Andy St. Clair, a longtime favorite of the Chicago improv community, sits down with Jimmy and talks about coming up at iO Chicago, his time on The Second City's main stage and his television and commercial work.

Edgar Blackmon, star of The Second City Chicago's main stage, joins Jimmy for a lively discussion of race and comedy, overcoming personal tragedies, and why an actor can shit on someone's face as long as it's funny. Then Edgar joins Jimmy for some very therapeutic improv.

Lucas Neff, one of the stars of FOX's Raising Hope, sits down with Jimmy to discuss his rambunctious youth, becoming an actor by mistake, and discovering his passion for improvisation. Enjoy!

Holly Laurent, veteran of the Second City Mainstage, sits down with Jimmy and discusses her religious upbringing, coming into her own as an improviser and her time at The Second City.

John Lutz, former actor on 30 Rock and SNL writer, joins Jimmy for a personal conversation about his upbringing, getting started in improv, and why Donald Trump was the worst SNL host.

Dan Harmon, creator of NBC’s “Community” and host of the podcast Harmontown, sits down with Jimmy to discuss the frustrations of the creative process of producing a sitcom and self sabotage.

Andy Richter, longtime sidekick to Conan O'Brien, joins Jimmy at iO West for a completely candid interview and a wonderful improv set. Don't miss Andy explain how he came to be hired by Late Night, his evolution as an actor, and the true identity of Paul Swanson. Enjoy.

Matt Besser, a founding member of the Upright Citizens Brigade, hosts Jimmy at the UCB Theater LA. Matt bears all for Jimmy, discussing his time in Chicago, the founding of UCB, the recent controversy over paying performers, and even a relationship that was previously unknown to the audience. Matt could not have been a better guest. Improv lovers should NOT miss this episode.

Before moving to Los Angeles in 2012, Amanda Blake Davis was a favorite of the Chicago improv scene. She starred in revues at The Second City Chicago, earning a JEFF Award for that work, and could regularly be seen at iO and The Annoyance Theater. Amanda joined Jimmy for a candid interview and a wonderful improvised scene.

Steve Waltien from The Second City mainstage joins Jimmy for a frank conversation about overcoming anxiety, how the death of his father informed his work, and the shelf life of a good shirt. Then, Steve and Jimmy find themselves in a bunker with ominous consequences.