When Jon Laster was last on the podcast in the summer of 2020, Mike and Jon talked race relations in America and the relationship between tragedy and comedy. Now Jon returns to discuss his thoughts on what has changed, what has stayed the same, and how his frustration led him to create an app called Blapp, which helps support black-owned businesses. Plus, stories and jokes about Jon’s mother showing up to watch Jon play basketball on a team he wasn’t on, finding a better word for "billionaire," and why Mike doesn't wear a speedo. Please consider donating to: Jara Check out Blapp and help support black-owned businesses.

Mo Amer started doing stand-up when he was 14, and now he's being introduced by The Rock in his latest Netflix special, Mohammed in Texas. Mike talks with Mo about that journey, growing up Palestinian in Houston and later performing in college lunchrooms. They discuss why immigrants love Nescafe, the lengths to which Mo will go to get access to a bidet, and why it's important for writers to store ideas in a "creative savings account." Please consider donating to: https://www.angelbynature.com/reliefgang

What started as a poem by Sarah Millican about a bad divorce sprouted into one of the most popular comedy careers in England in the last 20 years. Mike and Sarah discuss how hitting rock bottom can lead you to the top and what happened when Sarah’s childhood bully sent her a long letter as an adult. Plus, new bits about Sarah’s husband who may or may not be a robot, Mike’s dad’s excessive use of speakerphone, and that time Sarah got too comfortable with a sharp object. Please consider donating to: https://www.samaritans.org/

Hannah Einbinder received Emmy and Golden Globe nominations for her breakout performance in HBO’s “Hacks.” Today Hannah and Mike discuss what it means to be yourself in auditions, risking rejection in front of audiences, and the miracle that is crowd work. They kick around new jokes about the time Mike’s Apple Watch called the police and what it means to say I love you from the other room. All that, and some deep thoughts on deep sea fish. Please consider donating to: The Trevor Project

In addition to his new hit book “The Anthropocene Reviewed,” John Green has written several novels that have debuted at #1 on the New York Times bestseller list including “The Fault in Our Stars” which was adapted into an indie blockbuster with Shailene Woodley, Ansel Elgort, and featuring Mike in the role of Patrick the youth pastor. Mike and John recount meeting each other on the set of the movie and in the slow round John recalls getting a banana smushed in his face in 4th grade. John helps Mike work new out jokes and they end up in a rabbit hole of summer camp nostalgia. John also becomes the first guest to try to place his own Jack Antonoff music sting. Please consider contributing to: Partners in Health Check out Mike's tour dates at: Birbigs.com

Rosebud Baker can make anything funny. She has jokes about the tragic death of her sister, her own struggles with addiction, and why nurses seem to be a little too cocky. Mike and Rose kick around jokes about what to do when your Uber is filling up with water, how much urine is in a public pool, and why some of us marry our dads. All that, and a story about toasting a U.S. president when she was a kid. https://www.safehorizon.org/

In December Mike presents Alex’s Edelman’s solo show, "Just for Us" off-Broadway at the Cherry Lane Theatre. It's an award-winning comedy in which Alex (who is Jewish) tells the story of being accidentally invited to a gathering of white nationalists & then what happened when he…showed up. Mike & Alex crack open that story as well as working out jokes about rollerblading into museums, why Socrates had a hard time at parties, & how texting the tooth fairy can backfire. https://www.childrensdefense.org/

Legendary British comedian Jimmy Carr begins his conversation with Mike by saying, “I wrote a book in lock-down because it was that or a podcast and I figured a book would be more dignified.” This begins an hour-long chat between friends that jumps from jokes to roasts to a genuine and vulnerable discussion of how laughter has the power to heal us. https://www.smcyouthwork.org/

Fresh off his Emmy win (with stage companion Conan O’Brien) Stephen Colbert joins Mike for a discussion of comedy, anxiety, and why he’ll never run for Senate. He explains that the reason he loves improv is that there’s nothing like failing with someone else and laughing about it with your scene partner, and he explains why Bill O’Reilly was never his scene partner. https://somosamigos.org/

