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Music Episodes

July 6, 2025

176. Jane Wickline & Liva Pierce: SNL, Dukes, and Working Out Songs

This week comedy duo Jane Wickline and Liva Pierce (together known as Dukes) join Mike on the podcast. The three discuss how The Graduate brought Jane and Liva together, their unlikely porn preferences, and what happened when...

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June 1, 2025

Mike Reads His New York Times Essay, Plus Best of: Lin-Manuel Miranda

At the top of this Best of WIO episode featuring Lin-Manuel Miranda, Mike reads a new piece that he wrote for The New York Times . (Recorded October 2024) In celebration of his album, Warriors, Lin-Manuel Miranda sits down wi...

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April 13, 2025

166. Questlove: The Art of Self-Sabotage

This week the legendary Ahmir Thompson (aka Questlove) sits down for his first appearance on Working It Out. Mike and Questlove discuss touring with his father’s band as a kid, every DJ’s worst nightmare, and how jealousy and self-sabotage can affect even a member of a band as iconic as The Roots. …

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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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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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Jan. 7, 2024

118. John Early: A Man With Needs

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 Spears impressions, and what it means to express earnest …

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Aug. 8, 2021

50. Kate Micucci: Don't Think Thrice

For the 50th episode Mike welcomes Kate Micucci, another member of the “Don’t Think Twice” cast. Kate is one half of the folk comedy duo Garfunkel & Oates and her creative talents stretch from music to acting to visual art. Kate shares some of her latest cartoons-in-progress and the two friends go …

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Jan. 10, 2021

27. Rachel Bloom: The Inception of the “Please Stop The Ride” Musical

The award-winning co-creator and star of Crazy Ex-Girlfriend Rachel Bloom joins Mike as the two of them crack into a format never explored in this podcast—the musical! Mike leaves his prepared material behind and pitches a concept for a musical. In turn Rachel pitches Mike her first comedy special—…

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June 21, 2020

4. Matt Berninger, Carin Besser, & J. Hope Stein: The Poetry of Mike’…

Mike celebrates the publication of "The New One, Painfully True Stories from a Reluctant Dad” with his co-writer and co-wife J. Hope Stein. They are joined by Matt Berninger, the lead singer of Mike’s favorite band "The National” as well as Matt’s co-writer and co-wife Carin Besser. This creative d…

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