166. Questlove: The Art of Self-Sabotage

166. Questlove: The Art of Self-Sabotage

This week the legendary Ahmir Thompson (aka Questlove) sits down for his first appearance on Working It Out. Mike and Questlove discuss touring with his father’s band as a kid, every DJ’s worst nightmare, and how jealousy and self-sabotage can affect even a member of a band as iconic as The Roots. Plus, what it was like accepting an Oscar after The Slap and the behind-the-scenes process of Quest’s new documentaries Sly Lives! and Ladies & Gentlemen... 50 Years of SNL Music.

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Jaksot(233)

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 Helmi 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 Helmi 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 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

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