
Stephen Colbert: A Gift from the Comedy Gods
2026/1/05 | 51 mins.
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.Please consider donating to Radio Lollipop Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Josh Johnson: Reinventing the Modern Comedy Special
2025/12/29 | 52 mins.
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 via the YouTube videos, why he thinks chasing success in the comedy industry is sometimes antithetical to the art form, and shares the advice he got from Trevor Noah. Plus, Josh helps Mike work out a new story about animals living in Mike's walls.Please consider donating to Feeding America Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

197. Natalie Palamides: Wisdom from a Modern Clown
2025/12/22 | 59 mins.
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 couple in a way that has to be seen to be believed. Mike and Natalie discuss how Natalie’s formal training in clowning informs her creative process, and they break down the philosophical differences between birthday clowns and theater clowns. Plus, Natalie explains the times that literally wresting with audience members nearly went wrong.Please consider donating to the Elysian.Get tickets for Natalie's show WEER in London here. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

196. Michael Che: An Amateur Therapy Session
2025/12/15 | 1h 12 mins.
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, how Che went from designing and selling t-shirts on the street to being a stand-up comic, and what keeps him coming back to SNL. Plus, the time Che nearly did something to Colin Jost on air that he would really regret.Please consider donating to Food Bank For NYC Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

195. Arthur Brooks: The Science of Happiness and Humor
2025/12/08 | 45 mins.
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 to Strength, and Build the Life You Want, which he co-authored with Oprah. Mike sits down with Arthur, whose speciality is the science of happiness, to explore what goes on in the brains of comedians and audiences at comedy shows. They discuss creative productivity, how Arthur prepares his lectures, and the benefits of gratitude.Please consider donating to Foundation for Excellence in Higher Education Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.



Mike Birbiglia's Working It Out