Legendary British comedian Jimmy Carr begins his conversation with Mike by saying, “I wrote a book in lock-down because it was that or a podcast and I figured a book would be more dignified.” This begins an hour-long chat between friends that jumps from jokes to roasts to a genuine and vulnerable discussion of how laughter has the power to heal us.

https://www.smcyouthwork.org/

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Fresh off his Emmy win (with stage companion Conan O’Brien) Stephen Colbert joins Mike for a discussion of comedy, anxiety, and why he’ll never run for Senate. He explains that the reason he loves improv is that there’s nothing like failing with someone else and laughing about it with your scene partner, and he explains why Bill O’Reilly was never his scene partner.

https://somosamigos.org/

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Atsuko Okatsuka makes comedy videos featuring her grandmother & her husband, which Mike is convinced should be a feature film. The two comedians discuss Atsuko’s move from Japan at age 10, her grandmother’s run-in with a praying mantis, and why Mike might end up making a cameo in Atsuko’s feature film singing “Amazing Grace.” Earnestly.

https://downtownwomenscenter.org/

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Filmmaker Sterlin Harjo co-created the smash comedy hit Reservation Dogs for FX about four Indigenous teenagers growing up on a reservation in Oklahoma. Sterlin tells Mike about the time he accidentally taped over someone's wedding video while applying to the Sundance Film Lab. He also discusses Native representation in film & how his new series may represent some sense of hope. Many laughs. Many challenging topics. A little backstrap.

https://wellforculture.com/

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The last time Phoebe Robinson and Mike hung out, they were waiting to be picked up by an Uber on the side of a highway after their tour bus broke down. In this episode, they discuss Phoebe’s third book, "Please Don't Sit on My Bed in Your Outside Clothes,” the eternal question "to prenup or not to prenup," and why Mike was qualified to be a token white guy on Phoebe's "Sooo Many White Guys" podcast.

https://www.girlswritenow.org/

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Mike welcomes back one of our most beloved guests, Pete Holmes, to celebrate the paperback release of The New One. Pete has a lot to say about hardcovers, hardbodies, and how his father asks him questions just he so can answer them himself. Mike calls this "an expert's edition" of Working It Out because the slow round and the new material all swirl into one singular soft serve ice cream comedy cone.

https://cac.org/

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Randall Park has brought his one of a kind comedic approach to Trainwreck, Fresh Off the Boat, Veep, and the Marvel Universe. Randall reveals how he and Ali Wong scored the Keanu Reeves cameo for their film "Always Be My Maybe." Mike shares a dark version of the children’s joke “Why was 6 afraid of 7?” and Randall explains why collecting turtle figurines is indeed a skill.

https://www.kulturecity.org/

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Mike met Jim Gaffigan in 1997 when he cold-called Jim’s landline. They went out for, of course, pizza and Jim gave him advice that Mike has not only used but also shares with others. The two comics discuss the insanity of charging large pizza prices for mediums size gourmet pies, deciding not to curse on stage, and what happens when a non-political comedian has had enough. It’s Jim Gaffigan like you’ve never heard him before.

https://www.theimaginesociety.org/

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For the 50th episode Mike welcomes Kate Micucci, another member of the “Don’t Think Twice” cast. Kate is one half of the folk comedy duo Garfunkel & Oates and her creative talents stretch from music to acting to visual art. Kate shares some of her latest cartoons-in-progress and the two friends go deep on postpartum depression and its lesser known cousin “post-artum depression.“ The episode goes from silly to serious to nostalgic the way the best friendships do.

https://826national.org/

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In 2015 Mike filmed “Don’t Think Twice” where Keegan-Michael Key played a guy who got cast on a fictional version of SNL. This year Keegan hosted the *actual* SNL in a delightful case of life imitating art imitating life. Today Keegan and Mike nerd out about live sketches vs. filmed Key and Peele sketches, the wisdom of Robert Deniro, and how Keegan seems to be able to do anything, including his most recent role in the new musical comedy series Schmigadoon!

https://rfkhumanrights.org/

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