This week, the hilarious Chloe Troast joins Mike to answer listener-submitted questions. The two discuss what to do when an improv scene goes off the rails, Chloe’s relationship to comedy after SNL, and how being around other talented people makes everyone better. Plus, Chloe shares the “truth “about the Please Don’t Destroy boys. See Chloe in Pepper Slit Live in Her Living Room Please consider donating to Jenni's Rescue Ranch Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Working It Out favorite Jo Firestone returns for a triumphant fourth appearance, this time pregnant and rocking a Phantom of the Opera Toronto production t-shirt. Jo talks with Mike about pregnancy, her “shotgun wedding” at city hall, and her new book Sex on Murder Island, the sequel to Murder on Sex Island. Plus, much talk of Lord of the Rings, including why Jo relates to Frodo and why Mike sympathizes with Gollum. Subscribe to Working It Out Premium on Apple Podcasts for a special *extended version* of this episode!

(Recorded January 2026) 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 John’s career changed after having kids. They work out new jokes about the time John asked Mike to go skydiving, getting yelled at by substitute teachers, and a story about an interaction with Frank Sinatra that—until Mike tells it on stage—John cannot find peace. Plus, John brings a literal buzzer into the interview so that he can hit it if he finds Mike guilty of a certain tendency.

Michelle Buteau was a local TV news editor in New York until she tried stand-up for the first time, only days after 9/11. Since then she’s become an international touring comedian, bestselling author, and co-creator and star of her own Netflix series Survival of the Thickest. Now Michelle talks with Mike about figuring out who you are as a person, sharing embarrassing personal stories in a writers room, and why comedy is a family business. Plus, new jokes about parenting, yoga class, and Mike and Michelle discuss whether Mike should go on the Breakfast Club morning show.

This week, SNL’s Jane Wickline and comedian Liva Pierce return to Working It Out to discuss the Off-Broadway debut of their two person musical comedy show, Dukes. Mike grills Jane and Liva on the realities of working so closely with another person, and the three of them break apart the existential dread that accompanies most of their creativity. Plus, Jane and Liva work out two new songs from their show and the three of them create a song from a bit Mike is working on. Please Consider Donating To: Survived and Punished NYC  See Jane and Liva Off-Broadway in Dukes. Get tickets here. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

(Recorded August 2025) Having recently toured together with John Mulaney, 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.

Comedian Aaron Chen may be known internationally for his role on the hit Australian TV series Fisk, but he’s been a working stand-up since the age of 15. In fact, he might be the only Working It Out guest who learned to drive commuting to and from comedy clubs with their dad. Now he’s got a hit Netflix special, Funny Garden. This week, Aaron sits down with Mike to discuss his journey from the suburbs of Sydney to opening for Ali Wong to headlining his own shows across the world. Plus, Aaron and Mike open up about the instances early in their careers when they regrettably lashed out at audiences, and how they became more adept at navigating difficult shows.

This week, the very funny Jon Rudnitsky joins Mike to answer listener submitted questions. The two of them discuss how long it was before they started earning money from comedy, the complete loss of dignity required to make it as a stand-up, and what it is that keeps them showing up every day. Plus, how Jon caused what he believes to be one of the greatest mistakes in SNL history.

Wanda Sykes is one of Mike’s original dream guests for the podcast. Now, on the heels of her new Netflix special, Legacy, Wanda talks with Mike about how they both started in DC, and why Wanda left her job at the NSA to pursue a career in stand-up comedy. Wanda tells the story of how she moved from the writers' room of The Chris Rock Show to acting in sketches, how she got tricked into auditioning for Curb Your Enthusiasm, and the weird requests she gets from Curb fans. Plus, new jokes from Mike and Wanda.

Filmmakers Phil Lord and Chris Miller’s resume is a laundry list of hits: Project Hail Mary, The Lego Movie, 21 Jump Street, Spider-Man: Into the Spider-Verse, and more. Their success with projects that didn’t initially seem like good ideas has even spawned a verb in Hollywood, “to Lord and Miller” something. Now they sit down with Mike to discuss the positive and negative ramifications of that. They also discuss the test screening process of Project Hail Mary, and working with Nicolas Cage on their new series Spider-Noir. Plus, they reveal the five films that would be on the syllabus of Lord and Miller University.