Chelsea Handler has achieved massive success, from her latest Netflix special The Feeling to her worldwide tours to her Las Vegas residency. But as she discusses with Mike, and details in her new book I’ll Have What She’s Having, she wasn’t always on top of the world. Chelsea tells Mike about bombing badly at Just For Laughs, and how some advice from Jane Fonda helped her during a difficult time. Plus, the story of when Chelsea unintentionally drove a giant bag of cocaine across the country, and why she felt compelled to confront Woody Allen with a very dark joke.

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This week comedy duo Jane Wickline and Liva Pierce (together known as Dukes) join Mike on the podcast. The three discuss how The Graduate brought Jane and Liva together, their unlikely porn preferences, and what happened when Jane showed up to her SNL audition early. Jane and Liva work out a couple songs from their touring show and for the first time ever on Working It Out—Mike’s jokes get set to music.

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Malik Elassal is a stand-up comic, writer, actor, and one of the stars of Adults on FX. Meeting for the first time, Mike and Malik discuss Malik’s winding road to stand-up, including working as a long haul trucker. Malik talks about dealing with his conspiracy-minded cousins, his encounters with Islamophobia, and why you should never leave your comedy set list open on your phone when you’re at the airport.

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In 2012, Mike was invited his film Sleepwalk With Me at Pixar and he’s been friends with filmmaker Pete Docter ever since. Known for his directorial feats of greatness with Monsters, Inc., Up, Soul, and Inside Out, Pete Docter is now the Chief Creative Officer at Pixar. Pete walks Mike through the Pixar “draft” process for developing a story, and reveals the ups and downs of being a Pixar director. Pete shares stories of his time spent with Steve Jobs, George Lucas, and some of the original Disney animators. Plus, advice on giving (and receiving) creative notes, and the story of Pete’s Star Wars fan film he made when he was a kid.

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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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