Episode - 7F16
First Aired - 2/21/1991
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.
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- Comically Missing the Point: Homer met a guy who looks like Dr. Hibbert and told about a lost twin and he fails to notice a connection. Also, he had to be outright told his half-brother lives in Detroit.
- After Homer told Herb that they're brothers, he's in shock. But Homer thought he lost the connection.
- Downer Ending: 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 "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).
- 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.)
- Identical Twins: The head of Shelbyville Orphanage looks like Dr. Hibbert and said he has a lost twin.
- Mean Boss: Herb is extremely dismissive and temperamental to his employees, viewing them as privileged idiots (in stark contrast to his own upbringing). 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.
- Never My Fault: Herb blames Homer for ruining his company despite putting him in charge, shelving all other projects and outright ignoring his employees' warnings.
- Riches To Rags: Herb thanks to Homer.
- Self-Made Man: Herb.
- Special Guest: Danny DeVito as Herb Powell
- Title Drop: 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.)