Atsuko Okatsuka makes comedy videos featuring her grandmother & her husband, which Mike is convinced should be a feature film. The two comedians discuss Atsuko’s move from Japan at age 10, her grandmother’s run-in with a praying mantis, and why Mike might end up making a cameo in Atsuko’s feature film singing “Amazing Grace.” Earnestly. https://downtownwomenscenter.org/

Filmmaker Sterlin Harjo co-created the smash comedy hit Reservation Dogs for FX about four Indigenous teenagers growing up on a reservation in Oklahoma. Sterlin tells Mike about the time he accidentally taped over someone's wedding video while applying to the Sundance Film Lab. He also discusses Native representation in film & how his new series may represent some sense of hope. Many laughs. Many challenging topics. A little backstrap. https://wellforculture.com/

The last time Phoebe Robinson and Mike hung out, they were waiting to be picked up by an Uber on the side of a highway after their tour bus broke down. In this episode, they discuss Phoebe’s third book, "Please Don't Sit on My Bed in Your Outside Clothes,” the eternal question "to prenup or not to prenup," and why Mike was qualified to be a token white guy on Phoebe's "Sooo Many White Guys" podcast. https://www.girlswritenow.org/

Mike welcomes back one of our most beloved guests, Pete Holmes, to celebrate the paperback release of The New One. Pete has a lot to say about hardcovers, hardbodies, and how his father asks him questions just he so can answer them himself. Mike calls this "an expert's edition" of Working It Out because the slow round and the new material all swirl into one singular soft serve ice cream comedy cone. https://cac.org/

Randall Park has brought his one of a kind comedic approach to Trainwreck, Fresh Off the Boat, Veep, and the Marvel Universe. Randall reveals how he and Ali Wong scored the Keanu Reeves cameo for their film "Always Be My Maybe." Mike shares a dark version of the children’s joke “Why was 6 afraid of 7?” and Randall explains why collecting turtle figurines is indeed a skill. https://www.kulturecity.org/

Mike met Jim Gaffigan in 1997 when he cold-called Jim’s landline. They went out for, of course, pizza and Jim gave him advice that Mike has not only used but also shares with others. The two comics discuss the insanity of charging large pizza prices for mediums size gourmet pies, deciding not to curse on stage, and what happens when a non-political comedian has had enough. It’s Jim Gaffigan like you’ve never heard him before. https://www.theimaginesociety.org/

For the 50th episode Mike welcomes Kate Micucci, another member of the “Don’t Think Twice” cast. Kate is one half of the folk comedy duo Garfunkel & Oates and her creative talents stretch from music to acting to visual art. Kate shares some of her latest cartoons-in-progress and the two friends go deep on postpartum depression and its lesser known cousin “post-artum depression.“ The episode goes from silly to serious to nostalgic the way the best friendships do. https://826national.org/

In 2015 Mike filmed “Don’t Think Twice” where Keegan-Michael Key played a guy who got cast on a fictional version of SNL. This year Keegan hosted the *actual* SNL in a delightful case of life imitating art imitating life. Today Keegan and Mike nerd out about live sketches vs. filmed Key and Peele sketches, the wisdom of Robert Deniro, and how Keegan seems to be able to do anything, including his most recent role in the new musical comedy series Schmigadoon! https://rfkhumanrights.org/

Judd Apatow recently saw Mike's entire new show in progress, and he's got a lot of feedback. As they break apart Judd's notes, they veer into topics like dark joy vs. light joy, why we exercise, and how many days per week it's appropriate to eat ice cream. Plus, Mike details a serious argument he had with his daughter Oona about dinosaurs. This episode is an all-timer. Judd and Mike are truly working it out. https://826national.org/

You can hear the excitement in Mike's voice as he welcomes legendary author Malcolm Gladwell, host of Revisionist History and author of 'Outliers' as well as his latest, 'The Bomber Mafia.' Malcolm brings Gladwellian theory to why the re-telling of jokes is never as funny. They riff on evil golf courses, evil search engines, & where that YMCA pool smell might actually come from. Even Malcolm’s mom Joyce makes a cameo. This may just be the tipping point for Working It Out. https://www.yesscholars.org/

