Mike welcomes back the poet J. Hope Stein, aka Jenny, aka Clo, aka Mike’s wife of fifteen years. A frequent collaborator on Mike’s comedy specials and movies, Jenny describes her favorite type of creative feedback and why she’s most impressed by poetry that crosses over to audiences who don’t always understand poetry. The couple shares candid and embrassing stories from the early days of their romance including two stories that might make it into Mike’s new live show. Plus, Jen reads two new...

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.

On the heels of the release of his new special “Just For Us” on Max, Alex Edelman returns to the podcast for the fourth and best time yet. Mike and Alex break apart the story of the time Alex’s bank lost all his money, how a protestor recently disrupted his show, and what it feels like to be releasing his special after the death of his beloved director, Adam Brace. Plus, Alex’s recent and very strange run-in with Bill Gates. Please consider donating to: https://www.sefaria.org/texts

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.

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?

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.

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 why Chris’ “worst gig” story involves an actual knife at his throat.

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:...

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...

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...

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.

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 New Yorker story after all. Plus, why Ronny absolutely refuses to reveal his actual birthday. Please consider donating to APIAVote

Ray Romano: Sometimes the Setup is the Punchline (Recorded May 2023) 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.

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 special while pregnant. Plus, the art of pitching ideas for different types of sketch shows, and why Rosebud’s daughter has to call her grandfather “Mr. Baker.”

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 despair in John’s new Max special, “Now More Than Ever.” Plus, the time John ran away after coming out to his best friend. Please consider donating to: https://www.nationalnursesunited.org/pac

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 her husband, and deep confessional moments about Mike’s friendships with Tom Papa and Gary Gulman. Plus, Ira Glass’s diagnosis to not just work out Mike’s jokes but to work out Mike’s life.

Working It Out will be back on January 1. This week, we’re sharing an episode of The Sarah Silverman Podcast, from our friends at Lemonada Media. Sarah hates men’s cologne and wants you to STOP. IT. Plus, she offers advice on setting ground rules for a threesome, reacts to a child who’s obsessed with her hooky-ass song, “Night Bra,” and recounts a special moment on stage with her sister, Laura. To hear more of Sarah’s show, head to https://lemonada.lnk.to/sarahsilverman

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. Plus, they explore the parallels between stand-up comedy and Beth’s new venture: professional field hockey.

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, what Jimmy discovered from several public cancellations, and why sometimes the goal is simply to get better than you were last year. Plus, what ever happened to ordering just a slice of...

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’t make it into the special. *Should* they have made it into the special? Joe thinks so. You be the judge. Plus, Mike answers listeners’ questions about the special.

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,” the problem with Micheal Jackson’s nickname “Wacko Jacko,” and what secrets Pete has in store for his next hour of comedy. Plus, Pete literally won’t stop doing impressions: Bill Burr, Jerry...

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 though the similarities are striking. Jo also explains why there’s so much dust in her purse, and posits that the scariest part of haunted houses aren’t actually the jump scares, but rather the...

Taylor Tomlinson Returns: She's Not Like Us(Recorded March 2022) The last time Taylor Tomlinson was on "Working it Out," she had just released her first Netflix comedy special Quarter-Life Crisis. Now, Taylor returns on the heels of her latest special Look At You. Mike and Taylor discuss why Look At You is even more vulnerable than Quarter-Life Crisis, and how many years it takes to become yourself on stage. Plus, they work out new jokes about Mike’s irrational goal to seem “cool” to his...