, ensuring we’re one step closer to taking over all of Hollywood.

1/5

Katie Rich

Katie Rich is always the smartest person in the room. Not the kind of smart where she’d rub it in anyone’s face by saying things like “Did you read that article in the Times?” But the kind of smart where she’ll perfectly articulate something that’s been bothering you for days, and be glad to have helped. Once for Write Club, a literary bout in which two writers are given broad topics (life vs. death, etc.) to defend, Rich found a way to spin “rock” into a shameful admission of loneliness and a complicated push-pull between her desires to either spit in the face of wedding culture or conform, all in like, six-and-a-half minutes. That kind of smart.

It’s no surprise, then, that Rich was plucked off of Second City Mainstage in late November 2013, in the middle of her third revue, to work on Saturday Night Live as one of the “Weekend Update” writers. It’s exactly the kind of job that requires political savviness (which Rich exhibited in newsy pieces for The Paper Machete) and the ability to make complicated ideas seem simple. Their moving target is Rich’s sweet spot.

Still, it’s a lotta work. Rich is required to write 30 jokes a day, and in the end she and the rest of the posse cut it down from 600 jokes to 12. This is where her training kicks in. “At Second City, you take material you wrote that day, put it up in front of an audience that night, and the feedback is immediate and you can't argue with it,” she says. (You know, like “You suck!” or whatever.) “So I've been able to come into SNL and write quickly and often without becoming too precious and attached to my writing.”

She’s also in good company: SNL boasts the additional hometown pride of Aidy Bryant, Vanessa Bayer, Michael Patrick O’Brien, Tim Robinson and “Update” coanchor Cecily Strong. It’s nice to score another one in the “win” column, especially someone who’s exactly the kind of smart Katie Rich is.

CORRECTION: A previous version of this piece incorrectly stated that Rich had been a castmember of Whirled News Tonight. We regret the error.

2/5

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.”

3/5

Kay Cannon

“All I ever want to do is watch television, nonstop, for hours and hours.”

It’s a miracle Kay Cannon ever gets anything done, yet her writing resume reads like the kind of thing a Level One iO student might journal about under “dream career.” She worked for six years on 30 Rock, two on New Girl, wrote the script for 2012’s Pitch Perfect and is currently hunkering down to finish its sequel. (Pitch Perfect is like if Mean Girls was set on a college campus with a cappella; Tina Fey’s force is strong with this one.)

Her love of television—and the obsessive consumption thereof—has actually motivated Cannon. Early on she decided to write with her TV paused on the Bravo network, only taking a break when the DVR unpaused itself and only then watching just enough to catch up with the live feed. It’s a dirty system, but it works.

Writing wasn’t always in the cards for Cannon. She trained in Chicago at pretty much every theater before she was hired by ComedySportz, her first paid gig as an improviser. Later she would find her way to Amsterdam with Boom Chicago before winding up in New York, thinking of herself as a performer first. She was unemployed for two years before getting the job writing for 30 Rock.

The lessons Cannon learned as a performer still apply on the page. She makes sure characters never ask questions and enjoy being around each other—the basic building blocks of any good improv show. “I’m constantly asking myself, ‘How is this character funny?’ ” she says. “When I feel like something is too hard or not coming easily, the scene is usually not right.” Both 30 Rock and New Girl are packed with jokes, so Cannon’s diligence is a perfect prerequisite for turning in tight scripts.

It may not have been her first love, but Cannon is smitten with the writing process, and reminds herself every chance she gets—this infatuation has become motivating in and of itself, too, so the TV remains mostly off. “I tell myself, before I start writing, that I get to do this,” she says. “I can remember a time when I was jobless and that person would have killed to have had a deadline.”

4/5

Sarah Haskins

Sarah Haskins performed in the mid 2000s with American Dream, a fabulous and innovative team that would create an entirely new improv form whenever they went on stage. Once a member brought a bag of old clothes to inspire scenes; another time they staged a fake reunion spectacular even though they performed weekly. Naturally, nonconventional groups attract nonconventional comics—a.k.a. opinionated comics.

“It certainly prepared me for getting a lot of input from a lot of people all the time,” Haskins says with a laugh. That skill comes in handy for her work as co-creator and showrunner of Trophy Wife, a freshman ABC sitcom with decent eyeballs, solid critical backing and the charm of actors like Malin Akerman and Bradley Whitford.

There are at least a million more cooks in the kitchen on network TV vs. the stage at the Playground Theater, and Haskins, 34, has always welcomed the chaos. She moved to Los Angeles in 2007 to work for the scrappy Current.TV and carved out a place for herself on the news show, InfoMania, as a sort of “female correspondent” before that was a bit on The Daily Show. Her “Target: Women” segments mocked the media’s flippant portrayal of women as yogurt-obsessed housewives. But her interests in fiction led her to partner up with cowriter Emily Halpern to pen the short film DILF and now Trophy Wife.

Being surrounded by other hopefuls didn’t deter Haskins. “There are, like, 50,000 people writing screenplays in Los Angeles, so I figured I’ve got as good of a shot as any of them,” she says. “The good thing is I’m naive and a dumb optimist.”

The plot of Trophy Wife is loosely based on her life—a young woman marries an older man with two ex-wives and kids from the previous marriages—but she says some of the best ideas come from Halpern, the other writers, and the network. “We’ve all heard horror stories where an executive comes in and says, ‘This isn’t taking place in a diner, it’s a cop station, and everyone’s an alien.’ That’s not the reality.” she says. “You’re working with human beings, and if they are giving you some critique, there’s something they didn’t get, and your job as a writer is to help them get it. Embrace the revision.”

Photograph: Erika Dufour
5/5

Tanya Saracho

Tanya Saracho talks a lot, and very excitedly, about toilets. That glorious ivory chalice of numbers both one and two has become the symbolic representation of her recent success and unfortunate detours along the way. Yeah, the place where people shit is partially responsible for landing jobs writing for Devious Maids, Looking (she cowrote the first-season finale) and now a gig with the show nobody is talking about, Girls.

“Toilets are my process,” she says with a hearty laugh. It's a process that began 15 years ago in Chicago. In 1999, Saracho moved to the city and was surprised to learn that roles for Latino actors were severely limited; she auditioned for more parts named “Maria” and “Aurora” than she can even recall. She cofounded Teatro Luna as a place to foster Latina theater and offer meatier roles to Chicago’s talented, previously pigeonholed actors. For a decade she ran it “Chicago-style,” as she calls it: running the box office, acting, directing, taking out the trash, and of course scrubbing toilets.

When Saracho first broke into the Los Angeles system—an agent had gotten ahold of her play Mala Hierba, about the trophy wife of a drug lord, and helped with the move out West—she was surprised to learn things weren’t quite as egalitarian. “Everyone has different titles but are doing similar things, and in some rooms you have to act your title,” she says. “On the first day people were like, ‘Wait, you’re a playwright? You skipped being an assistant? You know you’re the diversity hire, right?’ When you’re told that on the first week at work, you’re gonna cry in the bathroom.”

Thankfully, there is little toilet time at Looking and Girls, where talent comes before demographic quotas and Saracho says the process is far more collaborative. HBO has been kind to her, and she's now adapting Mala Hierba as a series for the network, bringing things full circle. Saracho got to this point through gumption and humility. She did all of the theater jobs, happily, and doesn’t seem like the kind of person who loses steam easily.

“At one point when I had more success in regional theaters, I’d go to [the performances] and still start fixing chairs,” she says. “They’d say, ‘You don’t have to do that,’ and I’d be like, ‘Well, I can.’ ” Saracho may find herself doing glamorous work, but there will always be toilets to clean.

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