Best Iraglass Podcasts (2026)

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Stephen Colbert: A Gift from the Comedy Gods 51:12

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2d ago51:12

51:12

Best of WIO: Stephen Colbert (Recorded January 2025) 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 mos…

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Josh Johnson: Reinventing the Modern Comedy Special 52:32

9d ago52:32

52:32

Best of WIO: Josh Johsnon (Recorded March 2025) 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 …

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197. Natalie Palamides: Wisdom from a Modern Clown 59:01

16d ago59:01

59:01

Natalie Palamides is a writer and performer best known for her avant-garde comedy shows Laid, Nate, and WEER. She’s eaten raw eggs on stage, fondled audience members (with their consent), and played both halves of a feuding couple in a way that has to be seen to be believed. Mike and Natalie discuss how Natalie’s formal training in clowning informs…

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196. Michael Che: An Amateur Therapy Session 1:12:26

23d ago1:12:26

1:12:26

Mike started this podcast so that one day Michael Che would come on. Today is that day. In this all-timer episode, Mike and Che work out tons of jokes and discuss the advice Lorne Michaels gave to Che that he’ll never forget, how Che went from designing and selling t-shirts on the street to being a stand-up comic, and what keeps him coming back to …

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195. Arthur Brooks: The Science of Happiness and Humor 45:25

1M ago45:25

45:25

Arthur Brooks might be the only Working It Out guest who's crossed paths with Jerry Seinfeld, Oprah Winfrey, and the Dalai Lama. He’s a professor and bestselling author, whose books include The Happiness Files, From Strength to Strength, and Build the Life You Want, which he co-authored with Oprah. Mike sits down with Arthur, whose speciality is th…

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194. Pete Holmes Returns: Vulnerability is Everything 1:03:29

1M ago1:03:29

1:03:29

This week, Pete Holmes returns to the studio for one of Working It Out’s most joke-dense episodes ever. Mike and Pete work out jokes about strangers in hot tubs, why Jerry Seinfeld sounds like his own name, and how cool guys in movies swallow their pills without water. Plus, the comedy advice Pete wishes he knew when he was starting out. Want more …

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193. Vir Das Returns: How to Find Your Voice, Literally 54:07

1M ago54:07

54:07

The last time comedian Vir Das was on Working It Out, he and Mike discussed the intense reaction to a piece he performed called “Two Indias.” Now Vir returns to share how he moved on from the controversy, and all the ups and downs he’s experienced since then, including: literally losing his voice just weeks before sold out shows in Mumbai, writing …

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192. Leanne Morgan: In The Presence of a Comedy Angel 42:56

2M ago42:56

42:56

On the heels of her new special “Unspeakable Things,” Leanne Morgan joins the podcast this week to talk Southern beauty shop gossip, getting started in comedy selling jewelry door to door, and in what way Mike is “her Elvis.” Plus, the time Leanne may or may not have been picked up in an SUV by President George W. Bush. Please consider donating to …

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191. Todd Glass: The Ultimate Comic's Comic 59:14

2M ago59:14

59:14

Todd Glass was one of the first comics Mike opened for. It’s easy to see how, since then, Todd has become one of the most beloved comic of his generation, revered by comics including Nikki Glaser, Judd Apatow, and Rory Scovel. Now Mike and Todd sit down for a discussion about how coming out changed Todd’s life and his comedy, Todd’s heart attack ba…

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190. J. Hope Stein: Eavesdropping on the Eavesdropper 58:13

2M ago58:13

58:13

This week poet J. Hope Stein & Mike’s wife ‘Clo’ returns to the podcast. Jen reads original poetry that Mike uses as inspiration for his bits—and the two dispute whose side of the story is being told in each. Mike and Jen discuss helpful vs. unhelpful artistic feedback, the difference between Mike in real life and Mike on the podcast, and Mike has …

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189. Nick Offerman: The Man Behind the Mustache 57:08

2M ago57:08

57:08

Mike met Nick Offerman years ago at the Sasquatch! Music Festival in Washington state, which is fitting because Nick is a man of nature, almost as well known for his woodworking as he is for his acting. After examining the Working It Out studio table, Nick tells Mike about what it was like to act as the straight man to Amy Poehler on Parks and Rec,…

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Caleb Hearon: Improv Saved His Life 1:00:06

3M ago1:00:06

1:00:06

Comedian Caleb Hearon just turned 30 and he’s already got an hour-long HBO special, hosts a hit podcast (So True with Caleb Hearon), and was named one of the top social media influencers of 2025 by Rolling Stone. But it hasn’t been an easy road. Caleb talks with Mike about his battles with suicidal ideation, how improv comedy saved his life, and ho…

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187. Jenny Slate: Unafraid of Sadness 1:10:02

