Advice for New-ish Comedians (with Gary Simons and Listener Questions)
Mike welcomes back comedian Gary Simons, who, since his last appearance on the podcast, opened for Mike on his latest tour, had a few of his stand-up bits go viral, and has been performing at the Come...
19 Maj 202543min
170. Please Don't Destroy Returns: The Journey of an SNL Sketch from Pitch to Air
This week PDD returns to the podcast a year and a half after originally coming on. Since then, Mike and the boys have started a monthly improv show called “Please Don’t Birbiglia” at UCB. The group ta...
12 Maj 202550min
169. Ira Glass Returns: Ira Tries Stand-Up Comedy (For Real)
Ira Glass has appeared on the Working It Out podcast three times before, and usually it’s Mike asking Ira for advice, whether it’s about podcasting or storytelling. But now the tables have turned: Ira...
5 Maj 202557min
168. Zarna Garg Returns: One Follower at a Time, a Million Times
Zarna Garg first appeared on the Working It Out podcast in 2022 and since then her popularity has continued to rise. Zarna explains to Mike how she has built her comedy career like a business, and why...
28 Apr 202552min
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
