John Mulaney: He's Funny and Here's Why
(Recorded January 2026) For the 200th episode of Working It Out, Mike sits down with one of his oldest friends and one of the podcast’s first ever guests, John Mulaney. The two discuss monkeys wearing space suits, old stories from the road, and how John’s career changed after having kids. They work…
219. Michelle Buteau: From TV News to Her Own TV Series
Michelle Buteau was a local TV news editor in New York until she tried stand-up for the first time, only days after 9/11. Since then she’s become an international touring comedian, bestselling author, and co-creator and star of her own Netflix series Survival of the Thickest. Now Michelle talks wit…
Fred Armisen: Is He Joking?
(Recorded August 2025) Having recently toured together with John Mulaney, 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…
217. Aaron Chen: High Quality Jokes from a Low Capacity Kind of Guy
Comedian Aaron Chen may be known internationally for his role on the hit Australian TV series Fisk, but he’s been a working stand-up since the age of 15. In fact, he might be the only Working It Out guest who learned to drive commuting to and from comedy clubs with their dad. Now he’s got a hit Net…
216. Wanda Sykes: Mike's Dream Guest
Wanda Sykes is one of Mike’s original dream guests for the podcast. Now, on the heels of her new Netflix special, Legacy, Wanda talks with Mike about how they both started in DC, and why Wanda left her job at the NSA to pursue a career in stand-up comedy. Wanda tells the story of how she moved from…
214. Robby Hoffman: It's a New Dawn
This week Mike and Robby Hoffman sit down for their first in-depth conversation like, as Robby puts it, two cats cautiously getting to know each other. Mike and Robby work out new jokes about vending machines and AI, share advice about marriage, and Robby begs Mike’s fans to stop sending him emails…
Jenny Slate: Unafraid of Sadness
(Recorded October 2025) 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 nake…
Advice for New-ish Comedians (with Gary Simons and Listener Questions)
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 st…
111. Gary Simons: A New Comedian Asks Mike 10 Key Questions About Starting Out in Comedy
25 years ago, Mike won Georgetown University‘s funniest person on campus contest. This week's guest Gary Simons won it three years ago. Now, Gary has been opening for Mike’s new tour and has a lot of questions: How do I get an agent? How do I go from doing 5 minutes to doing an hour? Any relationsh…
Trump Winces During Military Ceremony | Karl-Anthony Towns, Sienna Miller, Stefano Domenicali, Gary Simons | Thursday, September 24
Jimmy addresses the latest news, like President Trump greeting Chinese President Xi Jinping for his visit to Washington D.C., before speaking with Karl-Anthony Towns, Sienna Miller and Stefano Domenicali and welcoming comedian Gary Simons for stand-up.
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