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.

!!This episode contains examples of:
* AreWeThereYet: Bart and Lisa annoy Homer with that question during the car ride to Detroit. Marge tells them they'll turn around if they don't stop, Homer complains that he wants to see his brother, an annoyed Marge tells him it was an idle threat.
* BlatantLies: When Herb disowns Homer at the end, Marge tries to comfort him by saying "I'm sure he said it to make conversation".
* {{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.
* BrickJoke: Herb tells the family that his personal cook will make anything they want any time of day, leading Homer to ask hypothetical questions about making pork chops even at 4 a.m. After some family bonding scenes, we cut to Homer in the middle of the night and calling the cook.
* 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. Homer thought he lost the connection.
* CoolUncle: Herb consistently spoils his nephew and nieces. He'd even rather be called "Unky Herb" since "Uncle Herb" sounds so formal.
* 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).
* EpicFail: Herb asks Homer to help his company design a car for the "average American man". Homer instead designs an '''$82,000''' HummerDinger that gets Herb laughed straight into bankruptcy. Herb didn't really make things easy on himself by 1) believing '''Homer''', with his immense stupidity, could actually represent an "average American" and 2) Herb decided not to listen when the rest of the research team tried to warn him.
* {{Flashback}}: A quick one explaining how Abe had Herb. Quickly followed by Abe marrying Mona and the birth of Homer. Also, Mona makes Abe swore to never mention anything about Herb so Homer would grow up respecting his father, which Abe has forgotten about. (Incidentally, this is the first time Mona ever appeared.)
* {{Foreshadowing}}: A cop who pulled the family car over was suddenly nice to Homer. Later, a guy in the bathroom is confused by his appearance. It turns out to be because Herb looks like Homer.
* 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.
* HereditaryCurse: Lisa observes that Herb was a big success, until he learned he was a Simpson.
* HummerDinger: The "Homer". Everything about its design flies past AwesomeButImpractical and straight into the ridiculous, and the price makes it only available to rich people.
* IdenticalTwins: The head of Shelbyville Orphanage looks like Dr. Hibbert and said he has a [[LongLostRelative lost twin]].
* IHaveNoSon: Or in Herb's case, "I Have No Brother" It took the next season for Herb to forgive Homer.
* InsufferableGenius: Herb's design team. They might have been taken seriously if they hadn't been so pompous or explained everything in a demeaning, "we-know-what's-good-for-you" attitude, such telling Homer "Americans don't want [X]" whenever he asked for something. The lead designer quickly calling Herb to complain and (from the context) making personal insults towards Homer didn't help.
* ImprobablyCoolCar: Averted. "The Homer" is a car only [[FatIdiot Homer Simpson]] would deem "cool" in any way, shape or form, [[EpicFail and it (and its absurd price tag) become the laughing stock of the motor industry]] and sinks Herb's company.
* {{Irony}}: The Car Built for Homer, which was supposed to appeal to the average consumer, came with an absurdly high price tag.
* JapanTakesOverTheWorld: Powell Motors is losing ground to the Japanese. When Herb loses his fortune, his company is bought by a Japanese company.
* JerkassHasAPoint: The design team makes some valid points about fuel efficiency and automobile designs, but how they express them ultimately demeans everything.
* LoopholeAbuse: Bart delights in being able to use the word "bastard" since that's technically the correct way to describe Herb.
* MeanBoss: Herb is extremely dismissive and temperamental to his employees, viewing them as privileged idiots (in stark contrast to his own upbringing). This ends up being 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]]''.
* PetTheDog: Bart telling Homer that he actually thought his car was cool.
* RememberedTooLate: During the flashback, after Homer was born, Abe promises his wife not to tell Homer about the carnival incident. We then transition back to reality, where Abe, having just told everything to Homer, exclaims, "Whoops! Forget what I just told you."
* 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 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. It's established he put himself through business school and built his company from the ground up.
* SkywardScream: Homer during the TitleDrop.
* 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.)
* UncannyFamilyResemblance: The only differences between the two brothers are that Homer's fatter and Herb still has his hair; otherwise, exactly alike. They lampshade it when they first meet.