EPISODE · Jun 22, 2026 · 34 MIN
Chicago Comedy: Second City, First Laughs
from Enjoy Illinois: Let's Go! · host Illinois Office of Tourism
On this episode, host Catie Sheehan heads to Chicago — the city that invented modern improv and has been exporting comedic innovation to the world ever since.First, Catie sits down with Kelly Leonard, who spent more than 30 years at The Second City, rising from dishwasher to executive producer. Over the years he hired Steve Carell, Stephen Colbert, Tina Fey, Amy Poehler, Keegan-Michael Key, and many others who would go on to define American comedy. Kelly reflects on what makes Chicago such a singular comedy incubator and shares some favorite haunts, including the Old Town Ale House, Jazz Showcase, and The Golden Apple Grille and Breakfast House.After that, Catie connects with Jennifer Estlin, owner and executive producer of the Annoyance Theater, the Lakeview institution that has been a creative home to Jane Lynch, Andy Richter, Aidy Bryant, and Matt Walsh, among others. Jennifer explains how the Annoyance fits into Chicago's comedy ecosystem alongside Second City and iO, and why visitors can still catch lightning in a bottle there on any given night.
What this episode covers
On this episode, host Catie Sheehan heads to Chicago — the city that invented modern improv and has been exporting comedic innovation to the world ever since.First, Catie sits down with Kelly Leonard, who spent more than 30 years at The Second City, rising from dishwasher to executive producer. Over the years he hired Steve Carell, Stephen Colbert, Tina Fey, Amy Poehler, Keegan-Michael Key, and many others who would go on to define American comedy. Kelly reflects on what makes Chicago such a singular comedy incubator and shares some favorite haunts, including the Old Town Ale House, Jazz Showcase, and The Golden Apple Grille and Breakfast House.After that, Catie connects with Jennifer Estlin, owner and executive producer of the Annoyance Theater, the Lakeview institution that has been a creative home to Jane Lynch, Andy Richter, Aidy Bryant, and Matt Walsh, among others. Jennifer explains how the Annoyance fits into Chicago's comedy ecosystem alongside Second City and iO, and why visitors can still catch lightning in a bottle there on any given night.
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Chicago Comedy: Second City, First Laughs
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