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December 18, 2019
Happy 60th Birthday, Second City!

The Second City in Chicago turned 60 this week. Though I was never on the Main Stage or even in the touring company, Second City has always had a special place in my heart. I taught at the training center, worked in the business theater and have done plenty of shows there. And the best part […]

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October 17, 2016
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 […]

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September 26, 2016
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 […]

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August 15, 2016
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 […]

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July 24, 2016
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 […]

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July 11, 2016
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, […]

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April 11, 2016
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 […]

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February 9, 2016
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 […]

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February 2, 2016
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 […]

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December 8, 2015
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 […]

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