170. Please Don't Destroy Returns: The Journey of an SNL Sketch from Pitch to Air

170. Please Don't Destroy Returns: The Journey of an SNL Sketch from Pitch to Air

This week PDD returns to the podcast a year and a half after originally coming on. Since then, Mike and the boys have started a monthly improv show called “Please Don’t Birbiglia” at UCB. The group talks about what it’s like to improvise together, the unsparing roasts PDD did of Mike when they opened for his show "The Good Life," and the creation of PDD’s Jon Hamm pizza sketch—from Monday’s pitch in Lorne’s office to airing live on SNL. Plus, the unlikely thing that shows up in more than one PDD member’s Instagram algorithm.

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Episoder(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 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

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 Des 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 Des 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 Des 20251h 12min

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