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 ...
Determined to avoid a work exercise program, Homer intentionally gains weight in order to qualify for disability and work from home. However, he soon realizes that being morbidly obese comes with its own problems.
After buying a Chanel suit at a bargain price, Marge finds herself invited to a country club by a former schoolmate. Taken in by the opulence of the place, she is soon overcome by a desperation to fit in.
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?
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.
Another member of Grampa Simpson's WWII platoon dies, leaving only him and Mr. Burns. Years earlier, the men stole a number of priceless masterpieces from Nazi Germany, and now Mr. Burns aims to ensure he is the one to inherit them.