Maggie Winters may be an actress and comedian, but, before anything else, she’s a Chicagoan. She has traveled extensively as a performer; her solo comedy tours have taken her from Portland to New York to Edinburgh, and, as an actress, she relocated to Charleston, South Carolina, to film a recurring role on HBO’s “The Righteous Gemstones.”
But her home will always be here. So it’s no surprise that her first filmed comedy special, “Marguerite,” is heavily inspired by her years on the city’s South Side. Over the course of the show’s 60 minutes, Winters takes us on a journey through her life, which began and remains in Beverly.
Despite regularly performing in Los Angeles and New York, Winters feels no pull to move to either coast. “I really have been an advocate for staying in Chicago,” she said. “After the pandemic, the industry changed, and we don’t really have to be anywhere.”
Winters exemplifies this change in the comedy tides. She began her comedy career as an improviser, training at iO and Second City before moving online during the pandemic. Since then, her following has boomed. More than 144,000 users (combined) follow her on TikTok and Instagram, where she can be found with the handle @SaggieSplinters. She hosts the podcast “Literally Life Changing with Maggie Winters,” has appeared on Bowen Yang and Matt Rogers’ podcast “Las Culturistas,” and was recently seen as a bartender on “Watch What Happens Live! with Andy Cohen.”
But “Marguerite” is her first filmed special. She developed the show over two years, with the earliest iteration appearing on stage here in Chicago at Sleeping Village in March 2023. After that, she toured the show across the United States before taking it to the Edinburgh Festival Fringe in the summer of 2024.
“It’s wonderful,” she said of the Edinburgh festival, “but also insanely difficult.”
Artists at the Fringe are in charge of all their own promo, meaning Winters spent the entirety of her month-long run doing her best to convince a crowd of foreigners to see her late-night, one-woman show. Some nights, she was successful; other nights, she performed “to four Scottish people that definitely hated me.”
But no matter how many people saw that version of the show — and how angry or not they were when watching — Winters always had a larger audience in mind. Before leaving for the festival, Abso Lutely Productions, the Los Angeles company behind “Tim and Eric Awesome Show, Great Job!” and “Nathan for You,” had expressed interest.
After a 2025 test filming at Color Club in Chicago, production moved to the UCB Theatre in Los Angeles, a comedy company that has its roots in co-founder Amy Poehler’s time in Chicago.
When “Marguerite” took to the stage there last February, Maggie wasn’t the only Winters calling shots for the show. The production was directed by her brothers, Bart and Liam. The Winters brothers are both artists in their own right; they play together in the local band Melkbelly, and Liam has worked as a union set decorator for Chicago film and television productions. The trio has made videos before for Maggie, but this special is the largest production they’ve embarked on as a group.
“We never did anything beyond videos for ourselves,” Bart said, “so it was fun to be able to jump on Maggie’s coattails to do some of this stuff — even if she didn’t want it.”
But Maggie very much did want it. She worked together with her brothers on the script, bouncing jokes and set-ups off them to see what would work and what wouldn’t.
“I knew they wouldn’t lie to me,” she said. If a bit was working, Maggie was certain her brothers would encourage her to further develop it. But if it’s not?
“They’re not afraid to be like, ‘Hell no.’”
All three Winters siblings are careful not to call the show a “stand-up special.” They prefer “solo show,” a choice taken from Maggie’s time in the improv and sketch scene, where solo shows are created to showcase the variety of a performer’s talents.
And “variety” is the ideal word to describe “Marguerite.” Part “Pee-wee’s Playhouse,” part public access television program, the special begins with Winters asleep in a fantasy version of her own bedroom until she wakes up, several snooze-button pushes later, running late to her own production. A voice-over of her interior monologue offers such helpful instructions as, “Stop staring at the person in the front row!” Winters introduces herself to the audience via slideshow and video sketches are peppered throughout the proceedings.
Yet viewers never lose the sense of community that anchors Winters to Chicago. Though she is open to traveling wherever a production may take her, she says that “being close to my family is really important to me.”
That bond is clearest on St. Patrick’s Day — which, fittingly for a member of a South Side Irish family, is when her special premieres (watch at ucbcomedy.com). For the last 25 years, the Winters family has hosted a St. Patrick’s Day party at home on the day of the South Side Irish Parade. The event is filled with what Winters describes in the show as the “party essentials”: an on-site morning mass (led by her own uncle, a priest); babies (the noisier, the better); and, perhaps most importantly, a port-a-potty in the garage.
In a huge white tent, bedecked with both Irish and American flags, row after row of green-draped guests gathered around tables to pass drinks back and forth, eat corned beef sandwiches and laugh. As Winters moved throughout the proceedings — from the tent to the furnished basement to the kitchen — the topic of her exploits, and particularly her upcoming special, returned to conversation after conversation. Downstairs, one partygoer joyfully and loudly instructs her children to get a photo with Maggie to remember her by when she gets famous. Winters demurs, though the request is quickly followed by the woman quipping, “And then when you do get famous, we can sell the picture!”
Comedy clearly runs in the family.
Ryan P.C. Trimble is a freelance writer.
