Best of WIO: Questlove (Recorded April 2025) 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 documentaries Sly Lives! and Ladies & Gentlemen... 50 Years of SNL Music.

This week the one and only Sebastian Maniscalco sits down with Mike for a wide ranging conversation on their parenting strengths and weaknesses, the difference in what makes them cry, and Sebastian’s early days waiting on his future co-star Robert DeNiro. Plus, Sebastian reveals if he ever acts like Sebastian offstage.

This week Mike sits down with Julio Torres to talk comedy writing and color theories. Based on ideas posited in Julio’s new Off-Broadway solo show, Color Theories, the two of them get to the bottom of what color Barbie the Movie, Martha Stewart, and Jeremy Strong are. They also discuss the behind-the-scenes story of Julio’s viral SNL sketch, “Papyrus” starring Ryan Gosling. Plus, two encounters Julio and Mike had at the gym that aren’t sitting right with them.

Comedian and SNL writer KC Shornima might be the only Working It Out guest who has climbed Mount Kilimanjaro. KC and Mike get to the bottom of why she thrives in stressful situations like mountain climbing, camping on a glacier, and writing for Weekend Update. Mike asks KC some questions from her bosses, Michael Che and Colin Jost, and KC explains why she feels compelled to talk about difficult topics on stage. Please note: This episode contains discussion of sexual assault.

Three years ago, comedian Ryan Hamilton was hit by an airport shuttle bus. Two years ago, Ryan came on Working It Out to talk about the experience. Now, he returns to explain how he learned to talk about the traumatic event on stage and find the humor in the pain, which included buying weed with his mom during his recovery. Ryan also breaks down the daily routine of touring with Jerry Seinfeld, and shares the blunt advice he got from Chris Rock.

(Recorded January 2025) 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.

Fresh off a few gigs featuring on John Mulaney’s new tour, Mike and Fred sit down for his first in-studio appearance on Working it Out. They discuss Fred’s SNL audition, his best sketch writing advice, and the manners of navigating video exhibits in museums. Plus, Fred borrows Mike’s guitar to demonstrate how cultures around the world play the acoustic guitar.

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.