Podcast Episodes
Back to Search208. KevOnStage: How To Make A Comedy Show About Grief
Lin-Manuel Miranda called Mike up a few months ago to say he wanted Mike to meet comedian and author Kevin Fredericks. This week, Mike sits down with…
4 months, 2 weeks ago
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 …
4 months, 3 weeks ago
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 Mi…
5 months ago
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 Mi…
5 months ago
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 fi…
5 months, 1 week ago
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…
5 months, 2 weeks ago
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 …
5 months, 3 weeks ago
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 …
6 months ago
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) befor…
6 months, 1 week ago
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…
6 months, 2 weeks ago