207. Chris Fleming Returns: He Is Way More Popular This Time
The last time comedian Chris Fleming was on Working it Out, the episode was titled “He Should Be Way More Popular.” In the 2 years since then Mike’s wish has come true. Chris and Mike chat about the p...
30 Mar 58min
Nathan Lane: The Safest Thing You Can Do Is Take a Risk
(Recorded February 2025) Nathan Lane sits down with Mike and recounts moments from his legendary career — discussing what it was like to work with Mike Nichols, Elaine May, and Robin Williams. He shar...
23 Mar 1h
206. Cazzie David: Spiritually a Boomer
Mike welcomes author, actor, and filmmaker Cazzie David to the podcast and right away, Mike challenges the notoriously misanthropic Cazzie to list five things she loves. It takes a while. Then, Cazzie...
16 Mar 52min
205. Taylor Tomlinson: Hope No One Filmed That
Working It Out all-timer Taylor Tomlinson returns to the podcast this week on the heels of the release of her new Netflix special, “Prodigal Daughter.” Mike and Taylor talk through what they do when t...
9 Mar 56min
204. Ali Siddiq: Telling His Own Story
Ali Siddiq is one of the most prolific storytellers in comedy. Although they work in a similar format, Ali and Mike’s paths have never crossed until now. Now they sit down to discuss the nuances of co...
2 Mar 52min
203. James Acaster: He Welcomes Hecklers
Beloved British comedian James Acaster and Mike have never met but they have a lot in common, including brushes with death early in their lives that influenced their comedy. James and Mike discuss Jam...
23 Feb 49min
Bob Odenkirk: The Art of Anger in Comedy
Best of WIO: Bob Odenkirk (Recorded July 2025)Bob Odenkirk was already a comedy legend (SNL, The Ben Stiller Show, Mr. Show with Bob and David) before he took a left turn into dramatic acting with Bre...
16 Feb 52min
202. Connor Ratliff: How and Why To Do Improv
Connor Ratliff is a beloved cult comedy figure known for his award-winning podcast Dead Eyes and his long-running live show/YouTube series The George Lucas Talk Show. He also played an improv student ...
9 Feb 56min
