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Episodes

Feb. 23, 2025

161. Nathan Lane Returns: The Safest Thing You Can Do Is Take a Risk

This week, the great Nathan Lane returns to Working it Out. Nathan recounts moments from his legendary career — discussing what it was like to work with Mike Nichols, Elaine May, and Robin Williams. He shares what he likes most in a director, who he’s jealous of, and what he remembers of twenty-som…

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Feb. 9, 2025

160. Rory Scovel Returns: How To Do 600 Minutes of Improvised Standup

This week Rory Scovel returns to the podcast with his review of how doing a year of completely improvised stand-up went. Mike and Rory dive into the creative process and their own fears on stage, why Rory is jealous of other comedians, and why someone being married to a comedian is hard because eve…

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Feb. 2, 2025

159. Hasan Minhaj Returns: Off with His Head, On with His Jokes

Working It Out fan favorite Hasan Minhaj returns for a third episode. Mike and Hasan discuss the enduring memories of childhood crushes, an obsession with who was the fastest in elementary school, and why comedy and politics move in cycles. Plus, Hasan keeps Google Image searching Mike, and Mike in…

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Jan. 26, 2025

158. Ben Stiller and Adam Scott: Working it Innie and Outie

This week Mike sits down with Severance’s very own Ben Stiller and Adam Scott. The three of them dig into the behind the scenes of Severance Season 2 and discuss what it is that makes them work so well together as actor and director. Ben and Adam share audition advice for actors, as well as how th…

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Jan. 19, 2025

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 for a hit TV series, and what it was like when Matt and his podcast co-host Bowen Yang were both i…

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Jan. 12, 2025

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 passed down to him by David Letterman, Del Close, and Mike Nichols, and shares what makes him cry most …

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Dec. 29, 2024

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

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 in autobiographical non-fiction, fact-checking comedy at The New Yorker, and how to navigate story…

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Dec. 22, 2024

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 the praises of Elf, examine the dark underbelly of A Christmas Story, and take Gremlins to task over …

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Dec. 15, 2024

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 journey. Fortune also explains her dynamic with her Handsome podcast co-hosts Tig Notaro and Mae Ma…

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Dec. 1, 2024

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 being a comedian, and why Maria works out new material one on one with strangers on coffee shops. …

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Nov. 24, 2024

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 looks back on Gary’s early life and looks ahead at the prospect of Gary becoming a father. Mike and…

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Nov. 17, 2024

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 discuss the unexpected impact of Eat, Pray, Love, and what it was like for Liz to watch Julia Roberts por…

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Nov. 10, 2024

WIO Q&A: 4th NYC Show Added and Mike Answers All of Your Questions Ab…

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 answers your questions about embarrassment, fear, jealousy, and inspiration.

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Nov. 3, 2024

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…

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Oct. 27, 2024

149. Bridget Everett: The Star of HBO’s Somebody Somewhere on Risking…

Bridget Everett, star of the hit HBO series “Somebody Somewhere,” joins Mike on the podcast this week to discuss creative risks and processing grief and loss through their work. Plus, that time Bridget and Patti LuPone performed together at Carnegie Hall. Also, Bridget describes the most outrageous…

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Oct. 20, 2024

148. Lin-Manuel Miranda: Everything is Basically the School Play

In celebration of his new album, Warriors, Lin-Manuel Miranda sits down with Mike for a wide ranging talk about writing musicals, riding the subway, and taking big creative risks. Lin explains why you need so many ideas to write a musical, and he shares the important lessons he learns from writing …

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Oct. 13, 2024

147. Hannah Gadsby Returns: Shake the Tree

Hannah Gadsby joins Mike in the studio for the first time. The two talk Hannah’s new solo show “Woof!”, a painful celebrity encounter with Anna Kendrick, and how to keep track of multiple contradictory ideas in the creative process. Plus, a robust Working it Out session solves the mystery of if tha…

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Oct. 6, 2024

Mike Answers Your Questions About Creativity and Discusses The Emmys

This week Mike answers listener questions. Does improv help your stand-up? What was your most nightmarish stand-up set? How do you convince yourself to keep going when it’s not going well? Plus, Mike reads a piece he wrote about his complicated but ultimately rewarding experience at the Emmys.

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Sept. 29, 2024

146. Jack Antonoff Returns: Working Out the New Theme Song

11-time Grammy winner, celebrated rock star, and noted Working It Out theme song composer Jack Antonoff returns to the podcast. Mike and Jack discuss Jack’s performing with Taylor Swift and collaborating with Sabrina Carpenter, why cynicism can’t exist in a live performance, and the joys of Tim Rob…

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Sept. 22, 2024

145. Matteo Lane: Working Towards the Masterpiece

This week Matteo Lane joins Mike for an episode that has something for everyone. From Matteo’s hilariously scorching takes on modern pop stars to tales of secret families to insight about what Matteo did when he hit a wall in his comedy career. Plus, Mike and Matteo work out jokes about Mike meetin…

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Sept. 15, 2024

144. Jon Laster Returns: The Throughline Is Habits

Comedian Jon Laster returns for his third appearance on Working It Out. Longtime friends from the Comedy Cellar, Mike and Jon catch up on Jon’s app Blapp, which highlights black-owned businesses, Jon’s more personal comedy material about his struggles with alcoholism, and why Jon calls his company …

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Sept. 8, 2024

143. Zach Braff: Making A Movie is Like Throwing A Wedding

This week filmmaker and actor Zach Braff joins Mike to talk everything from Garden State to Ted Lasso to what it’s like to direct Morgan Freeman. Zach discusses the story of his ex once following him through Europe and Mike  and Zach discuss the possibility that a story like that could be the start…

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Aug. 25, 2024

142. Aisling Bea Returns: We Like You Here

Beloved Irish comedian Aisling Bea returns to Working It Out. Mike and Aisling discuss how to find your people, Catholic school health class, and dating app fails. Plus, new jokes about what Mike’s dad was doing while his family went to church and the most obvious and best thing about pregnancy sex.

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Aug. 18, 2024

141. Hannah Berner: Zaddy Issues

Mike welcomes fellow comedian and podcaster (Giggly Sqaud, Berner Phone) Hannah Berner to the pod. Known for her “Han on the Street” videos, Hannah discusses her journey from college tennis champ to stand-up sensation. Hannah also teaches Mike the meaning of the term “zaddy.” Plus, an athlete at he…

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