Mike welcomes back the poet J. Hope Stein, aka Jenny, aka Clo, aka Mike’s wife of fifteen years. A frequent collaborator on Mike’s comedy specials and movies, Jenny describes her favorite type of creative feedback and why she’s most impressed b

The Wisdom of Chicago Improv with Liz Allen

12 days ago 46m 2s

Chicago improv performer and teacher Liz Allen taught a workshop for Mike’s college improv group almost 25 years ago. Since then, Mike and Liz have found numerous ways to reunite and collaborate, most notably on Mike’s film Don’t Think Twice. N

128. Alex Edelman Returns: He Did His Best

1 19 days ago 52m 25s

On the heels of the release of his new special “Just For Us” on Max, Alex Edelman returns to the podcast for the fourth and best time yet. Mike and Alex break apart the story of the time Alex’s bank lost all his money, how a protestor recently

127. Esther Povitsky: What Is Your Comedy Attachment Style?

26 days ago 52m 6s

Mike sits down with comedian, actor, and writer Esther Povitsky to discuss her special Hot For My Name. Mike has a lot of questions about the time Esther crashed her fiancée's bachelor party in Vegas. Plus, Esther figures out Mike’s attachment

126. Seth Meyers: SNL, Late Night, and a Ton of New Jokes

1 Mar 25th, 2024 55m 22s

Mike sits down with the legendary comedian and writer Seth Meyers for a conversation that reveals who is secretly the funniest of the funniest at SNL behind-the-scenes and who was the most popular Strike Force Five host. Then, Mike and Seth wor

125. Ilana Glazer: Life Lessons from the Broad City Star

1 Mar 18th, 2024 57m 47s

Mike became an instant super-fan of Ilana Glazer in 2014 when her hit series Broad City premiered on Comedy Central. This week on the podcast Mike and Ilana go deep on the origins of Broad City, Mike’s cameo on the show, honest takes on parenti

Mike Answers Your Questions About Comedy

1 Mar 11th, 2024 42m 15s

This week Mike responds to listener questions. How many of your stories are true? Who is your dream guest? What is your greatest piece of comedy advice? All these and more.

124. Chris Distefano: Crowd Work With The Mob

1 Mar 4th, 2024 1h 4m

This week Mike welcomes Comedy Cellar friend and comedy star Chris Distefano. Chris’s shares important lessons in failure: how a bad set got him booked on Letterman, and the advice his wife gave him about not listening to studio executives. Mik

123. Please Don't Destroy: SNL’s Three Sad Virgins

Feb 26th, 2024 1h 5m

Mike welcomes Ben Marshall, John Higgins, and Martin Herlihy, aka Please Don’t Destroy, known for their wildly popular shorts on SNL. Mike is determined to get Martin to talk more than he did on Pete Holmes’s podcast. The group shares what they

BEST OF WIO: Jim Gaffigan

Feb 19th, 2024 56m 59s

Jim Gaffigan: Dark Comedy From the Cleanest Comedian(Recorded July 2023) Mike met Jim Gaffigan in 1997 when he cold-called Jim’s New York City landline. Jim appeared as a guest on Working It Out in 2021 and now, between touring with Jerry Seinf

122. Roy Wood Jr: Perfect Jokes From an Imperfect Messenger

Feb 12th, 2024 1h 5m

Roy Wood Jr makes a triumphant return to the podcast and he and Mike pick up right where they left off. The two old friends discuss the evolution of unconnected jokes into a more cohesive whole hour of stand-up. They discuss why Mike, Neal Bren

121. Maddie Wiener: How to Find the Humor in a Panic Attack

Feb 5th, 2024 55m 24s

Maddie Wiener started performing stand-up at age 16. Now, at age 25, she headlines clubs, is a fixture at the Comedy Cellar, and she was recently a special guest on Mike’s shows at The Wilbur in Boston. Now Maddie and Mike sit down for a chat

120. Ronny Chieng Returns: Classic American Show Business

1 Jan 29th, 2024 55m 20s

Ronny Chieng, one of the earliest and most popular Working It Out guests, makes a triumphant return. Ronny and Mike discuss the significance of Ronny’s chic onstage wardrobe, the similarities between practicing law and performing comedy, and wh

