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Kelly Leonard: Improv Comedy at The Second City

The Science of Creativity

Release Date: 08/19/2025

Kelly Leonard: Improv Comedy at The Second City show art Kelly Leonard: Improv Comedy at The Second City

The Science of Creativity

Kelly Leonard has been involved with improv comedy for almost 40 years. He's worked with actors and comedians including Stephen Colbert, Tina Fey, Keegan Michael Key, Seth Meyers and Amy Poehler. He started working at the Second City Theater in Chicago in 1988, eventually becoming producer in 1992, and later, taking on roles and titles including Executive Director, Executive Vice President, and Creative Adviser. Since 2016, he’s been Vice President of Creative Strategy, Innovation, and Business Development. He’s produced hundreds of original revues. His 2015 book Yes, And received rave...

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Dr. Jonathan Feinstein, a professor at Yale University, studies the developmental paths of creative individuals, including entrepreneurs, inventors, artists and scientists. His book Creativity in Large-Scale Contexts was published in 2023. He is also the author of The Nature of Creative Development (2006). His current work focuses on models of creative engagement, centering on guidance, learning, opportunities, and paths of development. What do we choose to learn and explore as we develop our creative interests and passions? What opportunities arise, which projects do we pursue? His approach...

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Everyone who works in television and movie comedy knows Charna Halpern. She’s trained thousands of actors, writers, and producers at her Chicago theater, founded in 1981, called the iO theater. In this episode, Charna tells personal and funny stories about actors from Chris Farley and Neil Flynn to Tina Fey and Amy Poehler. Along with actor and director Del Close, Charna invented modern improvisational theater in the 1980s. The art form known as long form improvisation—a 20 or 30-minute fully improvised one-act play—was developed at the iO theater, and is still found on their stage at...

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Kelly Leonard has been involved with improv comedy for almost 40 years. He's worked with actors and comedians including Stephen Colbert, Tina Fey, Keegan Michael Key, Seth Meyers and Amy Poehler. He started working at the Second City Theater in Chicago in 1988, eventually becoming producer in 1992, and later, taking on roles and titles including Executive Director, Executive Vice President, and Creative Adviser. Since 2016, he’s been Vice President of Creative Strategy, Innovation, and Business Development. He’s produced hundreds of original revues. His 2015 book Yes, And received rave reviews in Vanity Fair and the Washington Post. He co-leads a new partnership with Booth School at the University of Chicago that studies behavioral science through the lens of improvisation. He is a popular speaker, appearing at Aspen Ideas Festival, Chicago Ideas Week and TEDxBroadway and hosts the Second City Works/WGN Podcast “Getting to Yes, And.” 

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Music by license from SoundStripe:

  • "Uptown Lovers Instrumental" by AFTERNOONZ
  • "Miss Missy" by AFTERNOONZ
  • "What's the Big Deal" by Ryan Saranich

Copyright (c) 2025 Keith Sawyer