Episode (200)
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167. Jessica Kirson: She's the Man
Apr 21, 2025After 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...
166. Questlove: The Art of Self-Sabotage
Apr 14, 2025This 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 nightm...
165: Rachel Feinstein Returns: Everything She Says Could Be a Bit
Apr 07, 2025Rachel Feinstein recently appeared as a surprise guest on one of Mike’s shows at the Beacon Theatre, where Mike observed after the show that everything Rachel said in the green room could be a bit. No...
164. Andrew Schulz: Give Him 10 Seconds
Mar 31, 2025This week Andrew Schulz comes on the podcast and Mike and Andrew break apart why the two of them are unlikely work friends. They discuss Andrew having Donald Trump on his podcast, Andrew’s new deeply ...
163. Josh Johnson: Reinventing the Modern Comedy Special
Mar 24, 2025Comedian Josh Johnson is a writer and correspondent for The Daily Show and his stand-up sets have millions of views on YouTube. Josh talks with Mike about cultivating a fan base via the YouTube videos...
BEST OF WIO: Mike Reads a New Piece of Writing, Plus Elizabeth Gilbert Re-Air
Mar 17, 2025At the top of this Best of WIO episode featuring Elizabeth Gilbert, Mike reads a new piece that he wrote for Elizabeth's Letters From Love Substack. (Recorded November 2024) Author Elizabeth Gilbert ...
Q&A: Mike Answers Voicemails About Comedy Advice and Crying Babies at Shows
Mar 10, 2025For this all-new Working It Out Q&A, Mike fields listener questions about people fainting at his shows, how to write comedy about topics that are painful to you, and balancing a day job and creative l...
162. Pete Holmes Returns: Comedy That’s Clean, Dirty, or PG-13
Mar 03, 2025Pete Holmes returns to help Mike punch up some last minute jokes before the premiere of Mike’s show The Good Life at the Beacon Theatre in New York. What follows is a heated debate about puns, an atte...
161. Nathan Lane Returns: The Safest Thing You Can Do Is Take a Risk
Feb 24, 2025This 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. H...
160. Rory Scovel Returns: How To Do 600 Minutes of Improvised Standup
Feb 10, 2025This 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 ...