Episode - 7F16\\
First Aired - 2/21/1991

''Oh Brother Where Art Thou'' is the 15th episode of the second season of ''WesternAnimation/TheSimpsons''.

After suffering a heart attack at the movie theater, Grampa realizes his mortality and lets Homer in on a dark family secret: Homer has a half-brother named Herb (the product of a one-night stand Grampa had with a dunk-tank carny-cum-prostitute) that he gave up for adoption before Grampa married Mona. When Homer finally finds Herb's whereabouts, the Simpsons are off to Detroit, where Herb recruits Homer to create a car for his company.

See the [[YMMV/TheSimpsonsS2E15OhBrotherWhereArtThou YMMV]] page for details.
* AreWeThereYet: Bart and Lisa annoy Homer with that question during the car ride to Detroit.
* {{Bowdlerization}}: Bart singing the word "bastard" after justifying his use of it was edited out when shown on UK TV.
* BreadEggsBreadedEggs: For their day out, Bart wants to go on a boat ride, and Lisa wants to go on a pony ride. Cut to Lisa riding a pony on Herb's yacht.
* CharlieChaplinShoutOut: One of the beggars in Herb's vicinity is Creator/CharlieChaplin.
* ComicallyMissingThePoint: The man in charge of the orphanage who Homer meets looks like Dr. Hibbert and tells Homer about his own lost twin brother. Homer fails to notice a connection. He also fails to get the enormous repeated hints at where his brother is and has to be directly told he is in Detroit.
** After Homer told Herb that they're brothers, he's in shock. But Homer thought he lost the connection.
* DownerEnding: Homer is left heartbroken after a bankrupt Herb disowns him. Some fans were so upset by Herb's downfall that the producers would ultimately do [[Recap/TheSimpsonsS3E24BrotherCanYouSpareTwoDimes "Brother, Can You Spare Two Dimes"]] to give Herb a happy ending again (though a much later episode ["Changing of the Guardian"] reveals that Herb went broke again, and viewers don't get any information as to what happened).
** Though the commentary also reveals the original ending had Herb coming up with another idea as the bus pulled away.
* EpicFail: The '''$82,000''' [[note]](equivalent to over $140,000 today)[[/note]] monstrosity Homer designed.
* {{Flashback}}: A quick one explaining how Abe had Herb. Quickly followed by Abe marrying Mona and the birth of Homer. (Incidentally, this is the first time Mona ever appeared.)
* GoneHorriblyRight: Desperate to save his company, Herb turned to Homer to design a car. He got a big, ridiculous, unwieldy machine whose production bankrupted him on the spot.
* IdenticalTwins: The head of Shelbyville Orphanage looks like Dr. Hibbert and said he has a [[LongLostRelative lost twin]].
* JapanTakesOverTheWorld: Powell Motors is losing ground to the Japanese. When Herb loses his fortune, his company is bought by a Japanese company.
* MeanBoss: Herb is extremely dismissive and temperamental to his employees, viewing them as privileged idiots (in stark contrast to [[SelfMadeMan his own upbringing]]). [[HoistByHisOwnPetard This ends up his own undoing]], as he refuses to take their warnings of Homer's incompetence seriously, and forces them to continue with his doomed project until it's too late. They apparently know not to give what people want.
* NeverMyFault: Herb blames Homer for ruining his company despite putting him in charge, shelving all other projects and outright ignoring his employees' warnings, who despite being 'privileged idiots' as he put it still know enough about business to be on the board of a car company.
* NoCelebritiesWereHarmed: UsefulNotes/ThePope is apparently also present during the presentation of the new car.
* NoKillLikeOverkill: In the [=McBain=] movie, [=McBain=] throws the villain out a window, landing on an oil tanker that ''[[MadeOfExplodium explodes]]''
* RevealShot: Herb asked Homer and his family to visit him. We pull back to see his huge mansion.
* RichesToRags: Herb thanks to Homer.
* RightHandVersusLeftHand: The failure of Homer's project, what isn't caused by Homer's horrible conceptions, is exacerbated by this. Any attempts to halt the project or warn Herb of the damage Homer is causing [[PoorCommunicationKills fall on deaf ears]], either due to [[NotNowKiddo Herb's dismissive attitude towards his employees]], or [[InsufferableGenius their pompous and demeaning method of explanation]].
* SelfMadeMan: Herb.
* SpecialGuest: Creator/DannyDeVito as Herb Powell
* TitleDrop: Homer when he goes to the Shelbyville orphanage and thinks it's been replaced with a gas station. (Then he learns it just moved across the street.)