After Bart and Lisa find one of his old records, Homer recalls his days as a member of a Beatles-esque barbershop quartet, told via flashbacks.
After Bart starts receiving death threats from his nemesis Sideshow Bob, the Simpsons enter the Witness Relocation Program and move to a "Cape Fear"-esque town several miles away.
After learning that Homer is seriously underqualified for his own job, Mr. Burns enrolls him at Springfield University. While there, he befriends three nerds and accidentally gets them expelled.
Yearning for his lost youth and innocence, Mr. Burns searches for his beloved childhood teddy bear, Bobo. When Maggie comes across the bear, she claims it as her own. Mr. Burns tries to get his Bobo back by any means necessary.
With a Night Gallery style opening, Bart introduces three tales.
The Devil and Homer Simpson
Homer falls asleep, while Carl and Lenny eat all the doughnuts. When he realizes that all the nearest doughnuts are gone, he sells his soul for a doughnut. The devil comes up and signs a contract with him, causing more mischief than Homer thought. His family saves him from an eternity of damnation by a fair trial.
Terror at 5 1/2 Feet
Bart dreams about his death on the schoolbus, and later realizes, that his dream is starting to become real when he is the only one to see a gremlin taking down the bus piece by piece. Nobody sees it except for him, so he tries to get it off.
Bart Simpson's Dracula
Mr. Burns is a vampire and Bart falls victim to his bite, Lisa convinces the rest of the family they must go to his castle and put an end to the curse.
Homer has to cancel his plans with Marge because he got his arms stuck in two vending machines, so Marge goes out with their neighboor Ruth. It turns out, Ruth is somewhat of a wanted criminal. In a Thelma and Louise style story, Marge and Ruth are being chased by Chief Wiggum and Homer. All the while, Lionel Hutz is left to babysit the children.
Homer sees an ad in the paper for a trampoline and he goes to Krusty's and picks it up. The kids love it and he charges the neighbors to use it. When all the children get injured on it, Marge makes him get rid of it. He pushes it off a cliff, a la Wile E. Coyote. Homer and Marge have an argument in which he says that Marge is no fun.
With this realization, she gets very angry and goes to her sisters' house. Patty and Selma show her a self-help video. When Marge starts looking at the self-help information starring Brad Goodman with Homer their relationship improves. They go to a seminar with the kids. Bart acts out while there and the lecturer brings him on stage.
The guru tells the town that Bart is the "inner child" that they should all strive to be. Lisa of course is skeptical, thinking that the guru is just selling easy answers, but the town is buying it. So much so, they hold a "do what you feel" festival. It breaks out into a riot when everybody starts to act irresponsibly and the "be like Bart" era comes to an end. We end with the Simpsons watching the newest episode of "MacArnagle" together.
Bart and Milhouse find which they use to go on a Squishee bender in downtown Springfield. With no memories of what accured, Bart is shocked to find out he joined the Junior Campers. Now a full fledged member, he must attend the father son rafting trip with Homer.
A female employee is hired at the plant. She has an attraction for Homer and Homer must fight his equal attraction for her. In the mean time, Bart becomes an outcast and makes friends with a group of nerds after he is prescribed glasses, scalp salve, special shoes, and throat spray which changes his voice.
During a town meeting, Principal Skinner pitches the idea of opening a casino. Mr. Burns adopts this notion and builds the "Mr. Burns' Casino." Homer takes a job as a blackjack dealer and Marge takes up gambling. At home, Lisa is having difficulties with her school project and Bart opens a treehouse casino.
A cat burglar robs everyone on Evergreen Terrace, including Lisa. Homer gives Lisa a jug to replace her sax. When she is unsatisfied with the jug, he vows to get it back for her. The police are far too incompetent to get anywhere, so Flanders starts a neighborhood watch. Homer becomes the leader and lets the power go to his head. They beat unruly people with sacks of doorknobs and commit other crimes. The burglar steals a jewel from the museum, from under Homer's watch. Abe figures out it was his neighbor, Mulloy. Upon his arrest, Mulloy charms everyone. Homer mocks him in his cell and Mulloy tells everyone that he hid a large sum of money underneath a tree. They all rush to the location and dig for it, finding nothing. Mulloy uses this time to escape from prison.
After Bart sneaks away from a field trip to the box factory, he finds himself working as Krusty's assistant. Krusty lets Bart act out a scene on one of his gags, but Bart messes up the line and says, "I didn't do it." The phrase is an instant success and leads Bart to his fifteen minutes of fame.
Apu loses his job at the Kwik-E-Mart after he sells Homer tanted meat. Homer feels bad and lets Apu live at the Simpson's home while he is unemployed. In an attempt to get his job back, Apu and Homer travel to India to talk with the head of the Kwik-E-Mart corporation. Back in Springfield, James Woods fills in Apu's position.
