Arthur Brooks might be the only Working It Out guest who's crossed paths with Jerry Seinfeld, Oprah Winfrey, and the Dalai Lama. He’s a professor and bestselling author, whose books include The Happiness Files, From Strength to Strength, and Build the Life You Want, which he co-authored with Oprah. Mike sits down with Arthur, whose speciality is the science of happiness, to explore what goes on in the brains of comedians and audiences at comedy shows. They discuss creative productivity, how Arthur prepares his lectures, and the benefits of gratitude.

This week, Pete Holmes returns to the studio for one of Working It Out’s most joke-dense episodes ever. Mike and Pete work out jokes about strangers in hot tubs, why Jerry Seinfeld sounds like his own name, and how cool guys in movies swallow their pills without water. Plus, the comedy advice Pete wishes he knew when he was starting out. Want more of Mike and Pete? Subscribe to Working It Out’s premium feed on Apple Podcasts to listen to their bonus episode together where they work out listener-submitted material!

Todd Glass was one of the first comics Mike opened for. It’s easy to see how, since then, Todd has become one of the most beloved comic of his generation, revered by comics including Nikki Glaser, Judd Apatow, and Rory Scovel. Now Mike and Todd sit down for a discussion about how coming out changed Todd’s life and his comedy, Todd’s heart attack backstage at Largo, and Todd’s new live show featuring a band. Plus, jokes about peanut allergies and old-sounding names, and the story behind the viral video of Todd vs. a heckler.

Mike met Nick Offerman years ago at the Sasquatch! Music Festival in Washington state, which is fitting because Nick is a man of nature, almost as well known for his woodworking as he is for his acting. After examining the Working It Out studio table, Nick tells Mike about what it was like to act as the straight man to Amy Poehler on Parks and Rec, and more recently prep for his drama

Comedian Caleb Hearon just turned 30 and he’s already got an hour-long HBO special, hosts a hit podcast (So True with Caleb Hearon), and was named one of the top social media influencers of 2025 by Rolling Stone. But it hasn’t been an easy road. Caleb talks with Mike about his battles with suicidal ideation, how improv comedy saved his life, and how he drew on the passing of his estranged father for his comedy special. Plus, Caleb and Mike discuss the value seeing stand-up live vs. on TV, and come up with a plan to go off the grid and live in a cabin in the mountains together.

The great Jenny Slate joins Mike this week for a wide-ranging conversation about getting hypnotized after being fired from SNL, a graduation speech Jenny gave to a class of one person, and making art to feel less lonely. Plus, jokes and stories about seeing your friends naked, improv classes for the elderly, and the time Jenny’s faked case of appendicitis went too far.

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.