150. Michael Ian Black: How to Do Comedy with Your 10 Best Friends

150. Michael Ian Black: How to Do Comedy with Your 10 Best Friends

In the 90s, Michael Ian Black’s college sketch group The State got a show on MTV, spawned another iconic group, Stella, and led to the classic movie Wet Hot American Summer. Now Michael sits down with Mike to talk about how all 11 members of The State have remained friends through the ups and downs of show business. Michael shares his advice on how to keep a comedy group together as well as a marriage, as he and his wife just celebrated 26 years. Plus, jokes and stories about truth or dare, the pros and cons of leaving New York City, and behind the scenes of Michael’s love scene with Bradley Cooper.

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209. Jorma Taccone Returns: This Episode Sucks

209. Jorma Taccone Returns: This Episode Sucks

Since The Lonely Island’s Jorma Taccone was last on the podcast, he survived a nearly 20 foot fall from a ladder. Now Jorma tells the full ladder story and explains how the near death experience chang...

20 Apr 50min

Nikki Glaser: The Team Captain of Comedy

Nikki Glaser: The Team Captain of Comedy

(Recorded May 2025) Nikki Glaser returns to the podcast for the first time since her acclaimed performances as the host of the Golden Globes and on the Roast of Tom Brady. Nikki breaks down her approa...

13 Apr 57min

208. Kevin Fredericks: How To Make A Comedy Show About Grief

208. Kevin Fredericks: 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 him for the first time and the two of them break o...

6 Apr 51min

207. Chris Fleming Returns: He Is Way More Popular This Time

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 Mars 58min

Nathan Lane: The Safest Thing You Can Do Is Take a Risk

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 Mars 1h

206. Cazzie David: Spiritually a Boomer

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 Mars 52min

205. Taylor Tomlinson: Hope No One Filmed That

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 Mars 56min

204. Ali Siddiq: Telling His Own Story

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 Mars 52min

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