Mike is joined this week by Academy Award-winning actor Brie Larson whose films range from Captain Marvel to Room as well as Trainwreck, where her character Kim is married to Mike’s character Tom. Mike bounces jokes off of Brie about people on the internet being angry and vocal about Mike and Brie’s characters being a married couple. The result is hilarious, honest, and ultimately lands on Brie’s joke advice that just might work! In this universe! https://thejewishmuseum.org/buy/donation

Before they became comedians, Mike and Neal both got their start working the door at different comedy clubs. Now, they sit down for a discussion of what it was like for Neal to co-create Chapelle’s Show, and the best advice that Neal received from Chris Rock on his hit Netflix special, “3 Mics.” Plus, new material about protesting yourself, macaroni and a powder intended to represent cheese, and how apologies can feel like a fade-away jump shot. Please allow Mike and Neal to show you to your seats. https://txcivilrights.org/

Mike is a huge admirer of Sarah Silverman and in this episode Sarah brings jokes, stories, and answers to tough questions like, “Why do so many of our comedian friends die young?” Along the way they discuss “coke lyrics,” Sarah’s priceless memory of Joan Rivers, and a story from when Sarah was a kid that is so insane that you actually have to hear it. https://www.kiva.org/

This episode has it all. Bill’s time at SNL. Bill’s time at South Park. Bill’s work at Pixar. Bill’s impression of Mike and Mike’s impression of Bill. Bill’s collaboration with Mulaney and Bill’s discussion of craft in co-creating and writing and acting on the Emmy award-winning HBO hit “Barry.” It’s got jokes. It’s got stories. It even has a moment when Mike forces Bill to compare himself to The Beatles. If that’s not enough, today (June 7) is Bill's birthday. https://www.everytown.org/

This week Mike welcomes Quinta Brunson, the comedian, actor, and writer who blew up from her “He Got Money” memes and viral videos. She has since pivoted into mainstream success as one of the stars of HBO’s “Black Lady Sketch Show” along with roles in “Big Mouth” and as the author of her new book “She Memes Well.” The two discuss the loss of their mutual friend Kevin, the concept of “friend contracts,” and why we fling cats because we love cats. https://mutualaidphilly.com/en/

This week Mike is joined by British comic Nish Kumar and they discuss Brexit, the craft behind building a one person show, and the time Nish was told by a heckler to “go home” when he was pretty close to his home. Nish divulges his lifelong goal to not be Batman or even Robin, but rather the other guy. The sidekick of the sidekick. Find out why Nish should be everyone’s hero. https://helprefugees.org/choose-love/

Mike welcomes his comedy idol and former boss Conan O’Brien whose hit podcast “Conan O’Brien Needs a Friend” prompted Mike to demand that they actually be friends and that Conan come on Mike’s podcast. What results is a magical discussion of Conan’s early political aspirations, why the class clown never becomes a professional clown, and the contagiousness of the Irish accent. https://www.corunummealcenter.org/

In anticipation of this week’s “Worldwide Comedy Pizza Party” Mike welcomes one of the most uniquely funny people alive and the two comics go deep on deep dish. Jo explains her controversial take on eating pizza crust first and builds on Mike’s already over the top “onomatopizza” pun. Along the way Jo tells the story of the time she put on a comedy festival at a carwash at 8 o’clock in the morning and why she ordered 30 pizzas for the audience. Podcast is served. https://www.iamwomankind.org/

These two comedy nerds discuss the elements of math, science, art, and music that go into constructing the perfect joke as they trade collected wisdom about writing from Steve Martin, Mary Karr, Robert Lowell, Philip Roth, and Anne Lamott. They also dig into the rule of 3s, growing up in Massachusetts, the difference between “book smahrt” and “street smaht” and how Gary turned tragedy into comedy in his hit HBO special, “The Great Depresh.” https://donate.hki.org/

