180. Kumail Nanjiani: Oh, Mary!, The Big Sick, and a Return to Stand-Up

180. Kumail Nanjiani: Oh, Mary!, The Big Sick, and a Return to Stand-Up

Kumail Nanjiani is a stand-up comedian, a movie star, and an Academy Award-nominated screenwriter. Now he’s returning to stand-up comedy after a six year break and co-starring as Abraham Lincoln in the hit Broadway show Oh, Mary!. Kumail sits down with Mike to discuss all the twists and turns of his career, including co-writing The Big Sick with his wife Emily Gordon for producer Judd Apatow. Plus, how Kumail coped with the unexpected reception of the Marvel movie Eternals, and what Elon Musk and Mark Zuckerberg really think of the show “Silicon Valley.”

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Episoder(235)

191. Todd Glass: The Ultimate Comic's Comic

191. Todd Glass: The Ultimate Comic's Comic

Todd Glass was one of the first comics Mike opened for. It’s easy to see how, since then, Todd has become one of the most beloved comic of his generation, revered by comics including Nikki Glaser, Jud...

10 Nov 202559min

190. J. Hope Stein: Eavesdropping on the Eavesdropper

190. J. Hope Stein: Eavesdropping on the Eavesdropper

This week poet J. Hope Stein & Mike’s wife ‘Clo’ returns to the podcast. Jen reads original poetry that Mike uses as inspiration for his bits—and the two dispute whose side of the story is being told ...

3 Nov 202558min

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 Okt 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 Okt 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 Okt 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 Okt 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 Sep 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 Sep 202547min

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