Old Money is the seventeenth episode of Season 2. It aired on March 28, 1991. It was written by Jay Kogen and Wallace Wolodarsky and was directed by David Silverman. Audrey Meadows guest starred as Beatrice Simmons, Grampa's new girlfriend. Professor Frink makes his debut in the episode. The episode features references to films such as If I Had a Million, and the Star Wars and Batman film franchises. This is the only episode to date, not counting The Simpsons Movie, to actually show which characters are voiced by which voice actors.
Grandpa Simpson falls in love with Beatrice Simmons, a fellow resident of the Springfield Retirement Castle. During the course of their brief romance, Bea passes away and leaves Grandpa her entire savings, $106,000. Grandpa formulates to give the money to charity but he can't choose which one is worthiest, but when he is unable to make the the perceptive choice, Grampa heads for a casino to gamble it away.
In a month's time, Grandpa plans to present Beatrice with a present on her birthday. However, Homer comes for their monthly outing with Grampa, explaing that he can't go, as it is his girlfriend's birthday. Homer thinks this is just Grampa acting cranky and not wanting to come along. Grampa ends up being dragged along with the family to Discount Lion Safari. At the refuge, the family's car becomes stuck in the mud and, to make matters worse, hungry lions begin circling the car, trapping the family in the car overnight. After a hunter helps run the lions off the next morning, Grampa returns home expecting to see Bea. However, Homer pulls up just in time for an ambulance to pull away. It turns out that Bea had died of a burst ventricle when he was out with the family.
Grampa is saddened by these events, but mentions that Bea must have cared for him, in that she didn't request that he be a pallbearer at her funeral. Homer tries to explain how sorry he is, but Grampa is too angry to listen. Blaming Homer for making him miss the final precious moments of Bea's life, he vows not to forgive Homer and disowns him as a son.
After returning to the retirement home, Grampa is visited by Lionel Hutz, the executor of Bea's estate. It turns out that Bea was a wealthy widow, and left an inheritance of $106,000 to Grampa. Bea's stipulations say that Grampa can enjoy this money any way he sees fit. He tries everything from buying a fez (which is claimed to have belonged to Napoleon), to going to an amusement park, but none of these alternatives make him happy. While on the rollercoaster at the park, Bea appears to Grampa in the form of a ghost, telling him that if the money isn't helping him, it should go to those who it could benefit.
Also at Bea's request, Grampa goes to visit Homer and his family. At dinner, Grampa announces his intentions to give Bea's money away. He plans to have people come talk to him, and then he will choose who is in most need of it. This announcement soon gains local media attention, and a line forms for people to make requests of Grampa for the remaining money (even reporter Kent Brockman reports on this, then gets in line).
After a number of interviews, Grampa still hasn't made up his mind. At a suggestion by Jasper, he goes on a senior citizen gambling trip, with the possibility that he could double or triple the remaining funds. When Homer finds out about this, he races to stop Grampa, and succeeds when Grampa almost loses the money in a game of roulette. This gesture causes Grampa to forgive Homer.
Outside the casino, Homer asks Grampa if he has figured out yet what to do with his inheritance. Looking at his hands, Grampa explains that he has. With the inheritance, Grampa helps renovate the retirement home, and has the dining room named in Bea's honor.