122. Roy Wood Jr: Perfect Jokes From an Imperfect Messenger

122. Roy Wood Jr: Perfect Jokes From an Imperfect Messenger

Roy Wood Jr makes a triumphant return to the podcast and he and Mike pick up right where they left off. The two old friends discuss the evolution of unconnected jokes into a more cohesive whole hour of stand-up. They discuss why Mike, Neal Brennan, and Chris Rock are all pressuring Roy to go even deeper with his new material about his dad. Mike and Roy break down the best bits from Roy’s new special Imperfect Messenger, and Roy shares two all-timer stories in the slow round. Plus, Roy gets candid on exactly why he may or may not be hosting The Daily Show.

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Jaksot(233)

189. Nick Offerman: The Man Behind the Mustache

189. Nick Offerman: The Man Behind the Mustache

Mike met Nick Offerman years ago at the Sasquatch! Music Festival in Washington state, which is fitting because Nick is a man of nature, almost as well known for his woodworking as he is for his actin...

27 Loka 202557min

Caleb Hearon: Improv Saved His Life

Caleb Hearon: Improv Saved His Life

Comedian Caleb Hearon just turned 30 and he’s already got an hour-long HBO special, hosts a hit podcast (So True with Caleb Hearon), and  was named one of the top social media influencers of 2025 by R...

20 Loka 20251h

187. Jenny Slate: Unafraid of Sadness

187. Jenny Slate: Unafraid of Sadness

The great Jenny Slate joins Mike this week for a wide-ranging conversation about getting hypnotized after being fired from SNL, a graduation speech Jenny gave to a class of one person, and making art ...

13 Loka 20251h 10min

Questlove: The Art of Self-Sabotage

Questlove: The Art of Self-Sabotage

Best of WIO: Questlove(Recorded April 2025) The legendary Ahmir Thompson (aka Questlove) sits down for his first appearance on Working It Out. Mike and Questlove discuss touring with his father’s band...

6 Loka 202557min

186. Sebastian Maniscalco: What Is He Even Doing Here?

186. Sebastian Maniscalco: What Is He Even Doing Here?

This week the one and only Sebastian Maniscalco sits down with Mike for a wide ranging conversation on their parenting strengths and weaknesses, the difference in what makes them cry, and Sebastian’s ...

29 Syys 202553min

185. Julio Torres: Off-Broadway, SNL, and Why Barbie Isn’t Pink

185. Julio Torres: Off-Broadway, SNL, and Why Barbie Isn’t Pink

This week Mike sits down with Julio Torres to talk comedy writing and color theories. Based on ideas posited in Julio’s new Off-Broadway solo show, Color Theories, the two of them get to the bottom of...

22 Syys 202547min

Announcing Working It Out Premium

Announcing Working It Out Premium

Mike announces Working It Out Premium Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

17 Syys 202557s

184. KC Shornima: Get Comfortable With This Darkness

184. KC Shornima: Get Comfortable With This Darkness

Comedian and SNL writer KC Shornima might be the only Working It Out guest who has climbed Mount Kilimanjaro. KC and Mike get to the bottom of why she thrives in stressful situations like mountain cli...

15 Syys 20251h 4min

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