Best of WIO: Stephen Colbert (Recorded January 2025) This week the legendary Stephen Colbert returns to the podcast. Mike and Stephen discuss the behind-the-scenes of Stephen’s Late Night job as well as his Chicago improv days. Stephen talks wisdom passed down to him by David Letterman, Del Close, and Mike Nichols, and shares what makes him cry most easily. Plus, Stephen’s thoughts on meeting George Lucas and the Pope.
Best of WIO: Stephen Colbert (Recorded January 2025) This week the legendary Stephen Colbert returns to the podcast. Mike and Stephen discuss the behind-the-scenes of Stephen’s Late Night job as well as his Chicago improv days. Stephen talks wisdom passed down to him by David Letterman, Del Close, …
Best of WIO: Josh Johsnon (Recorded March 2025) Comedian Josh Johnson is a writer and correspondent for The Daily Show and his stand-up sets have millions of views on YouTube. Josh talks with Mike about cultivating a fan base...
Natalie Palamides is a writer and performer best known for her avant-garde comedy shows Laid, Nate, and WEER. She’s eaten raw eggs on stage, fondled audience members (with their consent), and played both halves of a feuding c...
Mike started this podcast so that one day Michael Che would come on. Today is that day. In this all-timer episode, Mike and Che work out tons of jokes and discuss the advice Lorne Michaels gave to Che that he’ll never forget,...
Arthur Brooks might be the only Working It Out guest who's crossed paths with Jerry Seinfeld, Oprah Winfrey, and the Dalai Lama. He’s a professor and bestselling author, whose books include The Happiness Files, From Strength ...
This week, Pete Holmes returns to the studio for one of Working It Out’s most joke-dense episodes ever. Mike and Pete work out jokes about strangers in hot tubs, why Jerry Seinfeld sounds like his own name, and how cool guys ...
Mike Birbiglia is an Emmy-nominated comedian, writer, director, and actor who has performed his award-winning solo shows worldwide—from the Sydney Opera House to the West End of London to Broadway. His six solo shows Sleepwalk With Me, My Girlfriend’s Boyfriend, Thank God For Jokes, The New One, The Old Man & The Pool, and The Good Life enjoyed successful runs on and off Broadway and became hit Netflix comedy specials. The shows merge storytelling and comedy in a way that The New York Times has called “Birbiglian.” Birbiglia also wrote, directed, and starred in the films Sleepwalk with Me and Don’t Think Twice. As an actor, Birbiglia has appeared in the films Trainwreck, The Fault in Our Stars, Popstar, and A Man Called Otto, as well as TV roles in Orange Is the New Black and Billions. He hosts the podcast Mike Birbiglia's Working It Out.