204. Ali Siddiq: Telling His Own Story

Best of WIO: Stephen Colbert (Recorded January 2025)This week the legendary Stephen Colbert returns to the podcast. Mike and Stephen discuss the behind-the-scenes of Stephen’s Late Night job as well a...

5 Jan 51min

Best of WIO: Josh Johsnon(Recorded March 2025) Comedian Josh Johnson is a writer and correspondent for The Daily Show and his stand-up sets have millions of views on YouTube. Josh talks with Mike abou...

29 Dec 202552min

Natalie Palamides is a writer and performer best known for her avant-garde comedy shows Laid, Nate, and WEER. She’s eaten raw eggs on stage, fondled audience members (with their consent), and played b...

22 Dec 202559min

Mike started this podcast so that one day Michael Che would come on. Today is that day. In this all-timer episode, Mike and Che work out tons of jokes and discuss the advice Lorne Michaels gave to Che...

15 Dec 20251h 12min

Arthur Brooks might be the only Working It Out guest who's crossed paths with Jerry Seinfeld, Oprah Winfrey, and the Dalai Lama. He’s a professor and bestselling author, whose books include The Happin...

8 Dec 202545min

This week, Pete Holmes returns to the studio for one of Working It Out’s most joke-dense episodes ever. Mike and Pete work out jokes about strangers in hot tubs, why Jerry Seinfeld sounds like his own...

1 Dec 20251h 3min

The last time comedian Vir Das was on Working It Out, he and Mike discussed the intense reaction to a piece he performed called “Two Indias.” Now Vir returns to share how he moved on from the controve...

24 Nov 202554min

On the heels of her new special “Unspeakable Things,” Leanne Morgan joins the podcast this week to talk Southern beauty shop gossip, getting started in comedy selling jewelry door to door, and in what...

17 Nov 202542min