Colt Cabana is an internationally known professional wrestler and host of the super popular podcast The Art of Wrestling. Jimmy talks to Colt about his improv and comedy back ground, the comparison between wrestling and improv, and the importance of promoting yourself.

Mike O'Brien has been a writer and featured player on Saturday Night Live. He is an alumni of The Second City Main Stage in Chicago and was a member of the legendary Harold team The Reckoning at iO Chicago. Jimmy sat down and talked to Mike about his love for uncomfortable comedy, his journey from writer to performer on SNL, and his new comedy album, Tasty Radio.

Mike Carr has been the Artistic Director at SAK Comedy Lab in Orlando, FL, since 2006. He has performed with Mission Improvable, studied at iO Chicago where he was on the Harold team Revolver and gotten to improvise at his job at The Monster Inc. Laugh Floor at Disney World. In this episode, Jimmy talks to Mike at the Tampa Improv Festival about how he got started in theater and what it is like to be an artistic director at an improv theater.

Anne Libera is the director of The Comedy Studies program of Columbia College at The Second City in Chicago. She is a well-respected teacher and director who was the Executive Artistic Director of The Second City Training Center for eight years.

TJ Jagodowski and Dave Pasquesi are true improv legends. Their show, TJ and Dave, is an international award-winning show that has inspired improvisers all over the world.

Anthony LeBlanc is an actor, teacher and director who recently directed the current Second City etc. show "Soul Brother, Where Art Thou?" He was also a cast member of the Second Mainstage, where he put up two revues. Jimmy talks to him about how the death of his brother has inspired him, why his dream job was to work for NASA and his insight about race in comedy today.

Jen Ellison is a director, writer, teacher and performer who is best known for directing The Second City e.t.c.'s 38th revue, "Apes of Wrath."She teaches at The Second City, DePaul University, and Columbia College. In this episode, Jimmy talks to Jen about discovering a passion for directing at a young age, the transition from DePaul's Theatre School to ComedySportz, and the importance of admitting your mistakes.

Irene Marquette is a performer, teacher, writer and director. Best known for the host of the popular "Curio Show" she teaches at iO-Chicago, The Annoyance and Comedy Studies at Columbia College. She also regulary improvises with Tone and Super Human at IO-Chicago. Jimmy talked to her about starting out doing murder mystery dinner theater with her parents, finding improv at 19 in a coffee shop in Las Vegas and how important it is do the improv you love doing.

Joel Murray joins Jimmy during a recent trip to Chicago and talks about his time with The Second City Chicago, his career in film and television, and growing up with brothers Bill Murray and Brian Doyle Murray.

Jimmy explores the process of getting rejected in comedy with guests Abbi Jacobson and Ilana Glazer from Broad City, David Koechner, Dan Harmon, Colbert writer Brian Stack, and more.