167. Jessica Kirson: She's the Man

167. Jessica Kirson: She's the Man

After decades of being a beloved comedian’s comedian Jessica Kirson has broken out in the last few years with viral crowd work videos and a brilliant new special on Hulu called “I’m The Man.” Mike and Jessica dig deep into the nuts and bolts and emotional work of being a stand-up comic, including overcoming stage fright and dealing with hecklers. Jessica breaks down the difference between her on stage and off stage personas, and recalls her childhood which was spent listening in, with her stepbrother Zach Braff, on her therapist mother’s sessions. Plus, Mike has an awkward experience in a steam room and Jessica tells the story of when she put a heckler up against a wall.

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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

WIO Q&A: 4th NYC Show Added and Mike Answers All of Your Questions About The Good Life

WIO Q&A: 4th NYC Show Added and Mike Answers All of Your Questions About The Good Life

In this Working It Out Q&A Mike breaks down the development of the New York City finale of his show The Good Life. He explains the evolution from Please Stop The Ride to The Good Life. Plus, he answer...

11 Nov 202426min

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...

4 Nov 202448min

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