3M ago1:10:02

1:10:02

The great Jenny Slate joins Mike this week for a wide-ranging conversation about getting hypnotized after being fired from SNL, a graduation speech Jenny gave to a class of one person, and making art to feel less lonely. Plus, jokes and stories about seeing your friends naked, improv classes for the elderly, and the time Jenny’s faked case of appen…

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Questlove: The Art of Self-Sabotage 57:24

3M ago57:24

57:24

Best of WIO: Questlove (Recorded April 2025) 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 wa…

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186. Sebastian Maniscalco: What Is He Even Doing Here? 53:51

3M ago53:51

53:51

This week the one and only Sebastian Maniscalco sits down with Mike for a wide ranging conversation on their parenting strengths and weaknesses, the difference in what makes them cry, and Sebastian’s early days waiting on his future co-star Robert DeNiro. Plus, Sebastian reveals if he ever acts like Sebastian offstage. Please Consider Donating To: …

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185. Julio Torres: Off-Broadway, SNL, and Why Barbie Isn’t Pink 47:04

4M ago47:04

47:04

This week Mike sits down with Julio Torres to talk comedy writing and color theories. Based on ideas posited in Julio’s new Off-Broadway solo show, Color Theories, the two of them get to the bottom of what color Barbie the Movie, Martha Stewart, and Jeremy Strong are. They also discuss the behind-the-scenes story of Julio’s viral SNL sketch, “Papyr…

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Announcing Working It Out Premium 0:57

4M ago0:57

0:57

Mike announces Working It Out Premium Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.By Mike Birbiglia's Working It Out podcast

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184. KC Shornima: Get Comfortable With This Darkness 1:04:52

4M ago1:04:52

1:04:52

Comedian and SNL writer KC Shornima might be the only Working It Out guest who has climbed Mount Kilimanjaro. KC and Mike get to the bottom of why she thrives in stressful situations like mountain climbing, camping on a glacier, and writing for Weekend Update. Mike asks KC some questions from her bosses, Michael Che and Colin Jost, and KC explains …

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183. Ryan Hamilton Returns: You Better Have Some Jokes 58:02

4M ago58:02

58:02

Three years ago, comedian Ryan Hamilton was hit by an airport shuttle bus. Two years ago, Ryan came on Working It Out to talk about the experience. Now, he returns to explain how he learned to talk about the traumatic event on stage and find the humor in the pain, which included buying weed with his mom during his recovery. Ryan also breaks down th…

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Ben Stiller and Adam Scott: Working it Innie and Outie 53:07

4M ago53:07

53:07

(Recorded January 2025) 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 thei…

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182. Fred Armisen Returns: Is He Joking? 49:10

5M ago49:10

49:10

Fresh off a few gigs featuring on John Mulaney’s new tour, Mike and Fred sit down for his first in-studio appearance on Working it Out. They discuss Fred’s SNL audition, his best sketch writing advice, and the manners of navigating video exhibits in museums. Plus, Fred borrows Mike’s guitar to demonstrate how cultures around the world play the acou…

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181. Jo Firestone Returns: The Best Stand-Up (Who Doesn’t Do Stand-Up) 51:24

5M ago51:24

51:24

Jo Firestone is a multi-talented writer, actor, and comedian. In her third appearance on Working It Out, Jo explains the thought process behind her experimental live comedy shows, which often involve clay, paper mache, and pie. Jo also delves into the experience of working as the head writer for After Midnight with Taylor Tomlinson and discusses be…

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180. Kumail Nanjiani: Oh, Mary!, The Big Sick, and a Return to Stand-Up 57:36

5M ago57:36

57:36

Kumail Nanjiani is a stand-up comedian, a movie star, and an Academy Award-nominated screenwriter. Now he’s returning to stand-up comedy after a six year break and co-starring as Abraham Lincoln in the hit Broadway show Oh, Mary!. Kumail sits down with Mike to discuss all the twists and turns of his career, including co-writing The Big Sick with hi…

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Q&A: Mike Answers Voicemails About AI and Weird Audience Energy 28:28

5M ago28:28

28:28

For this all-new Working It Out Q&A, Mike fields listener questions about how and why he cuts jokes that he loves, the impact AI might have on comedy, and how to navigate weird or bad energy from an audience. Plus, how to get motived for creative work, and how to restart stand-up comedy after a long pause. Got a question for Mike? Send a voicemail …

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179. Bob Odenkirk: The Art of Anger in Comedy 51:45

5M ago51:45

51:45

Bob Odenkirk was already a comedy legend (SNL, The Ben Stiller Show, Mr. Show with Bob and David) before he took a left turn into dramatic acting with Breaking Bad and Better Call Saul. Now he’s entered yet another new phase as an unlikely action star in films like the Nobody series. Bob sits down with Mike to discuss how anger works in comedy and …