Comedian Caleb Hearon just turned 30 and he’s already got an hour-long HBO special, hosts a hit podcast (So True with Caleb Hearon), and was named one of the top social media influencers of 2025 by Rolling Stone. But it hasn’t been an easy road. Caleb talks with Mike about his battles with suicidal ideation, how improv comedy saved his life, and how he drew on the passing of his estranged father for his comedy special. Plus, Caleb and Mike discuss the value seeing stand-up live vs. on TV, and come up with a plan to go off the grid and live in a cabin in the mountains together.Please consider donating to KC Tenants Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
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187. Jenny Slate: Unafraid of Sadness
The great Jenny Slate joins Mike this week for a wide-ranging conversation about getting hypnotized after being fired from SNL, a graduation speech Jenny gave to a class of one person, and making art to feel less lonely. Plus, jokes and stories about seeing your friends naked, improv classes for the elderly, and the time Jenny’s faked case of appendicitis went too far.Please consider donating to NPR Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
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Questlove: The Art of Self-Sabotage
Best of WIO: Questlove(Recorded April 2025) 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. Plus, what it was like accepting an Oscar after The Slap and the behind-the-scenes process of Quest’s new documentaries Sly Lives! and Ladies & Gentlemen... 50 Years of SNL Music.Please consider donating to: The Food and Finance High School Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
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186. Sebastian Maniscalco: What Is He Even Doing Here?
This week the one and only Sebastian Maniscalco sits down with Mike for a wide ranging conversation on their parenting strengths and weaknesses, the difference in what makes them cry, and Sebastian’s early days waiting on his future co-star Robert DeNiro. Plus, Sebastian reveals if he ever acts like Sebastian offstage. Please Consider Donating To: Tag, You're It! Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
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185. Julio Torres: Off-Broadway, SNL, and Why Barbie Isn’t Pink
This week Mike sits down with Julio Torres to talk comedy writing and color theories. Based on ideas posited in Julio’s new Off-Broadway solo show, Color Theories, the two of them get to the bottom of what color Barbie the Movie, Martha Stewart, and Jeremy Strong are. They also discuss the behind-the-scenes story of Julio’s viral SNL sketch, “Papyrus” starring Ryan Gosling. Plus, two encounters Julio and Mike had at the gym that aren’t sitting right with them. Please consider donating to: GLITS Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
Comedian Mike Birbiglia welcomes a different comedian or creator each week and together they work out original, untested material. And, occasionally, uncomfortable topics. Join them as they work it out.
Listen to Mike Birbiglia's Working It Out, What Did You Do Yesterday? with Max Rushden & David O'Doherty and many other podcasts from around the world with the radio.net app
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