In this special on-location episode, Michelle Obama and Craig Robinson travel to Yellow Springs, Ohio, to sit down with comedy legend Dave Chappelle. Their conversation is hilarious, candid, and wide-ranging, covering Dave’s life, fame, and search for meaning beyond the spotlight. He reflects on his upbringing growing up in Washington, D.C., and Ohio, and how having a foot in each city shaped both his worldview and his comedy. He also shares deeply personal stories about his parents—especially his mother, whom he calls a “greatness whisperer”—and the lessons that gave him the confidence to pursue an unconventional path.