Mike and Fred have a candid chat about the secret rules of Portlandia and the comedy writing lessons of SNL. Fred describes how they arrived at the title for “Portlandia” and Mike describes how he arrived at his brand new solo show title that he debuts in this episode. All that and Fred shares his Mike Birbiglia impression, his Ira Glass impression, and explains why a parody of This American Life doesn’t quite work on SNL. https://www.sweetrelief.org/

Aubrey Plaza is a beloved comedic actor for her role as April on Parks & Rec & many acclaimed indie films including "Black Bear" which she not only starred in but also produced. The two discuss their shared love of indie film, Aubrey’s gloriously awkward talk show appearances, & why she'd make the perfect Oscars host. We learn who makes Aubrey laugh, advice she got from Amy Poehler, & how having a stroke at age 19 put her life in perspective. All that plus new pizza jokes! https://hispanicfederation.org/

Mike is joined by Broadway legend Nathan Lane who just so happened to have changed Mike’s life 13 years ago. 1 month after they met Nathan was the witness for Mike’s wedding at City Hall…and then 4 months after *that* Nathan presented Mike’s off-Broadway debut Sleepwalk With Me. Nathan has hilarious stories about working with Matthew Broderick on The Producers and Mike Nichols on The Birdcage as well as insightful notes on the newest material for Mike’s next show. https://broadwaycares.org/

Taylor Tomlinson is only 27 and already has her own hit comedy special on Netflix called “Quarter-life Crisis.” Mike bonds with this prolific joke writer over her unique introduction into comedy when her dad signed the two of them up for a stand-up comedy class at church when she was 16. Mike and Taylor have a candid talk about panic attacks, therapy, and comedians resenting other comedians for the right and wrong reasons. Many jokes. Many laughs. Many confessions. https://www.lafoodbank.org/

Mike welcomes the great Randy and Jason Sklar as they trade jokes about how to say I love you to your parents without sounding like you’re in the Mafia, the difference between outsourcing and ‘Mom-sourcing,’ grandmothers owning sex robots, and what it really means to go skiing with Joe Bags. Listen as these three joke nerds come together and create bits in real time. https://www.youngstorytellers.com/

Prolific, raw, and hilarious comic Nikki Glaser shares childhood memories of her mom in the Slow Round that she’s not yet willing to tell on stage but is willing to say on a podcast. Nikki and Mike both admit that their level of honesty with even their own diaries doesn’t hit 100%. Nikki declares herself the Taylor Swift of comedy and Mike declares himself the Springsteen. This episode is raw and honest and funny. https://www.strayrescue.org/

Yoda. Miss Piggy. The Muppets Take Manhattan. Dirty Rotten Scoundrels. These are just a few entries in the IMDB of Frank Oz. Mike welcomes the show business legend for a candid talk about Frank’s collaborations with Jim Henson and his approach to directing. They also discuss Frank’s new film In & Of Itself, an adaptation of Derek DelGaudio’s brilliant stage show. Also, Frank gives notes on Mike’s new material! It’s candid. It’s frank. It’s Frank. https://www.hfotusa.org/

Keith and Kenny Lucas join Mike for an episode that alternates between utterly serious & supremely silly. They discuss their moving Vulture essay "Our Brother Kaizen," as well as jokes in process about "twin discrimination," and the difference between writing a will and meeting Will Smith. They also discuss the devastating loss of their mutual friend Kevin Barnett and how it led to the Lucas’ sobriety after years being self-described stoners. A must listen. https://ysrp.org/

The award-winning co-creator and star of Crazy Ex-Girlfriend Rachel Bloom joins Mike as the two of them crack into a format never explored in this podcast—the musical! Mike leaves his prepared material behind and pitches a concept for a musical. In turn Rachel pitches Mike her first comedy special—an idea she has never discussed publicly. They also discuss Rachel’s hilarious new book and Rachel delivers some of the best slow round answers of all time. https://feedingamerica.org

