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
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
