Mike welcomes back comedian Gary Simons, who, since his last appearance on the podcast, opened for Mike on his latest tour, had a few of his stand-up bits go viral, and has been performing at the Comedy Cellar. Now, Mike and Gary answer listener questions from people who have taken the leap into stand-up comedy and are looking for advice about how …

This week PDD returns to the podcast a year and a half after originally coming on. Since then, Mike and the boys have started a monthly improv show called “Please Don’t Birbiglia” at UCB. The group talks about what it’s like to improvise together, the unsparing roasts PDD did of Mike when they opened for his show "The Good Life," and the creation o…

Ira Glass has appeared on the Working It Out podcast three times before, and usually it’s Mike asking Ira for advice, whether it’s about podcasting or storytelling. But now the tables have turned: Ira recently listened to a stand-up set he performed years ago, he has the itch to try it again, so he’s come to Mike for comedy advice. On this episode,…

Zarna Garg first appeared on the Working It Out podcast in 2022 and since then her popularity has continued to rise. Zarna explains to Mike how she has built her comedy career like a business, and why performing for an audience of one or two is no different for her than performing for an audience of thousands. Mike and Zarna discuss free speech in …

After decades of being a beloved comedian’s comedian Jessica Kirson has broken out in the last few years with viral crowd work videos and a brilliant new special on Hulu called “I’m The Man.” Mike and Jessica dig deep into the nuts and bolts and emotional work of being a stand-up comic, including overcoming stage fright and dealing with hecklers. J…

This week the legendary Ahmir Thompson (aka Questlove) sits down for his first appearance on Working It Out. Mike and Questlove discuss touring with his father’s band as a kid, every DJ’s worst nightmare, and how jealousy and self-sabotage can affect even a member of a band as iconic as The Roots. Plus, what it was like accepting an Oscar after The…

Rachel Feinstein recently appeared as a surprise guest on one of Mike’s shows at the Beacon Theatre, where Mike observed after the show that everything Rachel said in the green room could be a bit. Now, on the heels of her Netflix special Big Guy, and in her third appearance on Working It Out, Rachel spills all the details about living with other c…

This week Andrew Schulz comes on the podcast and Mike and Andrew break apart why the two of them are unlikely work friends. They discuss Andrew having Donald Trump on his podcast, Andrew’s new deeply personal Netflix special, “Life,” and the politics of free speech in comedy. Plus, Andrew reveals the guest he regrets having on his podcast, “Flagran…

Comedian Josh Johnson is a writer and correspondent for The Daily Show and his stand-up sets have millions of views on YouTube. Josh talks with Mike about cultivating a fan base via the YouTube videos, why he thinks chasing success in the comedy industry is sometimes antithetical to the art form, and shares the advice he got from Trevor Noah. Plus,…

At the top of this Best of WIO episode featuring Elizabeth Gilbert, Mike reads a new piece that he wrote for Elizabeth's Letters From Love Substack. (Recorded November 2024) Author Elizabeth Gilbert wrote one of Mike’s favorite books about creativity, Big Magic. She also wrote a book that, to her surprise, become a cultural phenomenon: Eat, Pray, L…

For this all-new Working It Out Q&A, Mike fields listener questions about people fainting at his shows, how to write comedy about topics that are painful to you, and balancing a day job and creative life when starting out. If your question didn’t get answered on this week’s Q&A, stay tuned for another one soon where Mike answers the rest! Got a new…

Pete Holmes returns to help Mike punch up some last minute jokes before the premiere of Mike’s show The Good Life at the Beacon Theatre in New York. What follows is a heated debate about puns, an attempt to define and dissect the nature of “clean” comedy, and, yes, a nuts and bolts joke writing session. Plus, Pete psychoanalyzes the state of Massac…

This week, the great Nathan Lane returns to Working it Out. Nathan recounts moments from his legendary career — discussing what it was like to work with Mike Nichols, Elaine May, and Robin Williams. He shares what he likes most in a director, who he’s jealous of, and what he remembers of twenty-something year old Mike. Plus, an incredible story abo…

