When Rev. Lovejoy disciplines Bart for a prank he pulled in church - he tricked the organist into playing Iron Butterfly's ""In-A-Gadda-Da-Vida" - he and co-conspirator Milhouse begin arguing over whether man really has a soul. Bart scoffs at the notion and agrees to "sell" his soul (a piece of paper with the words "Bart Simpson's Soul") to Milhouse for $5. A series of situations makes Bart realize maybe he really did sell his soul, prompting him to go all-out to get it back from Milhouse, who isn't willing to sell. Meanwhile, Moe attempts to open a family-style ...
First, a freak lightning storm causes giant advertising mascots to come to life. Next, Groundskeeper Willie dies and swears revenge on the kids in their dreams. Finally, Homer accidentally finds himself trapped in another dimension.
Mr. Burns institutes a new calisthenics program at work. Most employees enjoy the morning workout, except Homer, who is too lazy. He finds out that if he goes in disability, he will be exempt from the exercises. He finds hyper-obesity among the list of disability, so he gorges himself on food to balloon up to 300 pounds.
To get out of cleaning a part as community service, Homer fakes his own death. When this results in the family's utilities being cut off, Marge puts pressure on him to reveal that he is alive. However, the spurious news of his "death" brings his long-lost mother - a hippie who is on the run from the law because of her activism against Mr. Burns - back to Springfield.
To avoid politics, former President George Bush and his wife Barbara retire to Springfield, citing its low voter turnout. They quickly become friends to the conservative Flanders family, but George soon becomes the enemy of Bart and Homer Simpson.
After Grandpa destroys their television set, the Simpsons go to an outlet mall to buy a new one. Marge decides to peruse a clothing store, and buys a discounted Chanel suit. A chance encounter with a High School acquaintance, while wearing the suit, leads to an invitation to join a country club. Marge becomes obsessed with pleasing the club's upper-class clientèle to so she can be accepted.
Bart gets a check he wanted signed by Krusty back stamped. As Krusty was supposed to autograph it, Bart wants it taken back to sign, but inadvertently reveals Krusty as a tax fraud. Krusty's lifestyle is stripped down to that of an average citizen, his show ruined and most of his possessions sold in an auction. Bart is mad at himself, particularly after a sobbing Krusty commits suicide by piloting his plane, the I'm-Onna-Rolla-Gay, into a mountainside. Bart sees visions of Krusty everywhere, but are they illusions or real life?
Washed-up movie star Troy McClure is pulled over for driving without corrective lenses, and forced to go to the DMV to get his eyes checked. While there, he meets Selma, who he asks out for dinner. Spotted by a reporter, he quickly realizes that being seen in public with a woman will grab enough headlines to revitalize his career, leading to a whirlwind romance between him and Selma.
Unable to get out of a mis-scheduled spring vacation, Principal Skinner makes up the holiday "Go to Work with Your Parents Day," giving Lisa the chance to spend time with Homer, and Bart the chance to work with Patty & Selma at the DMV. When Bart makes his own fake driver's license and Martin wins a bundle at the stock market, Bart rents a car, and takes Milhouse, Martin, and Nelson Muntz on a huge road trip.
Grandpa Simpson reveals to Bart that he and Montgomery Burns were part of a World War 2 unit known as the Flying Hellfish, which stole priceless art from a German castle during the war, of which the last surviving member would inherit the fortune. When another member of his platoon dies, Abe and Burns remain the last two survivors, and Burns vows to make sure Grandpa doesn't become the last Hellfish, until Abe and Bart vow to find the fortune before Burns does.
Depressed about his inability to keep up with the existing music scene when Bart reveals how uncool his interest in 1970's rock music truly is, Homer decides to take Bart and Lisa to the Hullabalooza music festival to show them this isn't the case. Failing at that, he nearly sparks a riot and gets shot at with a cannon(ironically for Peter Frampton) which bounces a fake pig off his fat belly, and ends up being hired as part of the festival's freak show, touring with bands such as Smashing Pumpkins, Cypress Hill, Sonic Youth, and yes, Frampton.
The end of the school year, and an empty yearbook causes Lisa to contemplate her lack of popularity. When Ned Flanders is summoned for jury duty and offers Homer a chance to stay at his beach house, Lisa sees this as the opportunity to reinvent herself as a slacker in the hope of gaining friends, which proves to be far more successful than she could possibly imagine --- but not if Bart has any say in the matter.