150. Michael Ian Black: How to Do Comedy with Your 10 Best Friends

150. Michael Ian Black: How to Do Comedy with Your 10 Best Friends

In the 90s, Michael Ian Black’s college sketch group The State got a show on MTV, spawned another iconic group, Stella, and led to the classic movie Wet Hot American Summer. Now Michael sits down with Mike to talk about how all 11 members of The State have remained friends through the ups and downs of show business. Michael shares his advice on how to keep a comedy group together as well as a marriage, as he and his wife just celebrated 26 years. Plus, jokes and stories about truth or dare, the pros and cons of leaving New York City, and behind the scenes of Michael’s love scene with Bradley Cooper.

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157. Matt Rogers: Las Culturistas Meets Las Birbiglia-istas

157. Matt Rogers: Las Culturistas Meets Las Birbiglia-istas

Matt Rogers is a beloved comedian, writer, actor, and co-host of cult hit podcast “Las Culturistas.” Matt sits down with Mike for a chat about the ups and downs of show business, the inside of writing...

20 Jan 202555min

156. Stephen Colbert Returns: A Gift from the Comedy Gods

156. Stephen Colbert Returns: A Gift from the Comedy Gods

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 as his Chicago improv days. Stephen talks wisdom pass...

13 Jan 202548min

155. David Sedaris Returns: A Creative’s Dream and a Fact Checker’s Nightmare

155. David Sedaris Returns: A Creative’s Dream and a Fact Checker’s Nightmare

This week Mike has all-timer David Sedaris back on the podcast. Sedaris, of course, wrote Naked, Me Talk Pretty One Day, and Holidays on Ice, among other classics. The two discuss where the truth lies...

30 Dec 202450min

Pete Holmes and Mike Make the Definitive Christmas Movie List

Pete Holmes and Mike Make the Definitive Christmas Movie List

In this special episode of Working It Out, Mike’s old friend and frequent guest Pete Holmes sits down for a holly jolly discussion about classic and new classic Christmas movies. Mike and Pete sing th...

23 Dec 202444min

154. Fortune Feimster: Don't Borrow Trouble

154. Fortune Feimster: Don't Borrow Trouble

Hot off her new Netflix special Crushing It, Fortune Feimster sits down with Mike for a candid chat about telling personal stories on stage, dealing with audience complaints, and Fortune’s coming out ...

16 Dec 202445min

153. Maria Bamford Returns: Marketable Mania

153. Maria Bamford Returns: Marketable Mania

Mike welcomes back one of most referenced guests in Working It Out history, the legendary Maria Bamford. Mike and Maria discuss  the importance of true confession in stand-up comedy, the financials of...

2 Dec 202443min

152. Gary Gulman Returns: Mommy, Look!

152. Gary Gulman Returns: Mommy, Look!

Working It Out Hall of Famer Gary Gulman returns to discuss his upcoming Off-Broadway show Grandiloquent. Mike and Gary break down, first of all, what “grandiloquent” means, and how the new show that ...

25 Nov 202453min

151. Elizabeth Gilbert: Eat, Pray, Jokes

151. Elizabeth Gilbert: Eat, Pray, Jokes

Author Elizabeth Gilbert wrote one of Mike’s favorite books about creativity, Big Magic. She also wrote a book that, to her surprise, become a cultural phenomenon: Eat, Pray, Love. Mike and Liz discus...

18 Nov 202458min

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