This week Rory Scovel returns to the podcast with his review of how doing a year of completely improvised stand-up went. Mike and Rory dive into the creative process and their own fears on stage, why Rory is jealous of other comedians, and why someone being married to a comedian is hard because every day that comedian has a “presentation at work.” …

Working It Out fan favorite Hasan Minhaj returns for a third episode. Mike and Hasan discuss the enduring memories of childhood crushes, an obsession with who was the fastest in elementary school, and why comedy and politics move in cycles. Plus, Hasan keeps Google Image searching Mike, and Mike invites himself along on a hangout with Hasan’s high …

This week Mike sits down with Severance’s very own Ben Stiller and Adam Scott. The three of them dig into the behind the scenes of Severance Season 2 and discuss what it is that makes them work so well together as actor and director. Ben and Adam share audition advice for actors, as well as how their grieving processes influenced their work togethe…

Matt Rogers is a beloved comedian, writer, actor, and co-host of cult hit podcast “Las Culturistas.” Matt sits down with Mike for a chat about the ups and downs of show business, the inside of writing for a hit TV series, and what it was like when Matt and his podcast co-host Bowen Yang were both invited to audition for SNL. Matt also discusses why…

This week the legendary Stephen Colbert returns to the podcast. Mike and Stephen discuss the behind-the-scenes of Stephen’s Late Night job as well as his Chicago improv days. Stephen talks wisdom passed down to him by David Letterman, Del Close, and Mike Nichols, and shares what makes him cry most easily. Plus, Stephen’s thoughts on meeting George …

This week Mike has all-timer David Sedaris back on the podcast. Sedaris, of course, wrote Naked, Me Talk Pretty One Day, and Holidays on Ice, among other classics. The two discuss where the truth lies in autobiographical non-fiction, fact-checking comedy at The New Yorker, and how to navigate storytelling when it's all too personal. Plus, David pla…

In this special episode of Working It Out, Mike’s old friend and frequent guest Pete Holmes sits down for a holly jolly discussion about classic and new classic Christmas movies. Mike and Pete sing the praises of Elf, examine the dark underbelly of A Christmas Story, and take the Gremlins to task over their many nonsensical rules. Plus, Pete breaks…

Hot off her new Netflix special Crushing It, Fortune Feimster sits down with Mike for a candid chat about telling personal stories on stage, dealing with audience complaints, and Fortune’s coming out journey. Fortune also explains her dynamic with her Handsome podcast co-hosts Tig Notaro and Mae Martin, and she and Mike discuss why fancy doorbells …

Mike welcomes back one of most referenced guests in Working It Out history, the legendary Maria Bamford. Mike and Maria discuss the importance of true confession in stand-up comedy, the financials of being a comedian, and why Maria works out new material one on one with strangers on coffee shops. Plus, Maria’s impression of Esther Perel, and why fi…

Working It Out Hall of Famer Gary Gulman returns to discuss his upcoming Off-Broadway show Grandiloquent. Mike and Gary break down, first of all, what “grandiloquent” means, and how the new show that looks back on Gary’s early life and looks ahead at the prospect of Gary becoming a father. Mike and Gary also check in on their friendship progress, m…

Author Elizabeth Gilbert wrote one of Mike’s favorite books about creativity, Big Magic. She also wrote a book that, to her surprise, become a cultural phenomenon: Eat, Pray, Love. Mike and Liz discuss the unexpected impact of Eat, Pray, Love, and what it was like for Liz to watch Julia Roberts portray her on the big screen. Liz gets candid about t…

In this Working It Out Q&A Mike breaks down the development of the New York City finale of his show The Good Life. He explains the evolution from Please Stop The Ride to The Good Life. Plus, he answers your questions about embarrassment, fear, jealousy, and inspiration. Get tickets to The Good Life at the Beacon Theatre…