Chicago Comedy: Second City, First Laughs

Chicago Comedy: Second City, First Laughs

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.

Haunted Illinois: The Stories Locals Swear Are True

On this episode, host Catie Sheehan ventures into the supernatural side of Illinois, summoning up secrets about the state’s most haunted places—from Alton and Decatur to Springfield, Chicago, and Galena. First, Catie sits down with Troy Taylor, a prolific author of more than 150 books on the paranormal, a podcaster, and a pioneer of the ghost tour movement. Troy got his start as a kid, guided through the darker corners of Decatur by his Irish immigrant great-grandfather. He shares some of Illinois' most spine-tingling tales—including the legend of Resurrection Mary, the vanishing hitchhiker of Archer Avenue who has interacted with multiple people over the years. After that, Catie drills down on Galena with Ted Williams, co-owner of the Haunted Galena Tour Company. A city of just 3,000 people that draws nearly a million visitors a year, Galena's 1850s-era streetscapes are the perfect setting for things that go bump in the night. Ted talks about some of his favorite phantoms, including the mysterious Lady in Black and a ghost cat said to curl up on the beds of the historic Dowling House.

Go Big: Larger-Than-Life Landmarks

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.

Illinois Made Me: Andy Richter

In this episode of the Enjoy Illinois: Let's Go! podcast, host Catie Sheehan sits down with comedian, actor, and podcaster Andy Richter for a wide-ranging conversation about the state where he grew up—and how the Land of Lincoln shaped him. Best known as Conan O'Brien's sidekick and as a breakout fan favorite on Season 34 of Dancing with the Stars, Richter is more than a late-night legend—he's a proud son of Illinois who grew up in Yorkville, spent formative years on the Chicago comedy scene, and carries the Midwest with him everywhere he goes. From his training days at Improv Olympic and The Annoyance Theatre to his many roles on the small screen, Richter reflects on what Illinois gave him. He also offers some fantastic recommendations via the Land of Lincoln Lightning Round.

Illinois' Route 66 Hidden Gems

On this special episode, host Catie Sheehan celebrates the Route 66 Centennial with two guests who know the Mother Road inside and out. The show opens with a word from Governor JB Pritzker on what this milestone year means for Illinois. First up is Amanda Bryden, Registrar of History at the Illinois State Museum in Springfield. Bryden co-led "Miles of Memories," the Route 66 Oral History Project, a remarkable collection of 100 video-recorded interviews with the people who lived, worked, and traveled the road during the pre-interstate era. She shares stories from the archive, including a striking account of what travel looked like for Black families navigating segregation-era Route 66, and offers her picks for must-see stops along Illinois' stretch of the highway. Next, Sheehan sits down with Josh Waldmire, third-generation owner of the Cozy Dog Drive In in Springfield. Waldmire shares the full story behind his grandfather Ed's invention of the Cozy Dog in the 1940s, what keeps the restaurant feeling like a trip back in time, and what's on the horizon for the centennial year, including a Major League Eating contest at the Mother Road Festival this September.