This 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 persona coexists with her emotional, more vulnerable side. Plus, the story of how caring for her paralyzed friend led her to stand-up, why Jordan almost bit Laura Dern on the set of Bradley Cooper’s film Is This Thing On?, and the time someone from the audience tried to fight her.

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This 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 member Sarah is jealous of, and the difference between Sarah Sherman and her stage persona Sarah Squirm. Plus, the Weekend Update character that Lorne Michaels himself thought of for Sarah to play.

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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.

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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.

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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.

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Get tickets for Natalie's show WEER in London here.

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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.

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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.

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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 in movies swallow their pills without water. Plus, the comedy advice Pete wishes he knew when he was starting out.

Want more of Mike and Pete? Subscribe to Working It Out’s premium feed on Apple Podcasts to listen to their bonus episode together where they work out listener-submitted material! 

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The 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 controversy, and all the ups and downs he’s experienced since then, including: literally losing his voice just weeks before sold out shows in Mumbai, writing a memoir, and making an independent film. Plus, Mike and Vir dive into the two different shows Vir is currently performing, and Vir explains why Mike’s name belongs in a Bollywood musical.

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On 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 way Mike is “her Elvis.” Plus, the time Leanne may or may not have been picked up in an SUV by President George W. Bush.

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