The opening scene of new comedy series Work in Progress sees Abby McEnany trying to bring back “wassup”. The second sees her announcing her potentially imminent suicide to her therapist: “I’m gonna kill myself in 180 days, if things don’t get better.”

Work in Progress is not only McEnany’s first TV series but it’s the first time she’s been on a professional set. And with this original, melancholic comedy, she is setting the bar high. Its autobiographical traits – McEnany plays “Abby”, and is a self-described “fat, queer dyke” – are nothing compared with its origins story, which is something out of a fairytale.

“That’s funny, because I often say that it’s like a fairytale. It is legitimately my dream come true,” says McEnany, calling from her Chicago apartment. At 51, she is the star, co-creator and co-writer of Work in Progress, which is quite the first TV gig. She is out of coffee, and warns me that some may be delivered as we speak. “I’m so embarrassed, dude! What an asshole move.” Clearly, success has gone to her head. “I mean honestly,” she laughs. “What a bougie bitch!”

McEnany moved to Chicago for college in 1986, and has been a mainstay of the city’s improv and sketch comedy scene for years, eventually joining Second City’s touring company when she was 40. Three years ago, she started a form of live storytelling at the iO Theatre, performing material she had written about her life. She called it Work in Progress. Her friend and co-creator Tim Mason was looking for material to direct, to build up his directing portfolio, saw the show, and suggested they work together on bringing it to screen.

“That’s what I’d always wanted to do. I’m better at working with people. It helps me not get anxious. All that negative talk, that fatalism, that defeatism, is so easy when you’re by yourself. Hold on.” The coffee arrives. “I’m such a jerk! Anyway. I’ve always wanted to do it, because I think there are not a lot of people like me in film or on TV.” She does believe there are more and more different kinds of women on screen. She loves Orange Is the New Black, for example. “You see fat women and old women and queer women and butch women. That’s who I am, right? Old, fat, butch, grey-haired. I’m not trying to say I’m the only one. But I would say, there are not a lot.”

Before Work In Progress became a series, she would go to auditions (she says she was “horrible” at it), but never booked a job. “They’re not like, you can play a mom and sell fast food. They don’t want to show fat people eating burgers. And that’s in commercials. In TV shows, there’s not a ton of people that are not the palatable people that America wants to look at.” She mentions a joke she has with her friends. “When guys dream of lesbians, they’re not thinking of me,” she laughs. The solution to her “abysmal” history of auditioning turned out to be right there in front of her. “That’s why I thought, I’ve got to write for myself.”

McEnany and Mason were considering turning their idea into a web series, but the pilot they had put together caused waves at Sundance in 2018; it was picked up for a full series by Showtime, and The Matrix co-creator Lilly Wachowski, whom McEnany had known for a few years, effectively came out of retirement to produce and co-write. The pieces had all fallen into place. “Sometimes Tim and I will be like, how did this happen?” she says. “To have this amazing opportunity at 51 years old is just beautiful. I can’t believe it.”

Then again, she reasons, it takes her time to build up the confidence in whatever it is she is doing. “When I had my first real relationship, I was 29.” She auditioned for Second City’s touring company for 10 years before she got in. “It’s just one of those things. I believe this wouldn’t have happened in my 20s. It wouldn’t have happened in my 40s.” Much of the story of Work in Progress is about Abby, the character, finding opportunities to live, when she has just about given up hope. “I think the story is really based on my life.”

What everybody wants to know, of course, is how much of it is true. “Now, my answer is, it depends what time of day it is, and who’s asking,” McEnany laughs. “Everyone has terrible moments, I’m a human being, but I hope I’m not as terrible.”

Instead, the truth comes from what she calls the “messiness” of Abby. “I have mental illness, I struggle with a bunch of stuff, I try to be an honest person and open, but it’s scary. The character’s been beaten down and has sworn off relationships and is struggling. I’ve had times in my life where I’m so depressed and stuck.” Her parents first took her to therapy when she was in eighth grade. “I had my first panic attack at five, and you don’t have the words at five. When I started exhibiting OCD, it wasn’t really in the lexicon like it is now. I was able to talk to my parents and they had the means for me to try therapy.” She considers herself lucky that they were able to give her the care she needed.

Abby McEnany’s romance with Chris, played by Theo Germaine, in Work in Progress is based on real life. Photograph: Adrian S Burrows/Showtime

Comedy, she says, was everything. “It might sound hyperbolic, and I haven’t had much coffee, but humour has saved my life, I think.” Just before McEnany joined Second City, her mother died, following a long illness. “Humour has gotten me through some really hard times. Some of the funniest moments that I’ve had with my family are in that horrible three and a half years that my mom was dying. There was weirdly a lot of healing in that time.”

Work In Progress is a deft blend of wry pessimism and tenderness, particularly in its central love story between Abby and a younger trans man, Chris (The Politician’s Theo Germaine). “It’s based on a real-life romance that I had. I was actually just talking with my ex this morning, and they’re coming to the premiere here in Chicago,” she explains. As the couple’s relationship begins, Chris takes Abby to a queer party. “When I was writing it, I was like, this can be a queer wonderland. There’s gonna be performances, art, sex toys, leather, and it’s going to be this wonderful coming together of queerness and diversity and openness and expression. I define myself as a person as a sex-positive prude,” she laughs. “And this is such an opening of the character’s eyes. Her whole life is opening up and other opportunities are coming to the fore, and Chris is the vehicle for that, for sure.”

Elsewhere, Saturday Night Live alumnus Julia Sweeney has a recurring role as herself. In the early 90s, Sweeney created the androgynous SNL character, Pat, largely based on the gag that nobody knew Pat’s gender. “One of my stories in that storytelling show was that Julia Sweeney’s Pat made my life a living hell,” McEnany says. “I was starting to wear a lot of overalls, I was masculine, big, fat – my weight fluctuates a lot – and people would be calling me Pat. And if you’re called Pat, nobody’s giving you a compliment.” She remembers being in a lesbian bar in the late 90s, being called Pat. “It’s like, wow, this is supposed to be a safe space and I’m being judged for what I look like? It’s hateful. Where do I get a break? It really defeated me.”

‘I think the story is really based on my life,’ says Abyy McEnany of Work in Progress. Photograph: Courtesy of SHOWTIME/Showtime

When the fictional Abby runs into Julia Sweeney in a bar, the shock of finally confronting her nemesis after so many years causes her to pass out. The real Julia Sweeney used to live in Chicago, and McEnany and Mason reached out to her through a mutual friend. “She was so supportive, she was on board from the very beginning. And she’s been such a genuine joy,” she says. Did it give her chance to readdress Pat herself? “I think so. I love her openness about it. She had an opportunity, and we had an opportunity.” In fact, they got on so well that when they were unsure whether Work in Progress would be picked up, Sweeney invited McEnany to live with her in Los Angeles. “I cannot tell you how much I love her.”

Like McEnany, Work in Progress is a true original, and it marks the arrival of an important new voice. But there is one question left to answer. How close is she to bringing back “wassup?” “Oh man! I’ve been working on that for about 10 years,” she says, laughing. “I would say I’ll start a change.org petition to get that back. But I haven’t started it yet.”