Oh Brother, Where Art Thou?

Danny DeVito as Herb Powell

"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, 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.

The episode was written by Jeff Martin and directed by Wes Archer. American actor Danny DeVito provided the voice of Herb. The episode features cultural references to cars such as the Edsel, the Tucker Torpedo, the Ford Mustang, and the Lamborghini Cheetah. Since airing, the episode has received mostly positive reviews from television critics. It acquired a Nielsen rating of 15.4, and was the highest-rated show on the Fox network the week it aired. Some fans were upset with the sad ending of the episode, and as a result the producers decided to write a sequel, "Brother, Can You Spare Two Dimes?", in which Herb regains his fortune and forgives Homer.

After watching the latest McBain film, Grampa suffers a mild heart attack. Thinking he might die, he is prompted to confess a long-hidden secret: Homer has a half-brother. Grampa explains that he met a carnival prostitute before marrying Homer's mother, and they had a son that they left at the Shelbyville Orphanage. Determined to find his brother, Homer and his family go to the orphanage and find out that Grampa's love child was adopted by a Mr. and Mrs. Powell and named Herbert.