211: Laura Krafft

Laura Kraft is a comedic writer and actress, an iO Chicago and Second City alum and former staff writer for the Colbert Report. Jimmy talks to her about how improv helps her write for television, how she seems to find herself in the right place at the right time, and lessons she’s learned from her dad.

208: Micah Philbrook

Micah Philbrook is one of Chicago’s most thoughtful and innovative improvisers and teachers.  He teaches at The Second City Training Center, he’s a founder of pH Productions, and he performs in the Tim and Micah Project.  Jimmy sat down to talk to him about joining a cult-like improv group when he first moved to Chicago, the importance of hanging out in the improv community, and what he likes most about improv.

202: Joe Bill

Joe Bill is an international improv teacher and performer. He is a co-founder of the Annoyance Theater and tours with Mark Sutton in Bassprov. He has taught at Second City, The Annoyance and iO Chicago and continues to teach around the world. Jimmy sat down with him in this live episode to talk about The Annoyance, the day he quit stand-up, and his unique psychological approach to improv.

199: Matt Dwyer

Matt Dwyer is a writer, stand-up and podcaster. He was one of the youngest people to be hired for the Second City Touring Company at the age of 21. He has written for Funny or Die and Jonah Ray’s Hidden America on Netflix. We talked to him about hanging out at Second City when he was high school, how getting fired at Second City led him to stand up, and the importance of writing for improvisers.

197: Peter Grosz

Peter Grosz is best known as one of the two guys in the Sonic commercials, but he has also written for The Colbert Report and Late Night with Seth Meyers. He has performed at The Second City etc., the UCB, Boom Chicago, and iO Chicago. Jimmy talks to him about why he still loves improvising, getting hired to write for Colbert and why he likes to play the unlikable Sidney Purcell in HBO’s VEEP.

184: Tim Kazurinsky

Tim Kazurinsky is an actor who was on Saturday Night Live from 1980-84 and is best remembered as Carl Sweetchuck in the Police Academy films. He is also a screenwriter who co-wrote About Last Night. Jimmy sat down with Tim to talk about why he started taking improv classes at The Second City, how he got on SNL and making his Broadway debut last year in An Act of God with Jim Parsons.

175: The Defiant Thomas Brothers

The Defiant Thomas Brothers (Paul Thomas and Seth Thomas) is a brilliant two-person sketch group out of Chicago. After splitting up 9 years ago, they have gotten back together and now have an open run at The Second City Training Center. Jimmy sat down with The Defiant Thomas Brothers at this year’s Chicago’s Skectchfest and talked to them about getting back together, how audiences have changed, and race in comedy. You are going to love this episode!

174: Mick Napier

Mick Napier is the founder and artistic director of the acclaimed Annoyance Theater in Chicago, an artistic consultant at Second City and the author of the new book, Behind The Scenes: Improvising Long Form. Jimmy sat down with him to talk about some of the concepts in the book such as giving yourself permission to be funny, how to appeal to a non-improv audience and how to get in the right frame of mind when improvising.

166: Mike O’Brien

Mike O’Brien has been a writer and featured player on Saturday Night Live. He is an alumni of The Second City Main Stage in Chicago and was a member of the legendary Harold team The Reckoning at iO Chicago. Jimmy sat down and talked to Mike about his love for uncomfortable comedy, his journey from writer to performer on SNL, and his new comedy album, Tasty Radio.

164: Anne Libera

Anne Libera is the director of The Comedy Studies program of Columbia College at The Second City in Chicago. She is a well-respected teacher and director who was the Executive Artistic Director of The Second City Training Center for eight years. Jimmy sat down and talked to Anne Libera about going from actor to director, becoming friends with Stephen Colbert at Northwestern University and the importance of working with people you like.


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