Best of WIO: Bob Odenkirk (Recorded July 2025)

Bob Odenkirk was already a comedy legend (SNL, The Ben Stiller Show, Mr. Show with Bob and David) before he took a left turn into dramatic acting with Breaking Bad and Better Call Saul. Now he’s entered yet another new phase as an unlikely action star in films like the Nobody series. Bob sits down with Mike to discuss how anger works in comedy and action films, the stress of making Better Call Saul, and the time Bob played Mike’s brother on a TV pilot.

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Connor Ratliff is a beloved cult comedy figure known for his award-winning podcast Dead Eyes and his long-running live show/YouTube series The George Lucas Talk Show. He also played an improv student in Mike’s film Don’t Think Twice, which is a bit of a winking joke because Connor is one of the most experienced and revered improvisers on the scene. Mike and Connor go deep on improv comedy process, Connor shares some of his most devastating audition stories, and the two take a phone call from their mutual friend Chris Gethard.

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Heidi Gardner went from being a hairdresser in LA to joining the Groundlings to 8 seasons on SNL, where she created characters like “Dianne, The Mom Who's Only Read About New York on Facebook” and “A Woman Who Insists She's Not Mad.” Heidi talks with Mike about her SNL experience, which included hosting a tailgate party in her dressing room for Travis Kelce, and she shares the lessons she learned about creating comedic characters from her days in the Groundlings. Plus, Heidi’s love for her native Kansas City, and an update on Mike and Jen’s rat problem.

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For the 200th episode of Working It Out, Mike sits down with one of his oldest friends and one of the podcast’s first ever guests, John Mulaney. The two discuss monkeys wearing space suits, old stories from the road, and how John’s career changed after having kids. They work out new jokes about the time John asked Mike to go skydiving, getting yelled at by substitute teachers, and a story about an interaction with Frank Sinatra that—until Mike tells it on stage—John cannot find peace. Plus, John brings a literal buzzer into the interview so that he can hit it if he finds Mike guilty of a certain tendency.

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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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