Episode (200)
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199. Jordan Jensen: You Can’t Say That (But Actually You Can)
Jan 19, 2026This week Mike sits down with comedian Jordan Jensen. A master of turning taboo topics into comedy- as seen in her Netflix special Take Me With You- Jordan explains how her fearless, no filter stage p...
198. Sarah Sherman Returns: If Chucky Went to Sarah Lawrence
Jan 12, 2026This week, SNL’s Sarah Sherman returns on the heels of the release of her new HBO special, “Live + In the Flesh.” Sarah and Mike discuss why Sarah goes to therapy three times a week, which SNL cast me...
Stephen Colbert: A Gift from the Comedy Gods
Jan 05, 2026Best 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...
Josh Johnson: Reinventing the Modern Comedy Special
Dec 29, 2025Best 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 ab...
197. Natalie Palamides: Wisdom from a Modern Clown
Dec 22, 2025Natalie 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 b...
196. Michael Che: An Amateur Therapy Session
Dec 15, 2025Mike 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...
195. Arthur Brooks: The Science of Happiness and Humor
Dec 08, 2025Arthur 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 Happin...
194. Pete Holmes Returns: Vulnerability is Everything
Dec 01, 2025This 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...
193. Vir Das Returns: How to Find Your Voice, Literally
Nov 24, 2025The last time comedian Vir Das was on Working It Out, he and Mike discussed the intense reaction to a piece he performed called “Two Indias.” Now Vir returns to share how he moved on from the controve...
192. Leanne Morgan: In The Presence of a Comedy Angel
Nov 17, 2025On the heels of her new special “Unspeakable Things,” Leanne Morgan joins the podcast this week to talk Southern beauty shop gossip, getting started in comedy selling jewelry door to door, and in what...