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!

Mark Vigeant blends clown, improv, physical theater, and multimedia to create interactive comedy shows such as The Best Man Show, which he took to the Edinburgh Fringe in 2024 and 2025, and released as a special on Dropout in February 2026. Vigeant is based in Los Angeles, but started his career with the Upright Citizens Brigade in New York City where he performed improv and sketch, played Trumpet Boy for The Special Without Brett Davis, hosted a series online for Seriously.TV, and earned himself a screen-test audition for Saturday Night Live. Vigeant caught up with me over Zoom to talk about how his brushes with near-stardom, as well as his 2021 documentary about the "Pizza Rat" phenomenon, influenced his views on fame and ambition; how he was inspired by seeing other Fringe shows by the likes of Moses Storm, Natalie Palamides and The Umbilical Brothers, and how releasing a Dropout special has influenced what he's doing next: a 2026 Fringe show about a YouTube survivalist called Out There. There's a lot to get to, so let's get to it!

Jamie Lee is an Emmy-winning writer and producer on Apple TV's Ted Lasso who began her comedy career in the press office of Comedy Central. Her first break in front of the camera came via panel shows, most notably MTV's Girl Code, as well as performances on both Conan and The Late Late Show with James Corden. As a writer, her credits have included HBO's Crashing, TV Land's Teachers, Peocock's Killing It, Hulu's Chad Powers, and of course, Ted Lasso. Her book Weddiculous, led to her starring in the Netflix series, The Wedding Coach. But her current passion project is a stage show, My Friend Katy, investigating how and why her childhood friend died suddenly and mysteriously while Lee was in college. Lee took the show to the Edinburgh Fringe in 2025, and she caught up with me over Zoom in March 2026 between shows at Union Hall in Brooklyn as she prepares to adapt her stage show into a special. There's a lot to get to, so let's get to it!