Episode #492: Maggie Winters

Maggie Winters is a South Side Chicago comedian who came up in improv with iO and as a stand-up through Lincoln Lodge’s FemCom program, and she first found a wider audience online with millions of views for her front-facing character videos on TikTok and Instagram. 2023 was a breakthrough year for Winters, as she appeared as a recurring character assisting the youth group in HBO’s The Righteous Gemstones, as well as a “New Face” at Montreal’s Just For Laughs. That same year, she debuted her one-person show, Marguerite, which she took to the Edinburgh Fringe in 2024, and filmed in 2025 at the Upright Citizens Brigade Theatre in Los Angeles. The show combines onstage storytelling with video clips from her life growing up on the South Side of Chicago. Marguerite premiered on St. Patrick’s Day 2026 on the UCB’s YouTube channel, co-produced by Abso Lutely, and Winters sat down with me over Zoom to talk about her comedy start, adapting her show for people outside of Chicago, and what comes next. There’s a lot to get to, so let’s get to it!