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.

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.

After that, Catie sits down with Brandy Nance, a double-duty wine insider who knows the terroir as well as anyone. Brandy is both Marketing and Event Director at Blue Sky Vineyard in Makanda and the Executive Director of the Shawnee Hills Wine Trail, and she serves up all sorts of useful insights about wine tasting in this up-and-coming region.

Great food, fantastic wine, epic outdoor adventures—Southern Illinois is the real deal.