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George thinks he has a heart attack, but really just needs a tonsillectomy. Kramer recommends George see a holistic healer instead, who gives him a tea that makes George sick.
George quits his job and immediately regrets it and tries to return to work as if nothing happened. Jerry is convinced money he had hidden in his laundry bag went missing at the laundromat.
After discovering an old picture she painted of Ringo Starr, Marge takes an art class. Marge is eventually hired to paint Mr. Burns but portrays him as naked and frail.
Jerry inherits some of his grandfather's stuff and in the collection is a statue that looks like one that George's family had until he broke it. Jerry promises it to George, but the statue gets stolen.
When Elaine is depressed about her apartment, Jerry overhears an opening in his building and immediately tells Elaine. Meanwhile, George tries wearing a wedding ring to meet women.
Grampa falls for an old woman, Beatrice Simmons and when he goes to celebrate her birthday, Homer drags him away. Bea ends up dying that night, and Grampa blames Homer for costing him their final moments together.
When Santa's Little Helper destroys everything in the house, Homer sends him to obedience school. Just when the dog is about to fail out of obedience school, he bonds with Bart and passes.
Grampa tells Homer he has a half-brother, who he tracks down. He learns his brother is Herbert Powell (Danny DeVito), the head of a car manufacturer in Detroit. Herbert lets Homer design his own car which bankrupts the company.
Selma begs Marge to help her find a husband. When Bart gets in trouble, Homer has to talk to Principal Skinner who he decides to set up with Selma, only he falls for Patty instead.
George gets angry when his girlfriend, Carol, doesn't return his calls and leaves nasty voicemail messages. When he learns she's on vacation, he and Jerry break into her apartment to clear the machine.