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.

On this episode, host Catie Sheehan takes the show on the road to Casey, Illinois—a town of fewer than 2,500 people that has become home to more record-breaking oversized attractions than any small town has a right to claim.

Recorded on location, Catie explores the streets of Casey and sits down with locals to hear the story behind the Big Things: how they came to be, what they mean to the community, and what the future holds for this one-of-a-kind destination. All 34 of Casey's oversized attractions are free and open to the public, making it one of Illinois's most surprising and accessible stops.

Come for the World’s Largest Rocking Chair. Stay for the community behind it.