Grampa realizes that he is no spring chicken and he gives the family their inheritance before he dies. They immediately go to the mall to spend it. Lisa uses her portion to buy a talking Malibu Stacy doll, but when she pulls the string, she is very disappointed in what it says. It spouts nothing but sexist remarks. Lisa goes to complain to the Malibu Stacy company executives, but it doesn't work. She finds out from Mr. Smithers where she can find the creator of Malibu Stacy. She meets with her and together they decide to create a feminist doll: Lisa Lionheart. In the mean time, Grampa decides to recapture his youth, so he gets a job at a fast food restaurant.
At the plant, Homer never gets to be employee of the month; they even choose an inanimate carbon rod over him. At NASA the ratings are down, so they begin a campaign to recruit an everyday loser for the next pointless mission. Naturally, Homer and Barney are among the finalists. The family gets to go to Florida while they train. Barney is kicking Homer's butt, but alcoholism ends his quest. Homer gets really nervous about the mission. He will go with two former astronauts, so he can't screw up like he always does, right? Nope! He brings potato chips into space and wreaks havoc on the mission. James Taylor comes up with a plan to save them, but Homer screws up again. An inanimate carbon rod finally saves them for their reentry. Homer once again fails to get any recognition, because a rod takes the spotlight.
Homer reluctantly goes to a football game with Ned. After Ned shows Homer a good time, they become close friends. Little to Homer's realization, Ned actually starts to have negative feelings toward him.
Bart wins a radio contest which allows him to choose between two prizes: ,000 or an elephant. Bart picks the elephant and names him Stampy. Homer and Marge decide to give the elephant away because he cost to much to feed, so Bart and Stampy run away together.
Mr. Burns watches as Homer cleans the plant as a human chimney sweep. Later Burns nearly drowns in his bathtub when Smithers neglects him. He makes the realization that he has no heir. Smithers would like Burns to consider him, but Burns has other ideas. He announces before a movie that he will hold auditions for his heir. All of Springfield's children show up, but Burns hates all of them. Bart's audition goes terribly when Homer writes down his speech on index cards. (Homer is so dumb in this episode that he cannot even form grammatical sentences.) Bart comes back at night and vandalizes his mansion. Burns is impressed with Bart's destructive side, so he makes him his heir. Burns is still all alone, so Bart agrees to come and stay with him. Burns likes Bart a lot, but Bart thinks Burns is creepy. When Bart returns home, he is bored and he goes back to Burns. Burns tries to trick Bart into thinking that his real family no longer loves him. He does this by hiring famous actors to play his family, but Bart has trouble keeping friends and is lonely. At the plant Burns fires people for kicks and he tries to make Bart fire his father, but Bart proves his loyalty to his family and opens a trap door under Burns.
Superintendent Chalmers fires Principal Skinner after a disaster at the elementary and Skinner re-enlists in the Army. Bart, feeling partially responsible for Skinner's firing, helps to get his old principal his job back.
We begin with Bart and Lisa heading to school. Bart is bored in class, so he forges a note from Marge to cut class and goes to see "Boobarama." Meanwhile, Skinner is trying to track him down after becoming suspicious of the note. Bart narrowly escapes his grasp by stowing away in Quimby's nephew's car. At a Quimby party, the nephew gets in an argument with a waiter. Bart witnesses the waiter clumsily injuring himself. No one else sees it, so the waiter claims Quimby's nephew assaulted him. The trial is a media event, but Bart cannot come forward or Skinner will give him detention. The jury consists of Homer, Skinner, Apu, et cetera. Homer is an incompetant juror and wants to be sequestered at the city's nicest hotel. After watching "MacArnagle," Bart decides to come forward to the Judge. Bart's testimony frees the innocent Quimby, but gets him four months of detention.
It is Maggie's birthday, so the whole family gathers to celebrate. Abe seems especially pathetic and lonely and Marge decides to set him up with her mother, who has the same problem. They hit it off, or so Abe thinks. Bart decides to order a souvenir from "Itchy & Scratchy," so he steals Homer's wallet but the item turns out to be a waste of 0. Abe soon falls in love. He wants to impress Marge's mother by taking her out on the town, but when he does, she falls for Mr. Burns. Abe is heartbroken. When Mr. Burns come over to the Simpsons' house to pick her up for a date we learn that Marge is against her mother's new love interest. Bart gets 0 out of Mr. Burns which he uses to pay Homer back. Mr. Burns asks for his love's hand in marriage, but when the wedding date arrives, Abe breaks up the ceremony. Marge's mother leaves with him, although she is not in love with Abe OR Mr. Burns. We get a loose, yet obvious, homage to "The Graduate", complete with a Simon & Garfunkel parody.
Homer fears he may be a little slow, so he goes to the Adult Education Annex. While there, he decides to teach a class of his own on the secrets of a successful marriage, since that is the only thing he is good at.