BEST OF WIO: Ray Romano

Jan 22nd, 2024 51m 25s

Ray Romano: Sometimes the Setup is the Punchline(Recorded May 2023) Ray Romano has an iconic sitcom and a celebrated stand-up career under his belt, so what drives him to keep challenging himself artistically? Mike and Ray, who often follow eac

119. Rosebud Baker Returns: Pregnant with Jokes and People

Jan 15th, 2024 47m 38s

Rosebud Baker’s first appearance on Working It Out was in 2021. Since then she’s become a writer on SNL, written for That Damn Michael Che, and become a parent. Now Rosebud returns to talk with Mike about how being a parent affects comedy, and

118. John Early: A Man With Needs

1 Jan 8th, 2024 53m 3s

John Early, recently nominated for an Emmy and a Critics Choice Award, sits down with Mike for the first time since the two of them appeared as brothers in Taylor Swift’s, “Anti-Hero” music video. The two discuss avant-garde comedy, Brittany Sp

The Very Best Working It Out Moments of 2023

Jan 1st, 2024 1h 18m

We’ve created an episode for all of you making long car trips or taking long jogs or stretching out on your long beloved couch. It’s our best moments of 2023 episode! It includes Ray Romano’s take on marriage, a joke from Ramy Youssef’s funnies

Listen Now: The Sarah Silverman Podcast

Dec 27th, 2023 43m 40s

Working It Out will be back on January 1. This week, we’re sharing an episode of The Sarah Silverman Podcast, from our friends at Lemonada Media. Sarah hates men’s cologne and wants you to STOP. IT. Plus, she offers advice on setting ground ru

117. Beth Stelling Returns: Two Skeletons Telling Jokes

Dec 18th, 2023 46m 23s

Mike welcomes back to the podcast comedian Beth Stelling, whose Netflix special If You Didn’t Want Me Then is on seemingly everyone’s best of year lists, including Mike’s. Mike and Beth discuss touring together, Beth’s desire to be authentic on

116. Jimmy Carr Returns: The World Ordered A Comedian

Dec 11th, 2023 53m 17s

Jimmy Carr is one of the most successful comedians in the entire world. On the heels of playing Carnegie Hall and heading out to hundreds of concert dates across many continents, Jimmy Carr returns for another episode of Working it Out. Jimmy a

The Old Man and the Pool: Spoilers Only

Dec 4th, 2023 47m 35s

Mike welcomes back three-peat guest Joe Birbiglia to celebrate the premiere of Mike’s new Netflix comedy special The Old Man and the Pool. Mike and Joe discuss the four year development of the show, share memories about the Worcester, Massachus

115. Pete Holmes Returns (Again): The Funniest and Longest Episode Yet

Nov 27th, 2023 1h 19m

Mike’s new special, “The Old Man & The Pool” is finally on Netflix and he brings on an all-timer to celebrate. Pete Holmes returns for a third Working it Out, and he and Mike roast each other as hard as only old friends can. Mike and Pete discu

114. Jo Firestone Returns: Fact Check This Episode

1 Nov 20th, 2023 50m 17s

Jo Firestone joins Mike for her second appearance on Working it Out. In addition to just being named the head writer of the newest late night show on network TV, Jo just published a comedic murder mystery called “Murder on Sex Island” and procl

BEST OF WIO: Taylor Tomlinson

Nov 13th, 2023 52m 10s

Taylor Tomlinson Returns: She's Not Like Us(Recorded March 2022) The last time Taylor Tomlinson was on "Working it Out," she had just released her first Netflix comedy special Quarter-Life Crisis. Now, Taylor returns on the heels of her latest

113. Todd Barry: The Inventor of Crowd Work

Nov 6th, 2023 49m 5s

On the heels of the release of his new special “Domestic Shorthair,” Todd Barry sits down with Mike this week for a conversation about his 35 years in comedy. The two talk about whether or not Todd invented crowd work, if Bill Burr was right wh