High Quality Content by WIKIPEDIA articles! "Oh Brother, Where Art Thou?" is the fifteenth episode of The Simpsons` second season. It originally aired on the Fox network in the United States on February 21, 1991. In the episode, Grampa confesses that Homer has a half-brother, whom Homer immediately tries to track down. He eventually discovers that his brother is Herbert Powell, the head of a car manufacturer. Herb immediately starts to bond with Bart and Lisa, and he invites Homer to design his own car. Homer`s car design turns out to be a disaster, which causes Herb to become bankrupt.