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.
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.