155. David Sedaris Returns: A Creative’s Dream and a Fact Checker’s Nightmare

Rachel Feinstein Returns: She's on Fire(Recorded June 2024) Working It Out hall-of-famer Rachel Feinstein returns to the podcast on the heels of her hit Netflix special Big Guy. Rachel explains why her firefighter husband loves being roasted in her special and why he pronounces the word “cash” like “quiche.” Rachel shares an absurd road story featuring Kevin Hart and Keith Robinson and discusses why you should never ask a comic how *they* felt about their show. Plus, new material about God getting sober, normalizing spa days, and Rachel attempting to cuddle with a boyfriend at the scariest hotel she’s ever stayed at.Please consider donating to Friends of Firefighters and The Billy Moon Foundation

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 plays F**k, Marry, Kill, with his own published works and Mike can’t accept the answer. Please consider giving money to a stranger in need.

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 down his own performance in the new film The Best Christmas Pageant Ever.Please consider donating to Homebody Industries

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 and ice crushing machines are symbols of wealth.Please consider donating to Girls Inc.

(Recorded March 2024) 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?Please consider donating to Sanctuary For Families

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 five-year-old Maria wanted to be called "Blueberry.”Please Consider Donating To: Downtown Women's Center Los Angeles

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, moving from work friends to friend friends. Plus, jokes about soccer game injuries and the pitfalls of lecturing your spouse on pop culture.Please consider donating to Hellen Keller International 

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 the ups and downs of a creative life, including the reasoning behind the cancellation of a novel she wrote that took place in Russia. Plus, some bawdy jokes and stories care of Liz’s uncles and grandfather, and the surprising reason why Liz was stopped at airport security. Please consider donating to The Loveland Foundation

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

 In the 90s, Michael Ian Black’s college sketch group The State got a show on MTV, spawned another iconic group, Stella, and led to the classic movie Wet Hot American Summer. Now Michael sits down with Mike to talk about how all 11 members of The State have remained friends through the ups and downs of show business. Michael shares his advice on how to keep a comedy group together as well as a marriage, as he and his wife just celebrated 26 years. Plus, jokes and stories about truth or dare, the pros and cons of leaving New York City, and behind the scenes of Michael’s love scene with Bradley Cooper.Please consider donating to the Mark Twain Library.