167. Jessica Kirson: She's the Man
After 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...
21 Apr 20251h
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 nightm...
14 Apr 202558min
165: Rachel Feinstein Returns: Everything She Says Could Be a Bit
Rachel 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...
7 Apr 202553min
164. Andrew Schulz: Give Him 10 Seconds
This 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 ...
31 Mars 202545min
163. Josh Johnson: Reinventing the Modern Comedy Special
Comedian 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...
24 Mars 202552min
BEST OF WIO: Mike Reads a New Piece of Writing, Plus Elizabeth Gilbert Re-Air
At 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 wr...
17 Mars 20251h 1min
Q&A: Mike Answers Voicemails About Comedy Advice and Crying Babies at Shows
For 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...
10 Mars 202534min
162. Pete Holmes Returns: Comedy That’s Clean, Dirty, or PG-13
Pete 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...
3 Mars 202543min
