76. Jessi Klein: This Is the Reason For Comedy

76. Jessi Klein: This Is the Reason For Comedy

Jessi Klein is an Emmy-award winning comedian, writer, actor, and author, with a resume that includes Inside Amy Schumer, Saturday Night Live, Transparent, Kroll Show, and the voice of Jessi Glaser on Big Mouth. On top of all that, WIO listeners may remember her from Mike’s film Sleepwalk With Me where her character places a pizza pillow around Mike’s neck and then sprays him with tomato sauce. In this episode the two old friends punch up jokes and discuss why writing about being a parent can be a third rail subject. They also go deep on Jessi’s New York Times-bestselling book “I’ll Show Myself Out” and Jessi explains why the title of two of her book chapters are “In Defense of Drinking” and “Your Husband Will Remarry Five Minutes After You Die.”


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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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