Jo Firestone is a multi-talented writer, actor, and comedian. In her third appearance on Working It Out, Jo explains the thought process behind her experimental live comedy shows, which often involve clay, paper mache, and pie. Jo also delves into the experience of working as the head writer for After Midnight with Taylor Tomlinson and discusses being the subject of a search warrant by the Paramount lot police after a golf cart mishap. Plus, Jo and Mike break down the various text acronyms for laughter and compare their experiences taking martial arts classes.

Kumail Nanjiani is a stand-up comedian, a movie star, and an Academy Award-nominated screenwriter. Now he’s returning to stand-up comedy after a six year break and co-starring as Abraham Lincoln in the hit Broadway show Oh, Mary!. Kumail sits down with Mike to discuss all the twists and turns of his career, including co-writing The Big Sick with his wife Emily Gordon for producer Judd Apatow. Plus, how Kumail coped with the unexpected reception of the Marvel movie Eternals, and what Elon Musk and Mark Zuckerberg really think of the show “Silicon Valley.”

For this all-new Working It Out Q&A, Mike fields listener questions about how and why he cuts jokes that he loves, the impact AI might have on comedy, and how to navigate weird or bad energy from an audience. Plus, how to get motived for creative work, and how to restart stand-up comedy after a long pause. Got a question for Mike? Send a voicemail at birbigs.com/wio.

Bob Odenkirk was already a comedy legend (SNL, The Ben Stiller Show, Mr. Show with Bob and David) before he took a left turn into dramatic acting with Breaking Bad and Better Call Saul. Now he’s entered yet another new phase as an unlikely action star in films like the Nobody series. Bob sits down with Mike to discuss how anger works in comedy and action films, the stress of making Better Call Saul, and the time Bob played Mike’s brother on a TV pilot.

With his fifth appearance, comedian Alex Edelman is the most frequent guest on Working It Out. Since his last appearance, Alex won an Emmy for his HBO stand-up special Just For Us, which Mike was a producer on. Now Alex is back on the road with a new hour of comedy, including a just-announced visit to Carnegie Hall. Alex discusses Boston sports memories, whether AI will replace comedians, and grieving the death of his creative collaborator Adam Brace. Plus, Alex’s rocky stint as a hospital clown, and his new job as a writer and actor on Greg Daniels’ highly anticipated follow up to The Office: The Paper.

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.

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.

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. Please Consider Donating To: The Red Cross

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.

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.

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. Please consider donating to: Memorial Sloan Kettering Cancer Center

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.

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!

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. Please consider donating to: https://www.housingworks.org/

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. Please consider donating to your local public radio or television station.

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.

After decades of being a beloved comedian’s comedian Jessica Kirson has broken out in the last few years with viral crowd work videos and a brilliant new special on Hulu called “I’m The Man.” Mike and Jessica dig deep into the nuts and bolts and emotional work of being a stand-up comic, including overcoming stage fright and dealing with hecklers. Jessica breaks down the difference between her on stage and off stage personas, and recalls her childhood which was spent listening in, with her stepbrother Zach Braff, on her therapist mother’s sessions. Plus, Mike has an awkward experience in a steam room and Jessica tells the story of when she put a heckler up against a wall.

This week the legendary Ahmir Thompson (aka Questlove) sits down for his first appearance on Working It Out. Mike and Questlove discuss touring with his father’s band as a kid, every DJ’s worst nightmare, and how jealousy and self-sabotage can affect even a member of a band as iconic as the Roots. Plus, what it was like accepting an Oscar after The Slap and the behind-the-scenes process of Quest’s new documentary Sly Lives!

Rachel Feinstein recently appeared as a surprise guest on one of Mike’s shows at the Beacon Theatre, where Mike observed after the show that everything Rachel said in the green room could be a bit. Now, on the heels of her Netflix special Big Guy, and in her third appearance on Working It Out, Rachel spills all the details about living with other comedians, the time she moved in with a Bengali family she met on a bus, and all the red flags she ignored in her previous relationships. Plus, Mike shares an unflattering movie offer he received and Rachel defends her pre-schooler’s permanent record.