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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Bridget Everett, star of the hit HBO series “Somebody Somewhere,” joins Mike on the podcast this week to discuss creative risks and processing grief and loss through their work. Plus, that time Bridget and Patti LuPone performed together at Carnegie Hall. Also, Bridget describes the most outrageous audience reactions she has received in response to performing her songs like “Titties” and “What I Gotta Do to Get That Dick.”

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In celebration of his new album, Warriors, Lin-Manuel Miranda sits down with Mike for a wide ranging talk about writing musicals, riding the subway, and taking big creative risks. Lin explains why you need so many ideas to write a musical, and he shares the important lessons he learns from writing and performing in school plays as a student. Plus, Lin recalls the origins of Hamilton and some of the more chaotic performances in the show’s run.

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Hannah Gadsby joins Mike in the studio for the first time. The two talk Hannah’s new solo show “Woof!”, a painful celebrity encounter with Anna Kendrick, and how to keep track of multiple contradictory ideas in the creative process. Plus, a robust Working it Out session solves the mystery of if that dingo ate a baby.

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This week Mike answers listener questions. Does improv help your stand-up? What was your most nightmarish stand-up set? How do you convince yourself to keep going when it’s not going well? Plus, Mike reads a piece he wrote about his complicated but ultimately rewarding experience at the Emmys. 

11-time Grammy winner, celebrated rock star, and noted Working It Out theme song composer Jack Antonoff returns to the podcast. Mike and Jack discuss Jack’s performing with Taylor Swift and collaborating with Sabrina Carpenter, why cynicism can’t exist in a live performance, and the joys of Tim Robinson’s sketch show “I Think You Should Leave.” Plus, Mike reads excerpts from his wedding speech/roast of Jack, and a musical working it out session in which a new theme for the show is born.

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This week Matteo Lane joins Mike for an episode that has something for everyone. From Matteo’s hilariously scorching takes on modern pop stars to tales of secret families to insight about what Matteo did when he hit a wall in his comedy career. Plus, Mike and Matteo work out jokes about Mike meeting the Pope in Rome and Matteo gets serious about his Liza Minelli impression.

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Comedian Jon Laster returns for his third appearance on Working It Out. Longtime friends from the Comedy Cellar, Mike and Jon catch up on Jon’s app Blapp, which highlights black-owned businesses, Jon’s more personal comedy material about his struggles with alcoholism, and why Jon calls his company “Thanks Mom.” Plus, Mike and Jon ponder how it is that Mike, despite working in nightclubs, has never even seen cocaine.

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This week filmmaker and actor Zach Braff joins Mike to talk everything from Garden State to Ted Lasso to what it’s like to direct Morgan Freeman. Zach discusses the story of his ex once following him through Europe and Mike  and Zach discuss the possibility that a story like that could be the starting point for a one person show. Plus, the time Zach got too drunk and excused himself from a Rush concert to take New Jersey Transit home.

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Please Don't Destroy: SNL's Three Sad Virgins

(Recorded February 2024) Mike welcomes Ben Marshall, John Higgins, and Martin Herlihy, aka Please Don’t Destroy, known for their wildly popular shorts on SNL. Mike is determined to get Martin to talk more than he did on Pete Holmes’s podcast. The group shares what they like and dislike about each other, and break down what it’s like to be both sketch writers and filmmakers on SNL. Plus, what it’s like to work with Bad Bunny in a Shrek costume.

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Beloved Irish comedian Aisling Bea returns to Working It Out. Mike and Aisling discuss how to find your people, Catholic school health class, and dating app fails. Plus, new jokes about what Mike’s dad was doing while his family went to church and the most obvious and best thing about pregnancy sex.

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Click here to purchase signed print of “The Old Man & the Pool” joke cards to raise money for the YMCA New York.