It is really hot and the Simpson family does not have air conditioning. They try to live in a tent beside the refrigerator, but that does not work. Otto drives by with a traveling swimming pool. This gives Bart and Lisa the idea to hound Homer for a pool which they relentlessly do until he caves in and buys them one. All the kids in the neighborhood come by to use it. Bart tries to jump from his tree house into the pool, but winds up breaking his leg. He will have to spend the rest of the summer in a cast, so there will be no more swimming for him. He watches as Lisa becomes incredibly popular. Bart finds himself a new hobby by spying on the neighborhood with Lisa's telescope. While looking out the "Rear Window" of the house, Bart thinks he's seen Flanders commit a hug. He gets Lisa to break into Flanders' house and look for clues. He watches as Flanders returns home with an axe. He goes to help her, broken leg and all. Then Flanders tells them that Maude has been away at bible camp, but now she is back.
Lisa wants to practice her saxophone because she is auditioning for first chair in the school band. A new student named Allison enters her class. Allison was skipped ahead a grade by Principal Skinner. Lisa is really jealous of her and is horrified to learn that Allison is going for first chair saxophone, too. Meanwhile, Homer and Bart find an overturned truck full of sugar. Homer fills up his car with it. Lisa loses her quest for first chair and Allison becomes the new smart girl at school, making Lisa feel terrible. When Lisa tries to befriend her, it does not work. Bart helps her think of a way to beat Allison at an upcoming diorama contest. Homer guards his sugar pile in the backyard and he is completely paranoid about an Englishman trying to steal it to put it into his tea. Instead bees find his stash. Beekeepers come to get them back. When it rains, Homer's sugar pile melts into the ground. Bart and Lisa manage to sabotage Allison's project, but Lisa can't go through with it. Neither of them wins the contest anyway; first place goes to Ralph Wiggum. The three smart kids, Lisa, Allison, and Ralph, walk home together.
Through a series of clips from past episodes, the family recounts their trials and tribulations with love.
The Simpson family takes a vacation to Itchy & Scratchy Land. When the robotic Itchys and Scratchys go haywire, the Simpsons must find a way to escape the island.
Homer has been listening to a conservative radio talk show host. One day Sideshow Bob calls in from prison, voicing his conservative views. The host, Barlow, gets Sideshow Bob released from prison. Upon Sideshow Bob's release, the town's Republicans want him to run for mayor against Quimby. Bob outwits Quimby in every debate and wins by a huge landslide. Lisa is skeptical (as usual) about how he did it, so she investigates. Meanwhile, Homer has problems with the gang from Riverdale. Sideshow Bob imposes a few new policies. For one he condemns the Simpsons' house to help make way for the new Matlock Expressway, much to the delight of the seniors. Second, he gets Bart placed in kindergarten. Lisa discovers how Sideshow Bob won the election: he had dead people vote for him. He admits to all of this when Bart and Lisa outwit him in front of the town. Sideshow Bob goes back to prison.
The family becomes caretakers of an estate in the mountains owned by Mr. Burns, where he cuts the cable and takes out all beer, which leads Homer to insanity.
Time and Punishment
Homer fixes the toaster and it becomes a time machine. While visiting the past, he kills a bug, which affects the future in a big way. When he tries to fix the timeline, he breaks it again. He ends up trying numerous times until he settles on his family eating with frog-like tongues.
Principal Skinner finds a solution to his overcrowding problem and the quality of meat in the cafeteria: eating the students.
The parents stop the kids in the middle of their game and bring them to church. Bart sees Lovejoy's daughter, Jessica and it's love at first sight for him. He tries to impress her, even by trying to become a good person, but nothing is working. So he goes back to being the devil's cabana boy and pulls a prank on Willie. This is what impresses Jessica, so she invites him over for dinner. The Lovejoys do not like him, especially after talking about last night's episode of Martin. This makes Jessica like him even more. They hang out together and behave badly, but she pretends not to know him in public. Jessica is using him, but he will do anything to please her, but it begins to depress him. He vows to quit seeing her, but he just can't help himself. Of Jessica and Bart, he is the lesser of two evils, especially when Jessica pins the blame on him after she steals the church's collection plate. The congregation chases him and Jessica won't come forward; it's up to Lisa to tell everyone that it was Jessica that stole the plate. The plate is found in Jessica's room, Jessica continues on making men do whatever she wants.
Lisa is failing gym. To make up the grade, she joins a pee-wee hockey league. Soon, her team must face off against Bart's, putting them in direct competition.
Homer and Marge attend a candy convention and have to find a babysitter for the kids. After the convention, Homer gives the babysitter a ride home. He notices that there is a very rare gummy stuck to her bottom, so he reaches out and grabs it. Homer is accused of sexual harassment and the whole town is against him until Willie saves the day.
Homer and Marge are having a troublesome sex life until Grampa introduces Homer to a home remedy love tonic. They soon go on the road together, trying to make some money off Grampa's potion. All the while, all the adults in Springfield are taking advantage of their new love lives, leaving the children thinking that UFO's are to blame.
The family discovers Marge's fear of flying after they try to go on vacation with Homer's free airline tickets. On Lisa's advice, Marge visits a psychiatrist to get down to the bottom of her seemingly unexplainable fear.
