Episodes

  • 151. Elizabeth Gilbert: Eat, Pray, Jokes
    Nov 18 2024

    Author Elizabeth Gilbert wrote one of Mike’s favorite books about creativity, Big Magic. She also wrote a book that, to her surprise, become a cultural phenomenon: Eat, Pray, Love. Mike and Liz discuss the unexpected impact of Eat, Pray, Love, and what it was like for Liz to watch Julia Roberts portray her on the big screen. Liz gets candid about the ups and downs of a creative life, including the reasoning behind the cancellation of a novel she wrote that took place in Russia. Plus, some bawdy jokes and stories care of Liz’s uncles and grandfather, and the surprising reason why Liz was stopped at airport security.

    Please consider donating to The Loveland Foundation

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    59 mins
  • WIO Q&A: 4th NYC Show Added and Mike Answers All of Your Questions About The Good Life
    Nov 11 2024

    In this Working It Out Q&A Mike breaks down the development of the New York City finale of his show The Good Life. He explains the evolution from Please Stop The Ride to The Good Life. Plus, he answers your questions about embarrassment, fear, jealousy, and inspiration.

    Get tickets to The Good Life at the Beacon Theatre

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    27 mins
  • 150. Michael Ian Black: How to Do Comedy with Your 10 Best Friends
    Nov 4 2024

    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.

    Please consider donating to the Mark Twain Library.

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    48 mins
  • 149. Bridget Everett: The Star of HBO’s Somebody Somewhere on Risking It All
    Oct 28 2024

    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.”

    Please consider donating to True Colors Flint Hills.

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    49 mins
  • 148. Lin-Manuel Miranda: Everything is Basically the School Play
    Oct 21 2024

    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.

    Please consider donating to RISE Theatre.

    Get tickets for Mike’s shows at the Beacon Theatre in New York here.

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    56 mins
  • 147. Hannah Gadsby Returns: Shake the Tree
    Oct 14 2024

    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.

    Please consider donating to: The Autistic Self Advocacy Network

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    58 mins
  • Mike Answers Your Questions About Creativity and Discusses The Emmys
    Oct 7 2024

    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.

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    41 mins
  • 146. Jack Antonoff Returns: Working Out the New Theme Song
    Sep 30 2024

    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.

    Please consider donating to The Ally Coalition

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    54 mins