For Abby McEnany, timing is a funny thing. In certain ways, she’s always been precocious: she had her first panic attack at age five and was in therapy by eighth grade. In other ways she’s more of a late bloomer: she finished college at 24 and her professional comedy career began in earnest at 40, when she joined the touring company of Chicago’s Second City theater. She was 51 when Showtime greenlit her autobiographical TV series Work in Progress.
McEnany, who still lives in Chicago, knows hers is different from most show business stories, and that’s OK with her—she’s always felt a little bit different. If she’d gotten Work in Progress any sooner, “it wouldn’t have been the right time,” says the University of Chicago alum. “When I say I take a long time to get stuff, I’m not putting myself down. It’s just how my brain goes and how I need to get there.”
In Work in Progress, McEnany, AB’92, stars as: Abby McEnany. The first season follows Abby—the character—a self-described “fat queer dyke” living in Chicago, through a mental health crisis and a new relationship with a trans man two decades her junior. The second season, which aired this past fall, finds Abby weathering the COVID-19 pandemic, grappling with racism and white supremacy after the murder of George Floyd, and trying, inch by inch, to grow.
Despite all of the above, Work in Progress is very much a comedy, if an atypical one. There are jokes: “I look like Mitt Romney Jr.,” middle-aged Abby laments at an ultracool queer nightclub. “Junior?” her love interest teases. There are classic sitcom premises: Can Abby and her friend survive multiple family gatherings in one day? There are cameos: “Weird Al” Yankovic appears as the sangria-loving husband of Saturday Night Live alum Julia Sweeney, playing herself, prompting many a “wait, are they?” Google search. (They are not married in real life.)
The series takes big swings, freely mixing pathos, hopefulness, and pratfalls to create a singularly oddball tone. Abby is both the show’s protagonist and its punching bag, a figure whose often-in-error-never-in-doubt pomposity sits alongside her vulnerability and kindness. In one of many positive reviews, Emily Nussbaum of The New Yorker praised the show’s “distinctive, salty vibe, driven by McEnany’s simultaneously self-loathing and self-aggrandizing swagger.”
Talking to McEnany, it’s easy to see how her particular brain produced something at once so tender and so bonkers. She is thoughtful, warm, and effusive, prone to self-deprecating asides and long tangents punctuated by big, throaty laughs. Mid-tirade on the horrors of social media, which she does not use, she catches herself: “Autonomy and anonymity—those two things are so beautiful. I don’t understand this culture that we live in! [Pause.] Wow, is she ranting about social media again? Yaassssss! Damn. Anyway.”
By writing a show about someone who feels different and flawed, McEnany discovered how many other people feel different and flawed too. Not long ago McEnany was out with friends when a stranger came up to her and announced, “I’m an imperfect queer too!” Another time she was recognized on the street while openly weeping. “I was like, ‘Hey, I’m so sorry I’m crying, I just had therapy,’ and they were like, ‘So did I!’”