Homer has trouble with a plumber and at work he begins noticing that Lenny and Carl have a lot of mysterious privileges at work. Lenny keeps giving hints that they are part of a secret. Homer follows them one night when they go to their secret meeting place. Every male in Springfield that he knows is in the place. Lenny lets it slip that they are the Stonecutters and Homer wants to be a member. He discovers that Abe is a member, which means that he can easily become a member. They initiate him with painful rituals and he is member #908. As a Stonecutter, the plumber quickly fixes the leak in his basement and he gets a new parking space at work. When they celebrate a big occasion Homer desecrates a sacred parchment. As his punishment Homer is kicked out of the club and they take his clothes. Upon stripping him, they discover a birthmark. It is shaped like their logo, which means he must be the chosen one. They begin to worship him. They let him win at card games. Soon his life becomes meaningless and too easy. Lisa recommends that he begin helping people in the community using his new authority. The Stonecutters don't like helping people, so they form a new secret society, the "No Homers". As the only Stonecutter left, he begins feeling lonely. Marge makes him realize that he is part of a more exclusive club... the Simpson family.
The family gathers together as Homer tells the story of why there are no pictures of Maggie in the house.
Principal Skinner releases a weather balloon, but Bart turns it into an anti-Skinner prank. Principal Skinner is upset, so Bart's punishment is to help him log amateur astronomy sky coordinates. Bart gets up at 4:30 AM to assist Skinner. When Skinner steps away, Bart discovers a comet. The nerds of the school, super friends, soon embrace him. When they figure out that his comet is approaching Springfield and will annihilate the town, Professor Frink comes up with a plan to intercept the comet with a missile. Unfortunately the missile misses and destroys the only bridge out of town; the people of Springfield are doomed! The Flanders family let the Simpsons in their bomb shelter. The rest of the town asks Ned if they can come in as well. When the shelter is too full, one person has to leave, so they kick Ned Flanders out. Soon they feel guilty about it, so they all leave to die with him. The comet comes through the atmosphere and breaks apart due to all of Springfield's polluted clouds.
After spotting a billboard for clown college, Homer cannot resist and upon becoming an official Krusty the Clown impersonator Homer runs into some trouble with the mob.
A prank call from Bart to Australia results in a 0 dollar phone bill. When Bart refuses to pay the charges, Australia indicts him for fraud and the family takes a trip to the land down under so Bart can apologize for his shenanigans.
Homer loses all his money in pumpkin stocks and must turn to Patty and Selma for a loan. He tries his best to keep it a secret from Marge. Meanwhile, Bart is late for physical education class sign-ups and has to take a ballet class.
Springfield is the least popular town in America. They have a town meeting on how to attract tourists and Marge pitches the idea for a film festival. After they accept her idea, she searches for a film critic to be the judge and Jay Sherman is her choice. He comes to Springfield and stays with the Simpson family. Mr. Burns decides to enter the festival to boost his reputation, and makes a horribly self-indulgent film. Jay Sherman fits right in with the Simpson family, but he and Homer quickly form a rivalry. After the screenings, Homer has already made up his mind he is going to vote for the dumbest video, the one by Hans Moleman. This is an injustice to Barney's film about alcoholism, which is the best of the bunch. The jury includes Jay, Homer, Krusty, Marge, and Mayor Quimby. Mr. Burns bribes Krusty and Quimby to vote for him. Homer decides to change his vote to Barney's film, so Mr. Burns loses. What does Barney win? Why beer, of course! Mr. Burns later tries (unsuccessfully) to bribe the Academy Awards.
When Lisa gets lost at a Renaissance Faire, she meets a mysterious fortune teller offers to tell her about her future by reading her cards. We flash forward to 2010 at an Eastern university where she meets an arrogant proper young English gentleman named Hugh. They fall madly in love with each other, and Hugh proposes to Lisa. Lisa brings Hugh to Springfield so that he can meet the Simpson family. Hugh spends time with Bart and Homer, and it turns out to be a nightmare. On the day of the wedding, Hugh suggests that they go back to England and leave her family out of her life. Realizing that she has fallen in love with the wrong man, Lisa gives the engagement ring back to Hugh, and the wedding is called off. The fortune teller then vanishes in a puff of smoke and Lisa meets back up with Homer, appreciating him a little more than usual.
The family notices that Santa's Little Helper has been destroying the house. He soon runs away and goes back to the dog track from which he came. He finds another greyhound there and humps her in front of everyone. The family decides to bring her home. The two dogs quickly fall in love. Santa's Little Helper's bitch has 25 puppies, but 25 puppies are too much for the Simpson family. They spoil an important dinner party. The family decides to give them away, but Mr. Burns dognaps them. They wonder what he could possibly want with them. Bart and Lisa go to spy on him and see what he is doing. He plans to hug them and make them into a greyhound skin tuxedo. They try to save the puppies, but Mr. Burns catches them before they escape. Mr. Burns has one of his characteristic changes of heart and decides not to hug them. He keeps all the puppies which grow to become successful racing dogs, making him even richer.
Bart pushes the teachers to strike. Local Springfieldians take over the teaching positions, so Bart must find a way to fix things between the teachers and Principal Skinner.
Bart gets his appendix removed after swalling a jagged metal prize in his bowl of Krusy-O's. He is awarded 0. Meanwhile, "Bleeding Gums" Murphy passes away and leaves Lisa his saxaphone. To honor Murphy, Lisa must raise 0 to buy his record so that it can be played on the radio.
Marge has a very dangerous encounter with a criminal. The adrenaline rush inspires her to become a police officer.
The children of Springfield wage war on Shelbyville, after their beloved town lemon tree comes up missing. The fathers of Springfield take Ned's RV to search for their boys.
The entire town of Springfield is enraged at Mr. Burns after he steals oil from the school, destroys the retirement home, closes down businesses and plans to block out the sun. After the town meeting, Mr. Burns is found shot. Who was the gunman?