Atsuko Okatsuka returns for her fourth Working It Out episode. Mike and Atsuko trace their friendship from Atsuko’s first appearance on the podcast, to opening for Mike at the Chicago Theatre, to touring with Mike across the country. Through it all Mike and Atsuko (and Atsuko’s husband and creative collaborator Ryan Harper Gray) became close friends and trusted comedy confidants. Now they discuss the delicate process of turning domestic drama into comedy, like Atsuko’s story of essentially being kidnapped by her grandmother as a child, and more recently, the time when Atsuko realized she’d never done the laundry at home, and how her husband encouraged her to make it into a bit.

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This week, Nick Kroll returns to the podcast to discuss the first season of Adults, the last season of Big Mouth and a movie that Mike cannot seem to remember the name of (I Don’t Understand You). Nick and Mike delve into the behind-the-scenes realities of Hollywood writer’s rooms, development deals, and who Nick is jealous of. Plus, the thing Nick will always regret saying to Robert DeNiro.

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At the top of this Best of WIO episode featuring Lin-Manuel Miranda, Mike reads a new piece that he wrote for The New York Times.

(Recorded October 2024) In celebration of his 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.

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Nikki Glaser returns to the podcast for the first time since her acclaimed performances as the host of the Golden Globes and on the Roast of Tom Brady. Nikki breaks down her approach to the Golden Globes, explains her perspective on controversial comedy topics, and explores the possibility of a “vegan hour” of comedy. Plus, Nikki’s awkward encounter with Lana Del Ray, and Mike’s new special The Good Life arrives on Netflix!

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Mike welcomes back comedian Gary Simons, who, since his last appearance on the podcast, opened for Mike on his latest tour, had a few of his stand-up bits go viral, and has been performing at the Comedy Cellar. Now, Mike and Gary answer listener questions from people who have taken the leap into stand-up comedy and are looking for advice about how to continue. They discuss open mics, bombing, pre-show mantras, and more.

This week PDD returns to the podcast a year and a half after originally coming on. Since then, Mike and the boys have started a monthly improv show called “Please Don’t Birbiglia” at UCB. The group talks about what it’s like to improvise together, the unsparing roasts PDD did of Mike when they opened for his show "The Good Life," and the creation of PDD’s Jon Hamm pizza sketch—from Monday’s pitch in Lorne’s office to airing live on SNL. Plus, the unlikely thing that shows up in more than one PDD member’s Instagram algorithm.

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Ira Glass has appeared on the Working It Out podcast three times before, and usually it’s Mike asking Ira for advice, whether it’s about podcasting or storytelling. But now the tables have turned: Ira recently listened to a stand-up set he performed years ago, he has the itch to try it again, so he’s come to Mike for comedy advice. On this episode, Mike and Ira listen to Ira’s old stand-up set in real time, break down what worked and what didn’t, and brainstorm ideas for Ira’s next set.

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Zarna Garg first appeared on the Working It Out podcast in 2022 and since then her popularity has continued to rise. Zarna explains to Mike how she has built her comedy career like a business, and why performing for an audience of one or two is no different for her than performing for an audience of thousands. Mike and Zarna discuss free speech in Zarna’s native India, and what it’s like for her to raise her kids in America. Plus: why no one in Zarna’s family has been allowed to read her memoir This American Woman.

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