CHICAGO — Second City is celebrating its 60th anniversary this year and there is a seemingly endless list of alumni who have gone on to become household names. Many have moved to New York or Los Angeles, but on any given night somewhere in town you can find new and veteran performers knocking audiences back on their heels. Weirdly, Chicago has never been a TV comedy hub.
A few years back there was the low-key but sweet comedy “Shrink” from Second City alum Tim Baltz on NBC’s Seeso, the network’s first and short-lived attempt at a streaming service. There’s the brilliant and wonderfully specific “South Side” on Comedy Central, which was renewed for a second season, although co-creator Bashir Salahuddin didn’t come up through the city’s sketch and improv ranks. In both cases, the creators are based in L.A.
By contrast, the new comedy “Work in Progress” (premiering Sunday on Showtime) comes from longtime improv performers who live and work in Chicago. And the story of how they got their show made is thrillingly atypical.
Abby McEnany and Tim Mason are 20-plus year veterans of the sketch and improv scene — and have been friends for just as long — but in terms of making television, they’re coming in cold. McEnany told me she’d never been on a set before “Work in Progress” — and she’s the star of the show. A richly funny and semi-autobiographical portrait of depression, new love and simply trying to make it through the day in this bizarre world we all inhabit, she plays a “fat, struggling queer dyke” who is forever grumbling about the world’s absurdities.
McEnany and Mason are the show’s creators, but they have also teamed up with a Hollywood veteran in Lilly Wachowski, a Chicagoan herself who, with her sister Lana, made “The Matrix” films, among others. On “Work in Progress,” she is a co-writer and co-showrunner along with McEnany and Mason.
Her involvement with the show brings not only practical experience but lived experience. Abby’s love interest on the show is a trans man, played by trans actor Theo Germaine of Netflix’s “The Politician.”
“To me that was one of the most interesting things about participating in the show,” Wachowski said. “Here’s a person that doesn’t necessarily fit into the tidy binary of the gender spectrum, or the polemic of the gender spectrum. And that was something I could super relate to as a trans woman.” As for Abby’s character, “she’s entering into this younger world, entering into a more trans world and having troubles with a lot of the same issues that trans people have, like in the way that they’re perceived in the bathroom. So yeah, for me it was a huge component to the show and I really wanted to put some oomph into it.”
McEnany and Mason first started working out ideas for the show in 2016, and not long after Mason signed with a manager. “So I was taking all these general meetings that you take out in LA where it’s like, ‘And what else are you working on?’ And I would always talk about this show along with some other stuff that I had, and the reaction was always very weird. Like, we’re going to bring this straight white cis guy in for this? They were like, ‘That sounds interesting, I hope you find a home for that.'”
I wondered if anyone said outright that he might not be the best person to help tell Abby’s story. “Everybody. I said it to myself.”
“And he said that to me,” McEnany said.
Wachowski calls Mason a “great ally and he’s doing his best to amplify voices and that’s what you really need from cis people and straight white guys — listen and amplify marginalized voices. So that’s working out great. And Abby is one of those marginalized voices. It’s criminal that Abby hasn’t ever booked anything. It goes to show you how messed up the entertainment world is.”
McEnany is philosophical: “I don’t fit many roles and I’m a really bad auditioner. So it’s just like, I have to create work for myself.”
McEnany and Mason co-wrote the pilot for “Work in Progress,” which they self-financed and he directed. (He would go on to direct the entire series.)