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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