Abby McEnany in Work in Progress Credit: Jean Whiteside/SHOWTIME

A chance meeting at the corner of Clark and Winnemac. A one-woman show at iO Theater. A viral short film filled with local improvisers. In an alchemic combination, these quintessential Chicago events catapulted prolific Chicago comedian Abby McEnany into the national spotlight.

McEnany, a 51-year-old Chicago improviser, makes her television debut this week on Showtime’s Work in Progress, a half-hour, single-cam comedy cocreated by McEnany and Second City alum Tim Mason, and cowritten by Lilly Wachowski (The Matrix, Sense8). Her path to success is not a story of a meteoric rise in the second half of a long career in comedy—”career” being a strong word, in McEnany’s opinion. Her path to this premiere is a story of Chicago, its small-town connections, and a growing movement to give our city and its artists a second look.

I reviewed McEnany’s autobiographical storytelling show of the same title at iO in 2016 and was charmed by the “voyeuristic trip” into the self-labeled queer dyke’s “mile-a-minute brain.” Mason, a film director and longtime friend of McEnany, saw the same iO show and suggested a film adaptation over coffee at the Andersonville Starbucks. An attempt at a webseries morphed into a pilot filmed on a shoestring budget and in-kind donations from the improv community, which gained Showtime’s attention at this year’s Sundance Film Festival. After meeting McEnany several years ago outside Andersonville Hardware Store, Wachowski kept her eye on the project as well. She, coincidentally, is managed by the same team as Mason, who was signed in 2017 after the success of his short film No Other Way to Say It, and these bubbles of connection and conversation resulted in Wachowski and Circle of Confusion signing on as executive producers. “It’s just a very strange, long story about kismet and shit coming together,” McEnany says.

Adapting her stage material for television took some reimagining, but a narrative quickly centered on Abby’s transformative relationship with a transgender man, something McEnany had personally experienced but didn’t talk about in her stage show. It took Wachowski to remind her that these stories were more than just her life; putting them on television is a big deal.

“To have a love story with trans characters . . . the fact that this fat, gray-haired woman who is a queer dyke as the lead of a fucking Showtime show, that is revolutionary,” McEnany says. The weight of their endeavor carried through the casting in a concerted effort to populate the characters of the whole show with queers, from baristas to Lyft drivers to bartenders. In a broad casting call to queer, nonbinary, and transgender Chicagoans—no performance experience necessary—McEnany, Wachowski, and their casting director held personal interviews, adjusting character pronouns as needed.

For Mason, who identifies as straight, white, and cisgender, and directed every episode of season one, it was not only a learning process but an education in privilege. “From the way our language is oriented to how our bathrooms are oriented, how much the world is designed for people like me and so many things that I take for granted,” Mason says. “The education is to try to be understanding of how many struggles are happening that I don’t even see and help bring them to light.”

McEnany says the unexpected benefit of pulling material from her life was that “for once I actually felt like an expert,” in relation to her role as the writers’ room muse. Her ability to be vulnerable at such high stakes is a credit to years of processing both in therapy and in her one-woman shows, as well as the writers’ room’s healthy respect for her clear personal boundaries. And it’s also a character, McEnany reminds herself, finding safety in the fictionalization.

A mix of McEnany’s storytelling and Mason’s introspective gaze, Work in Progress‘s tone is wacky and morbid, clever and cuttingly real. “As a depressed person, comedy has saved my life,” McEnany says. “I worry that might sound dramatic, but it’s true.” Costar and local actor Karin Anglin, who plays Abby’s sister, Alison, says these “lovely, self-deprecating elbow-in-the-gut” lines drew her to the project. (In another Chicago connection, Anglin and Mason knew each other from playing husband and wife on a long-running Giant Eagle supermarket voice-over campaign.)

Theo Germaine and Abby McEnany in Work in ProgressCredit: Jean Whiteside/SHOWTIME

Among subplots addressing mental illness, suicidal ideation, and sizeism head-on, moments of hilarity emerge, from a therapist dying midsession to a bitchy coworker buying Abby a large, plot-critical tub of almonds. Her relationship with transgender man Chris (The Politician‘s Theo Germaine) takes her own self-examination to a deeper level, opening Abby’s eyes to today’s “queer wonderland,” nothing like her “very white and cis coming-out experience.” Chris thrives on new experiences and confrontation, in one instance bringing Abby face-to-face with her nemesis, Saturday Night Live alum Julia Sweeney, whose character “Pat” caused her nothing but emotional pain. In another, Abby faces her puritanical sexual views at a sex-positive party.

“I have to be very aware of my privilege,” McEnany says, as a white, cis, queer person in an urban community. The pilot lacks people of color by design, she says, to illustrate how Chris’s world of diverse races, identities, and sexualities forces Abby to reckon with her internalized racism and homophobia.

Work in Progress was conceived, written, cast, produced, and postproduced in Chicago, a rarity for television—in fact, this is the first project from a major studio with a network release to do so. It’s a reflection of the cocreators’ vision and Wachowski’s advocacy.

“I love that we’re letting Chicago represent itself as a creative, thriving center for film and the arts,” Mason says. The show overturns well-worn imagery like scenes at the Bean and conversations beneath the el tracks. From the Andersonville businesses that benefited from the 35-day shoot to the local cast that walked away with coveted SAG cards, Anglin says the show is a testament to the “camaraderie, grit, and work ethic” that she finds unique to the Chicago film industry. In McEnany’s 2016 one-woman show she gave the disclaimer, “what happens here stays here.” Thankfully, for the rest of the world, she’s ready to share her story and her Chicago. v