Film critic Jay Sherman is among the judges at the Springfield Film Festival, which Mr. Burns conspires to win by bribing some judges.

The family is on a nature walk through “Carl’s Dad Caverns,” when Homer tries to get a piece from a stalactite. This results in the family falling through the cave floor and winds up with Homer getting stuck in the ceiling of one of the lower chambers of the cave. Marge, Bart and Maggie go off to find help, while Lisa stays behind and tells her father a story to pass the time. Her story involves running from a bighorn sheep and into Mr. Burn’s mansion. The pair evades the tenacious sheep by finding refuge in the mansion’s attic, where Mr. Burns tells her the story of how he came to work at Moe’s Tavern by losing a scavenger hunt with a rich Texan. While there he learned (and tells to Lisa) the tale of the Moe’s treasure. The stories within stories culminate in the fate of the treasure being determined in the cave.

Homer is bamboozled by Army recruiters and winds up in basic training, where he runs afoul of a tough-minded colonel and is assigned to play the enemy in war games.

Selma and Patti's home movies make Marge nostalgic for the Barnacle Bay vacations of her youth, so Homer takes the family there, but the area has changed since the Bouviers were little girls.

The Simpsons' pooch, Santa's Little Helper, becomes a police dog.

The series' 18th Halloween show features three vignettes that parody movies: one that spoofs "Mr. & Mrs. Smith"; one that sends up "E.T."; and one that parodies "Se7en."

Marge opens a gym for real women because she's disenchanted with Springfield's snooty, glitzy L.A. Body Works. Her gym, Shapes: A Gym for Women, is a huge success, launching a chain that makes Marge rich and famous. But Homer fears Marge will leave him for someone more attractive and goes to extreme lengths to try to save his marriage.

Homer and Marge remember the ups and downs of their marriage through a series of flashbacks, including the time they each began flirting with guests at a glamorous party - a situation that led to a food fight and an unexpected swim in the pool.

When the adjustable rate on the Simpson couple's mortgage resets at more than the pair can afford, they must sell their house. Good Samaritan Ned Flanders buys the house and rents it out to them at an affordable rate. But Homer pushes his luck too far when he takes advantage of Ned's generous landlord duties.

When Marge learns Springfield Elementary is the worst school in the state, she and Homer rent an apartment in the upscale Waverly Hills school district so Bart and Lisa can attend a better school. Meanwhile, Homer moves into the rented Waverly Hills apartment and gets used to the bachelor lifestyle.

Krusty grudgingly adds a pretty, singing cohost named Princess Penelope to his show in order to attract more female viewers. Girls love her, and ratings improve, but Bart and Milhouse want to get the show back to the way it was. The situation gets more complicated when Krusty and Penelope fall in love and decide to get married. Meanwhile, Homer, Lenny, and Carl consider working at a competing nuclear plant when Mr. Burns cuts off their daily doughnut service.

Homer is completing his court-ordered community service when he befriends his supervisor, Chief Wiggum, by offering him one of his sandwiches. Touched by the act of kindness, Wiggum assigns the other convicts unpleasant tasks, but allows Homer to join him at the picnic table. They continue to grow close, but when the Chief gets injured during a botched bank robbery, Homer doesn't come through when Wiggum needs him the most. Meanwhile, Bart becomes addicted to Battle Ball, a Japanese game made up of plastic balls and magnetic cards, and his family and teachers try to help him kick the habit.

Bart and Homer make a film based on Bart's comic book character Angry Dad. The cartoon becomes a critical favorite and begins to win a number of awards, but Bart becomes upset when Homer takes all of the credit during acceptance speeches.

Lisa discovers her new best friend is a Republican who is opposing her in the class election.

When Marge tries Homer's new high-tech glasses on, he learns she's seeing a marriage counselor; Bart refuses to buy Nelson a Valentine's Day card.

The Planet Express crew come to present-day Springfield to prevent the Simpsons from destroying the future.