190. J. Hope Stein: Eavesdropping on the Eavesdropper

190. J. Hope Stein: Eavesdropping on the Eavesdropper

This week poet J. Hope Stein & Mike’s wife ‘Clo’ returns to the podcast. Jen reads original poetry that Mike uses as inspiration for his bits—and the two dispute whose side of the story is being told in each. Mike and Jen discuss helpful vs. unhelpful artistic feedback, the difference between Mike in real life and Mike on the podcast, and Mike has Jen participate in The Introverted Slow Round. Plus, a phone call from Pete Homes and his wife Val!

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203. James Acaster: He Welcomes Hecklers

203. James Acaster: He Welcomes Hecklers

Beloved British comedian James Acaster and Mike have never met but they have a lot in common, including brushes with death early in their lives that influenced their comedy. James and Mike discuss Jam...

23 Feb 49min

Bob Odenkirk: The Art of Anger in Comedy

Bob Odenkirk: The Art of Anger in Comedy

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 Bre...

16 Feb 52min

202. Connor Ratliff: How and Why To Do Improv

202. Connor Ratliff: How and Why To Do Improv

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 ...

9 Feb 56min

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 Feb 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 Jan 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 Jan 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 Jan 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 Jan 51min

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