Growing up poor in a St. Louis African American community, Dick Gregory (b. 1932) gained his improvisational skills trading insults on neighborhood streets. He honed his ironic barbs in Chicago’s black nightclubs before crossing over to mainstream venues. His success at the Playboy Club led to bookings at nightspots around the country, network television exposure, and a recording contract. His first book, From the Back of the Bus, offered satiric observations on race in America in the midst of the civil rights era.