At the top of this Best of WIO episode featuring Elizabeth Gilbert, Mike reads a new piece that he wrote for Elizabeth's Letters From Love Substack.

(Recorded November 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. 

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For this all-new Working It Out Q&A, Mike fields listener questions about people fainting at his shows, how to write comedy about topics that are painful to you, and balancing a day job and creative life when starting out. If your question didn’t get answered on this week’s Q&A, stay tuned for another one soon where Mike answers the rest! Got a new question? Email [email protected] with a VoiceMemo asking your question.

Pete Holmes returns to help Mike punch up some last minute jokes before the premiere of Mike’s show The Good Life at the Beacon Theatre in New York. What follows is a heated debate about puns, an attempt to define and dissect the nature of “clean” comedy, and, yes, a nuts and bolts joke writing session. Plus, Pete psychoanalyzes the state of Massachusetts, and Mike recalls the time he opened for Tracy Morgan.

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This week, the great Nathan Lane returns to Working it Out. Nathan recounts moments from his legendary career — discussing what it was like to work with Mike Nichols, Elaine May, and Robin Williams. He shares what he likes most in a director, who he’s jealous of, and what he remembers of twenty-something year old Mike. Plus, an incredible story about working with Joaquin Phoenix on the film Beau is Afraid. Nathan’s new highly-anticipated series, Mid-Century Modern, drops March 28 on Hulu.

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Tig Notaro: Clown Cars and Lesbian Party Buses

(Recorded July 2024) Mike welcomes back old friend and Working It Out hall of famer Tig Notaro. They discuss the inevitability of finding your own comedic voice, how Tig had to come out as gay to her own children, and the time her brother fell into her stepfather’s grave. All that, plus tales from Tig’s lesbian party bus with Sarah Paulson and Allison Janney.

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This week Rory Scovel returns to the podcast with his review of how doing a year of completely improvised stand-up went. Mike and Rory dive into the creative process and their own fears on stage, why Rory is jealous of other comedians, and why someone being married to a comedian is hard because every day that comedian  has a “presentation at work.” Plus, the two comics work out new jokes about brain bleeds and how to figure out where your daughter goes to school. 

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Working It Out fan favorite Hasan Minhaj returns for a third episode. Mike and Hasan discuss the enduring memories of childhood crushes, an obsession with who was the fastest in elementary school, and why comedy and politics move in cycles. Plus, Hasan keeps Google Image searching Mike, and Mike invites himself along on a hangout with Hasan’s high school friend group The Hit Squad.

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This week Mike sits down with Severance’s very own Ben Stiller and Adam Scott. The three of them dig into the behind the scenes of Severance Season 2 and discuss what it is that makes them work so well together as actor and director.  Ben and Adam share audition advice for actors, as well as how their grieving processes influenced their work together. Plus, Mike and Adam nerd out about The Ben Stiller Show and Reality Bites, and Mike reveals which Severance character he almost played.

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Matt Rogers is a beloved comedian, writer, actor, and co-host of cult hit podcast “Las Culturistas.” Matt sits down with Mike for a chat about the ups and downs of show business, the inside of writing for a hit TV series, and what it was like when Matt and his podcast co-host Bowen Yang were both invited to audition for SNL. Matt also discusses why having fun is the most important ingredient for creativity. Plus, advice via Jessica Chastain and why Mike somewhat regularly has to throw muffins in the garbage.

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This week the legendary Stephen Colbert returns to the podcast. Mike and Stephen discuss the behind-the-scenes of Stephen’s Late Night job as well as his Chicago improv days. Stephen talks wisdom passed down to him by David Letterman, Del Close, and Mike Nichols, and shares what makes him cry most easily. Plus, Stephen’s thoughts on meeting George Lucas and the Pope.

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