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Mike Birbiglia Working It Out Feat. Caleb Hearon [Podcast]

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Comedian Mike Birbiglia welcomes a different comedian or creator each week and together they work out original, untested material. And, occasionally, uncomfortable topics. Join them as they work it out.

Mike Birbiglia: A comedian, storyteller, director and actor who has performed in front of audiences worldwide, from the Sydney Opera House to Broadway. His shows, “My Girlfriend’s Boyfriend” and “Thank God for Jokes,” were both filmed for Netflix. His most recent show, “The New One,” ran for 99 shows at the Cort Theatre.

In addition to performing live, Mike is an author and filmmaker who wrote, directed and starred in the films Sleepwalk with Me and Don’t Think Twice. Mike’s book “Sleepwalk with Me and Other Painfully True Stories” was a New York Times bestseller and a finalist for the Thurber Prize for American Humor. As an actor, Mike has appeared on “Inside Amy Schumer,” HBO’s “Girls” and “Broad City,” as well as in the films Trainwreck, The Fault in Our Stars and Popstar. He plays the role of Danny Pearson on “Orange Is the New Black” and Oscar Langstraat on Showtime’s “Billions.” He is a contributor to “This American Life” on public radio. In 2017, Mike was honored with the Kurt Vonnegut Award for humor. 

In this week’s episode, 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 Rolling Stone.

But it hasn’t been an easy road. Caleb talks with Mike about his battles with suicidal ideation, how improv comedy saved his life, and how he drew on the passing of his estranged father for his comedy special.

Plus, Caleb and Mike discuss the value seeing stand-up live vs. on TV, and come up with a plan to go off the grid and live in a cabin in the mountains together.

Checkout previous episodes featuring Nikki Glaser, Seth Meyers, & more HERE