Sketch Episodes
179. Bob Odenkirk: The Art of Anger in Comedy
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 ...
176. Jane Wickline & Liva Pierce: SNL, Dukes, and Working Out Songs
This week comedy duo Jane Wickline and Liva Pierce (together known as Dukes) join Mike on the podcast. The three discuss how The Graduate brought Jane and Liva together, their unlikely porn preferences, and what happened when...
172. Nick Kroll Returns: Neil Digression Tyson
This week, Nick Kroll returns to the podcast to discuss the first season of Adults, the last season of Big Mouth and a movie that Mike cannot seem to remember the name of (I Don’t Understand You). Nick and Mike delve into the...
156. Stephen Colbert Returns: A Gift from the Comedy Gods
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 …
150. Michael Ian Black: How to Do Comedy with Your 10 Best Friends
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…
126. Seth Meyers: SNL, Late Night, and a Ton of New Jokes
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. p…
123. Please Don't Destroy: SNL’s Three Sad Virgins
Mike welcomes Ben Marshall, John Higgins, and Martin Herlihy, aka Please Don’t Destroy, known for their wildly popular shorts on SNL. Mike is determined to get Martin to talk more than he did on Pete Holmes’s podcast. The group shares what they like and dislike about each other, and break down what…
119. Rosebud Baker Returns: Pregnant with Jokes and People
Rosebud Baker’s first appearance on Working It Out was in 2021. Since then she’s become a writer on SNL, written for That Damn Michael Che, and become a parent. Now Rosebud returns to talk with Mike about how being a parent affects comedy, and they dispel certain attitudes about filming a comedy sp…
95. Nick Kroll: Old Friends
Nick Kroll and Mike met in college and started doing improv and sketch comedy together. Since then, Nick has become a comedy superstar, from his Comedy Central series Kroll Show, to Oh, Hello, to the animated series Big Mouth and Human Resources, to roles in films like Don’t Worry Darling and the H…
94. Jorma Taccone: The Lonely Island’s Comedy Revolution
Mike and Jorma Taccone are old friends and former next door neighbors. Jorma also just so happens to be an acclaimed screenwriter, director, actor, and member of the legendary comedy team “The Lonely Island” with Andy Samberg and Akiva Schaffer. The Lonely Island made the Saturday Night Live classi…
84. Chloe Fineman: The SNL Star Who Can Literally Do Anything
Chloe Fineman’s first TV appearance was doing bird calls on Letterman. Now she plays a multitude of beloved characters on SNL and a role in Noah Baumbach’s forthcoming film White Noise. Mike and Chloe discuss how she got noticed with her celebrity impressions on Instagram and what happens when you …
66. David Cross: Fully Committed Dad
This week Mike welcomes David Cross, who is a legend in comedy and also makes cameos in Mike’s dreams. The two comics discuss the origins of Mr. Show, why Tobias from Arrested Development is so different from David himself, and how sometimes it’s hard to be an optimistic dad when the reality in fro…
57. Stephen Colbert: Laughter As An Act Of Love
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 pa…
49. Keegan-Michael Key: Schmigadon't Think Twice
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 s…
22. Abbi Jacobson: The Broad City Makeout Party
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 a…
21. Bowen Yang: How Do You Write a Sketch For SNL?
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 ma…