Matt returns from a run of shows at his former improv theater and saw a weird movie on the plane, friend of the show Lawrence O'Donnell Jr. made the headlines with his self-described greatest accomplishment, and Penn recaps a night of great jazz and takes a deep dive into the all-natural pest...

Piff The Magic Dragon fills in for Matt Donnelly. Piff has returned from an alternate reality to celebrate his new U.S. citizenship, brainstorm a brand new show for his upcoming tour, and try and convince Penn that he is in fact The Luckiest Dragon Alive.