Marge is fed up with Homer's antics and leaves, especially after he allows Fat Tony to use the Simpson house for some adult filming to cover a gambling debt. While out on her own, Marge comes across a dashing marine biologist.
Lisa must confront her fear and learn how to sleep again when a cemetary moves in next door and disrupts her sleep.
Milhouse tries to break his parents apart again upon realizing that he had it better when they weren't together. When Maggie catches chicken pox, Homer decides it would be a good idea for the parents of Springfield if all the kids in town to catch it and throws a party to that end.
"Bartificial Intelligence" When Bart goes into a deep coma, the Simpsons family takes on a robot replacement. "Survival of the Fattest" Homer takes part in a variation of "The Most Dangerous Game". "I've Grown a Costume on Your Face" Homer taunts a witch and all the Springfield residents are forced to take on the character of their Halloween costumes.
Bart puts in time with lonely Marge and starts to earn the taunt of "mama's boy".
Homer’s inability to embrace Lisa’s Father’s Day book the same way he does Bart’s Father’s Day Toolman causes Lisa to develop DDD (Disappointed Daughter Disorder).
Homer's fight with a bunny referee at a children's egg hunt ruins Marge's social opportunity. Lisa tries to learn to speak Italian. Marge joins a female society and finds they have plans to rob Mr. Burns.
Homer is sent to pick up Mr. Burns' new Italian sports car in Italy after Burns wrecks his old car. While the Simpsons are in Italy, they have a car accident and discover that Sideshow Bob is the mayor of a local village. When Lisa inadvertently reveals Bob's identity to his unaware wife and child, Bob decides to resort to his old killing ways once more and tries to eliminate her.
The Christmas themed Simpsons stories including “The First (Annoyed Grunt) – El,” when Homer describes the birth of Jesus, "I Saw Grampa Cussing Santa Claus," when, during World War Two, Grampa accidentally shoots down Santa Claus and "The Nutcracker... Sweet" where Springfield hops to the familiar tune of the "Nutcracker".
Homer comes to doubt Abe as his real father after some decades old mail gets delivered.
Homer and Marge decide to send Bart off to a behavior improvement camp after he steals the key to the school's steam tunnels and destroys the school.
The Simpsons family welcomes in Groundskeeper Willy when Bart destroys his current home. Lisa takes the opportunity to make him more civilized. Homer tries to find a replacement pair of blue pants.
The Simpsons take a trip through "Carl's Caverns," which ends up being a harrowing experience as the family falls through the floor of the cave and Homer gets wedged into the ceiling. While Bart and Marge try to find some help, Lisa decides to tell Homer a treasure story about a rabid sheep in Mr. Burns' mansion which comes after her and Burns.
Homer tries to edge out Flanders in a rubber duck-racing contest at a church fundraiser, but Flanders wins and trades his prize to Marge for some babysitting duties with Rod and Todd. Meanwhile, Homer, Bart and Lisa get into a hairy situation at a farm for former celebrity animals.
Homer becomes obsessed with Lenny's new plasma screen television and desperately wants one of his own. When Marge enters them into a contest for a plasma screen TV, they end up winning a tour of the Fox Television studios and decide to have Marge appear on a wife-swapping reality show in order to win their plasma TV money.
Grandpa manages to screw up the town’s attempts to land an NFL team by attacking the NFL commissioner during a state of confusion. Abe finds a new lease on life, however, when he ends up taking up bullfighting at the town stadium which would have been used for football.
Homer becomes the nuclear power plant employee trainer when the work is outsourced to India, but soon is obsessed with his own power. Meanwhile, Patty and Selma kidnap Richard Dean Anderson, only he ends up wanting to stay and the ladies realize they can't get rid of him.
As the family waits for their food, they pass the time by telling stories. Lisa tells about the Mayflower’s journey to America, where Marge and her kids are Pilgrims and they are joined by a knave named Homer who joins their family to escape the authorities.
The family attends the "Itchy and Scratchy Musical." The musical's director is a graduate of Springfield Elementary and Principal Skinner puts his foot in his mouth when he makes sexist comments about her education and that of women in general.
Marge goes on a cleaning frenzy before the housekeeper she’s won the services off comes to the house. One spot remains and she mixes a number of toxic cleaners together to tackle the job.
Working through their checklists of things to do before summer ends, Lisa gets the family to go a museum. At the Springfield Museum of Natural History there is an exhibit Lisa is excited to see on Women’s History turns into an exhibit on the history of weapons, which excites Homer and Bart.
When Homer hears that the Isotopes are on a winning streak, he takes the family to the game. The first baseman’s game is going bad, caused by his sexy singing wife Tabitha embarrassing him during the game’s national anthem.