The Springfield Retirement Castle holds a talent show, which the Simpson family attends. Grampa wins the show after performing his version of the song "What's New, Pussycat?". He wins a free autopsy, so the Simpsons visit a funeral salesman to claim the prize. While there, Homer decides to buy a casket and a tombstone for Grampa. He also discovers that a certain kind of tombstone is produced from the same amount of cement as a tennis court, and this gives him the idea to build a tennis court in the family's backyard.
The court is very popular with Springfield's residents, but these residents mock Homer and Marge for losing all the time, thanks to Homer's poor play. Marge pleads with Homer to take the game seriously; however, Homer is too oblivious to how bad he is at tennis. Homer tries to please Marge by entering Krusty's celebrity tournament, the "Krusty Kharity Klassic". Marge, tired of being laughed at, ditches Homer and enters with Bart as her new partner. Homer is outraged that he was abandoned for a ten-year-old boy, and tries to get revenge by entering the tournament with Lisa as his partner, despite Lisa's disapproval.
Because of this, the Simpson family begins to argue and compete against each other. The tournament takes place and in the stands are leading tennis professionals Andre Agassi, Pete Sampras, Venus Williams, and Serena Williams. At the tournament, Homer ditches Lisa for Venus Williams. In response, Marge replaces Bart with Serena Williams as her partner. Ultimately, Serena and Venus replace Marge and Homer with Sampras and Agassi respectively. This forces the family to go back to the bench and resume their normal places in the family; as they enjoy the exhibition of top-class tennis, they agree that it is better to watch things than to do things and Homer offers to buy the family dinner with money he took from Sampras' wallet.