Chicago improv performer and teacher Liz Allen taught a workshop for Mike’s college improv group almost 25 years ago. Since then, Mike and Liz have found numerous ways to reunite and collaborate, most notably on Mike’s film Don’t Think Twice. Now Mike sits down for an in-depth chat with one of his favorite improvisers about the unique roots of Chicago improv, Liz’s (in)famous teacher Del Close, and the one-in-a-million coincidence that connected Liz and Gillian Jacobs. Please consider donating to Stepping Stones Network Check out https://www.lizallenimprov.com for more info about improv coac ..read more

Mike sits down with comedian, actor, and writer Esther Povitsky to discuss her special Hot For My Name. Mike has a lot of questions about the time Esther crashed her fiancée's bachelor party in Vegas. Plus, Esther figures out Mike’s attachment style, and they discuss the differences between the LA and New York comedy scenes. All this, and jokes about adults dressed as babies, watching OnlyFans with your partner, and being outed as a comedian on the subway. Please consider donating to Rheumatoid Arthritis Foundation ..read more

Mike sits down with the legendary comedian and writer Seth Meyers for a conversation that reveals who is secretly the funniest of the funniest at SNL behind-the-scenes and who was the most popular Strike Force Five host. Then, Mike and Seth work out new material about serial killers, the D.A.R.E. program, and dropping acid in Amsterdam. Plus: who will take over for Lorne Michaels after he leaves SNL? Please consider donating to Sanctuary For Families ..read more

Mike became an instant super-fan of Ilana Glazer in 2014 when her hit series Broad City premiered on Comedy Central. This week on the podcast Mike and Ilana go deep on the origins of Broad City, Mike’s cameo on the show, honest takes on parenting, the development of Ilana’s new hour of stand-up comedy, and how *Broad City* Ilana is different from *real life* Ilana. Plus, jokes and stories about weed-induced anxiety and saying hello to strangers. Please consider donating to Out of the Closet ..read more

This week Mike responds to listener questions. How many of your stories are true?  Who is your dream guest? What is your greatest piece of comedy advice? All these and more ..read more

This week Mike welcomes Comedy Cellar friend and comedy star Chris Distefano. Chris’s shares important lessons in failure: how a bad set got him booked on Letterman, and the advice his wife gave him about not listening to studio executives. Mike and Chris also dissect Chris’s famous 9/11 story, and why Chris’ “worst gig” story involves an actual knife at his throat. Please consider donation to the Tunnel to Towers Foundation ..read more

Mike welcomes Ben Marshall, John Higgins, and Martin Herlihy, aka Please Don’t Destroy, known for their wildly popular shorts on SNL. Mike is determined to get Martin to talk more than he did on Pete Holmes’s podcast. The group shares what they like and dislike about each other, and break down what it’s like to be both sketch writers and filmmakers on SNL. Plus, what it’s like to work with Bad Bunny in a Shrek costume and get roasted by Taylor Swift. Please Consider Donating To: Meals on Wheels ..read more

Jim Gaffigan: Dark Comedy From the Cleanest Comedian (Recorded July 2023) Mike met Jim Gaffigan in 1997 when he cold-called Jim’s New York City landline. Jim appeared as a guest on Working It Out in 2021 and now, between touring with Jerry Seinfeld, releasing his 10th comedy special “Dark Pale,” and raising money for the Georgetown Scholars Program, Jim sits down with Mike in-studio for his second Working It Out chat. The old friends go deeper as they work out material and discuss how Jim actually *doesn’t* like hot pockets, what item of clothing comedians should never wear, and why being mar ..read more

Roy Wood Jr makes a triumphant return to the podcast and he and Mike pick up right where they left off. The two old friends discuss the evolution of unconnected jokes into a more cohesive whole hour of stand-up. They discuss why Mike, Neal Brennan, and Chris Rock are all pressuring Roy to go even deeper with his new material about his dad. Mike and Roy break down the best bits from Roy’s new special Imperfect Messenger, and Roy shares two all-timer stories in the slow round. Plus, Roy gets candid on exactly why he may or may not be hosting The Daily Show. Please consider donating to I See Me ..read more

Maddie Wiener started performing stand-up at age 16. Now, at age 25, she headlines clubs, is a fixture at the Comedy Cellar, and  she was recently a special guest on Mike’s shows at The Wilbur in Boston. Now Maddie and Mike sit down for a chat about the relationship between anxiety and comedy, and Mike helps Maddie develop a story about a panic attack. Plus, the wisdom Maddie learned from Nikki Glaser, and why “Hey, can we talk?” is the scariest text you can get. Please consider donating to Liberation Library ..read more