115. Pete Holmes Returns (Again): The Funniest and Longest Episode Yet

115. Pete Holmes Returns (Again): The Funniest and Longest Episode Yet

Mike’s new special, “The Old Man & The Pool” is finally on Netflix and he brings on an all-timer to celebrate. Pete Holmes returns for a third Working it Out, and he and Mike roast each other as hard as only old friends can. Mike and Pete discuss Pete’s new Netflix special “I Am Not For Everyone,” the problem with Micheal Jackson’s nickname “Wacko Jacko,” and what secrets Pete has in store for his next hour of comedy. Plus, Pete literally won’t stop doing impressions: Bill Burr, Jerry Seinfeld, John Mulaney, and of course, Mike.

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Jaksot(231)

201. Heidi Gardner: Behind Your Favorite SNL Characters

201. Heidi Gardner: Behind Your Favorite SNL Characters

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 ...

3 Helmi 54min

200. John Mulaney: He’s Funny and Here’s Why

200. John Mulaney: He’s Funny and Here’s Why

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 storie...

26 Tammi 1h 12min

199. Jordan Jensen: You Can’t Say That (But Actually You Can)

199. Jordan Jensen: You Can’t Say That (But Actually You Can)

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 p...

19 Tammi 53min

198. Sarah Sherman Returns: If Chucky Went to Sarah Lawrence

198. Sarah Sherman Returns: If Chucky Went to Sarah Lawrence

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 me...

12 Tammi 52min

Stephen Colbert: A Gift from the Comedy Gods

Stephen Colbert: A Gift from the Comedy Gods

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 a...

5 Tammi 51min

Josh Johnson: Reinventing the Modern Comedy Special

Josh Johnson: Reinventing the Modern Comedy Special

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 abou...

29 Joulu 202552min

197. Natalie Palamides: Wisdom from a Modern Clown

197. Natalie Palamides: Wisdom from a Modern Clown

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 b...

22 Joulu 202559min

196. Michael Che: An Amateur Therapy Session

196. Michael Che: An Amateur Therapy Session

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...

15 Joulu 20251h 12min

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