Episodes

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. p…

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 com…

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

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…

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 d…

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 …

Ronny Chieng, one of the earliest and most popular Working It Out guests, makes a triumphant return. Ronny and Mike discuss the significance of Ronny’s chic onstage wardrobe, the similarities between practicing law and performing comedy, and whether or not it was Ronny who planted the Hasan Minhaj …

Rosebud Baker’s first appearance on Working It Out was in 2021. Since then she’s become a writer on SNL, written for That Damn Michael Che, and become a parent. Now Rosebud returns to talk with Mike about how being a parent affects comedy, and they dispel certain attitudes about filming a comedy sp…

John Early, recently nominated for an Emmy and a Critics Choice Award, sits down with Mike for the first time since the two of them appeared as brothers in Taylor Swift’s, “Anti-Hero” music video. The two discuss avant-garde comedy, Brittany Spears impressions, and what it means to express earnest …

We’ve created an episode for all of you making long car trips or taking long jogs or stretching out on your long beloved couch. It’s our best moments of 2023 episode! It includes Ray Romano’s take on marriage, a joke from Ramy Youssef’s funniest uncle, Rachel Feinstein’s pitch perfect impression of…

Mike welcomes back to the podcast comedian Beth Stelling, whose Netflix special If You Didn’t Want Me Then is on seemingly everyone’s best of year lists, including Mike’s. Mike and Beth discuss touring together, Beth’s desire to be authentic on stage, and Beth’s dad feeding raccoons out of a trough…

Jimmy Carr is one of the most successful comedians in the entire world. On the heels of playing Carnegie Hall and heading out to hundreds of concert dates across many continents, Jimmy Carr returns for another episode of Working it Out. Jimmy and Mike discuss the benefits and pitfalls of dark humor…

Mike welcomes back three-peat guest Joe Birbiglia to celebrate the premiere of Mike’s new Netflix comedy special The Old Man and the Pool. Mike and Joe discuss the four year development of the show, share memories about the Worcester, Massachusetts YMCA pool, and share the funniest jokes that didn’…

Mike’s new special, “The Old Man & The Pool” is finally on Netflix and he brings on an all-timer to celebrate. Pete Holmes returns for a third Working it Out, and he and Mike roast each other as hard as only old friends can. Mike and Pete discuss Pete’s new Netflix special “I Am Not For Everyone,” …

Jo Firestone joins Mike for her second appearance on Working it Out. In addition to just being named the head writer of the newest late night show on network TV, Jo just published a comedic murder mystery called “Murder on Sex Island” and proclaims she is *nothing* like the book’s protagonist even …

On the heels of the release of his new special “Domestic Shorthair,” Todd Barry sits down with Mike this week for a conversation about his 35 years in comedy. The two talk about whether or not Todd invented crowdwork, if Bill Burr was right when he said Mike was “doing” Todd when Mike was first sta…

Ramy Youssef was one of the first and most popular guests on Working It Out back in 2020, and now he’s back with updates to some of the same very material he worked out the first time around. Mike and Ramy discuss which Death Cab For Cutie songs make Ramy cry, unfriendly encounters in Jacksonville,…

25 years ago, Mike won Georgetown University‘s funniest person on campus contest. This week's guest Gary Simons won it three years ago. Now, Gary has been opening for Mike’s new tour and has a lot of questions: How do I get an agent? How do I go from doing 5 minutes to doing an hour? Any relationsh…

Comedian Greg Warren is one of Mike’s oldest friends in comedy. Greg and Mike often work out jokes on the phone but today they bring their collaborative friendship to the podcast for an hour-long discussion on setups, punchlines, and what makes a good partner to work out jokes with. All that plus G…

Mike and Gary Gulman have been friends for a long time, but what kind of friends? Real friends or just work friends? Gary returns to the podcast and he and Mike evaluate the true level of their friendship. Plus they discuss vulnerability in comedy, unhappiness vs. depression, and the advice that Ga…

Comedian Nimesh Patel joins Mike this week for a joke-filled conversation about how to find your comedic voice, how to turn your saddest stories into standup, and whether or not Buddhism and comedy can peacefully co-exist. Plus, Nimesh goes deep on the infamous time he was yanked off stage at Colum…

Hasan Minhaj was one of the first guests on Working It Out back in 2020 and it remains one of the most popular episodes because of Hasan’s natural inclination to work out bits. Off-air Mike and Hasan often trade notes and ideas and today it spills into the podcast. Hasan compares comedy craft to St…

Joe “Joey Bag O’ Donuts” Birbiglia returns to the podcast. Last time, Mike and Joe broke down what it’s like to work together as brothers. Now, in honor of Mike’s upcoming Christmas shows in Boston, they share their favorite Christmas and Boston memories—from the time Joe broke the news about Santa…