Episodes

Mike welcomes author, actor, and filmmaker Cazzie David to the podcast and right away, Mike challenges the notoriously misanthropic Cazzie to list five things she loves. It takes a while. Then, Cazzie breaks down her new book...

Working It Out all-timer Taylor Tomlinson returns to the podcast this week on the heels of the release of her new Netflix special, “Prodigal Daughter.” Mike and Taylor talk through what they do when they get stuck on a bit, w...

Ali Siddiq is one of the most prolific storytellers in comedy. Although they work in a similar format, Ali and Mike’s paths have never crossed until now. Now they sit down to discuss the nuances of comedic storytelling, inclu...

Beloved British comedian James Acaster and Mike have never met but they have a lot in common, including brushes with death early in their lives that influenced their comedy. James and Mike discuss James’s experience with heck...

Best of WIO: Bob Odenkirk (Recorded July 2025) 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 …

Connor Ratliff is a beloved cult comedy figure known for his award-winning podcast Dead Eyes and his long-running live show/YouTube series The George Lucas Talk Show. He also played an improv student in Mike’s film Don’t Thin...

Heidi Gardner went from being a hairdresser in LA to joining the Groundlings to 8 seasons on SNL, where she created characters like “Dianne, The Mom Who's Only Read About New York on Facebook” and “A Woman Who Insists She's N...

For the 200th episode of Working It Out, Mike sits down with one of his oldest friends and one of the podcast’s first ever guests, John Mulaney. The two discuss monkeys wearing space suits, old stories from the road, and how ...

This week Mike sits down with comedian Jordan Jensen. A master of turning taboo topics into comedy- as seen in her Netflix special Take Me With You- Jordan explains how her fearless, no filter stage persona coexists with her ...

This week, SNL’s Sarah Sherman returns on the heels of the release of her new HBO special, “Live + In the Flesh.” Sarah and Mike discuss why Sarah goes to therapy three times a week, which SNL cast member Sarah is jealous of,...

Best of WIO: Stephen Colbert (Recorded January 2025) This week the legendary Stephen Colbert returns to the podcast. Mike and Stephen discuss the behind-the-scenes of Stephen’s Late Night job as well as his Chicago improv days. Stephen talks wisdom passed down to him by David Letterman, Del Close, …

Best of WIO: Josh Johsnon (Recorded March 2025) Comedian Josh Johnson is a writer and correspondent for The Daily Show and his stand-up sets have millions of views on YouTube. Josh talks with Mike about cultivating a fan base...

Natalie Palamides is a writer and performer best known for her avant-garde comedy shows Laid, Nate, and WEER. She’s eaten raw eggs on stage, fondled audience members (with their consent), and played both halves of a feuding c...

Mike started this podcast so that one day Michael Che would come on. Today is that day. In this all-timer episode, Mike and Che work out tons of jokes and discuss the advice Lorne Michaels gave to Che that he’ll never forget,...

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 ...

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 ...

The last time comedian Vir Das was on Working It Out, he and Mike discussed the intense reaction to a piece he performed called “Two Indias.” Now Vir returns to share how he moved on from the controversy, and all the ups and ...

On the heels of her new special “Unspeakable Things,” Leanne Morgan joins the podcast this week to talk Southern beauty shop gossip, getting started in comedy selling jewelry door to door, and in what way Mike is “her Elvis.”...

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...

This week poet J. Hope Stein & Mike’s wife ‘Clo’ returns to the podcast. Jen reads original poetry that Mike uses as inspiration for his bits—and the two dispute whose side of the story is being told in each. Mike and Jen dis...

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 Wo...

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...

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...

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…