Mike’s creative collaborator and director Seth Barrish returns for a special episode of Working It Out announcing the UK premiere of “The Old Man and the Pool” at the Wyndham’s Theatre in London as well as the Edinburgh Fringe Festival in August. Mike and Seth share their excitement about bringing the show across the pond, and Mike expands on his New York Times piece “6 Tips For Bringing Your Solo Show to Broadway,” using it as a jumping off point for a discussion about creativity, writing, and performing. Plus, jokes and stories about New York City overheards, and the time Mike performed a sh ..read more

Chris Gethard: Don’t Think Twice About Being Naked (Recorded October 2022) Mike has seen Chris Gethard naked. So has the cast and crew of Mike’s film Don’t Think Twice. Chris shares his memories of being nude on set, as well as why he was reluctant to return to the world of improv for the movie. The two longtime friends tell stories about touring together and brainstorming their respective projects simultaneously: Don’t Think Twice and Chris’s solo HBO special Career Suicide. Please consider donating to the Natural Resources Defense Council ..read more

When Mike became obsessed with the series “The Last of Us” on HBO he had questions. And he went straight to the source. This week Mike welcomes the writer/producer/director Craig Mazin, who co-created the" The Last of Us," starring Pedro Pascal and Bella Ramsey. Spoiler alert. If you haven’t seen "The Last of Us," be warned, there are spoilers in this discussion. There’s also a lot of advice and insight about screenwriting and storytelling. Craig is a screenwriting sage— in addition to co-creating "The Last of Us" and "Chernobyl"— he also hosts the podcast ScriptNotes with fellow screenwriter ..read more

Iliza Shlesinger: When You're Hot Forever (Recorded October 2022) Iliza Shlesinger is one of the most prolific comedians on the planet, with six specials including her latest, Hot Forever, and a new comedic memoir, All Things Aside. Mike and Iliza bond over their hard-to-pronounce last names, Iliza explains why she doesn’t like being described as “brash,” and we learn why Iliza was born to work out jokes. Please consider donating to Team Rubicon ..read more

Ray Romano has an iconic sitcom and a celebrated stand-up career under his belt, so what drives him to keep challenging himself artistically? Mike and Ray, who often follow each other at the Comedy Cellar, ponder the complicated answer to that question. Plus, discussion of comedy craft, joke-writing technique, and the two separate times Ray was held up at gunpoint. Please consider donating to Harvest Home ..read more

Mike and Bert Kresicher have known each other a little bit for a long time. Now they sit down for an in-depth chat about how to develop a story for standup, why Florida is so strange, and why Bert decided to change the course of his comedy career. Plus, they discuss their shared love for legendary comedic storyteller David Sedaris. Please consider donating to St. Jude Children's Research Hospital ..read more

Chloe Fineman: The SNL Star Who Can Literally Do Anything (Recorded October 2022) Chloe Fineman’s first TV appearance was doing bird calls on Letterman. Now she plays a multitude of beloved characters on SNL and a role in Noah Baumbach’s  film White Noise. Mike and Chloe discuss how she got noticed with her celebrity impressions on Instagram and what happens when you talk smack about Chloe’s dog. Plus, jokes and stories about anesthesia freakouts and celebrity orgasms. Please consider donating to Best Buddies International ..read more

Comedian Alex Edelman returns to the podcast for a victorious third visit, as his award-winning solo show Just For Us heads to Broadway. Mike and Alex defend the merits of kids jokes as well as vaudeville-style wordplay. Plus, a heated debate about the Boston accent which stems from a simple question: How do pronounce the word “room”? Please consider donating to The Jimmy Fund ..read more

Following Nick Kroll’s appearance on Working It Out, Mike revisits his conversation with Nick from October 2018 on his first podcast The Old Ones. The two friends discuss Nick and John Mulaney’s "Oh, Hello on Broadway,” and they reminisce about the time they hosted an a capella festival after smoking something usually only consumed by audience members at an a capella festival. Please consider donating to the Natural Resources Defense Council ..read more

Nick Kroll and Mike met in college and started doing improv and sketch comedy together. Since then, Nick has become a comedy superstar, from his Comedy Central series Kroll Show, to Oh, Hello, to the animated series Big Mouth and Human Resources, to roles in films like Don’t Worry Darling and the Hulu series History of the World Part II. Now the old friends sit down for a candid conversation about Nick’s new projects, memories from their college improv days, and how comedy benefits from silliness. Plus, Nick shares a gem of a story about F. Murray Abraham from his and John Mulaney’s legendary ..read more