A comedy extravaganza featuring Sarah Cooper, Hasan Minhaj, Tig Notaro, Jimmy Kimmel, Maria Bamford, John Mulaney, Ira Glass, Jon Laster, David Sedaris, Pete Holmes, Jon Favreau & Tommy Vietor, Jacqueline Novak, Bowen Yang, & Natasha Lyonne. The perfect episode to share with friends or enemies who haven’t dipped their toes in the Working It Out waters. We are highlighting 6 food banks and Mike is donating 100% of the New Years Eve 6:30 virtual show proceeds to them. https://linktr.ee/WorkingItOutPod

Since Ira Glass was Working It Out’s inaugural guest in June 2020, listeners have frequently requested his return. This week the podcast has its first return guest and its first *second draft*. We also learn what it takes to get a story on “This American Life” and whether Mike’s new story about learning he had cancer at age 19 has what it takes. Ira gives genius notes and spares no feelings. Story nerds, gather round. It’s a must listen. Please consider donating to: https://elpasoansfightinghunger.org/

Mike welcomes the great Natasha Lyonne, co-creator and star of the hit Netflix series Russian Doll. Natasha opens up about her own process as well as the best advice she’s received. Natasha holds Mike’s feet the fire about his new material—so he scraps his prepared jokes for some personal stories he wasn’t planning to tell. This episode is like planning your own funeral, which is also discussed. Don’t miss it. Please consider donating to: https://www.wpaonline.org/ https://www.girlsclub.org/

Mike welcomes award-winning comedian Ramy Youssef. The two friends discuss the unexpectedly controversial elements of his hit series “Ramy.” They also work on jokes about bad wedding speeches, getting kicked in the balls, and the time Ramy told people in Jacksonville that he was Muslim to which a woman replied, “We don’t do that here.” Well, the good news is: we do this here. Enjoy. Please consider donating to: Muslim Anti-Racism Collaborative https://www.muslimarc.org/

Mike is joined by the co-creator and co-star of the comedy classic “Broad City.” They discuss the show’s origins, why we should all hope to “fail flamboyantly,” and why you might quit your job after getting an email from Amy Poehler. Along the way they work out material about why Mike hates magic and Abbi’s crippling fear of running into her ex-girlfriend underwater. On one episode of Broad City Mike and Abbi made out literally. Today on “Working It Out” they make out…with jokes. Please consider donating to: Girls Write Now https://www.girlswritenow.org/

Bowen Yang joins Mike this week for an episode that is as hilarious as it is honest. Listen as Bowen and Mike discuss everything from gay conversion therapy and googling yourself to high school theatre fails and psychedelic shrooms. Bowen and Mike work out standup bits and potential sketches you may be seeing on SNL soon. Plus, find out the one must-have item you’ve been missing your whole life when using a porto-potty. Please consider donating to: Clinton Hill Fort Greene Mutual Aid https://sites.google.com/view/chfgma-org/home

This episode is a little different from the others. If you like it please share it with your college age friend or family member. Also, it’s worth visiting https://votesaveamerica.com/

Jacqueline and Mike have toured together for years and Mike recently produced Jacqueline’s Off-Broadway hit “Get On Your Knees.” On this episode they get nerdy on joke structure: setups, punchlines, tags and secants. They also dig into memories of Jacqueline’s childhood friend getting eaten by a garage door and what “blinking man” means at a crosswalk. Find out why Mike concludes the episode by saying “You must be the first repeat guest!” A must listen. Please consider donating to: Loveland Therapy Fund https://thelovelandfoundation.org/loveland-therapy-fund/

This week Mike welcomes Beth Stelling- the fearless star of the new HBO Max special, Girl Daddy. Beth and Mike discuss their joke nerd instincts and goal to turn pain into comedy. They trade jokes about sex in a rocket ship, middle school burns, flying weenies, and, yes, even dreams about sex with your dad. Please consider donating to: YWCA Dayton, Ohio https://www.ywcadayton.org/how-to-help/donate/