165: Rachel Feinstein Returns: Everything She Says Could Be a Bit

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

(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

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

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

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

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

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

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