When Lisa writes a letter to the International Olympic Committee, they decide that Springfield will be home to the next Olympics. To honor the Olympics, there is a contest for the games' mascot. Homer creates a mascot for the Olympic Games named Springy, the Springfield Spring, which becomes the mascot (much to Patty and Selma's dismay, who created a mascot named Ciggy the Cigarette) and everyone in Springfield prepares for the games. When the IOC inspects the town, things go well until Bart does a stand-up comedy routine that insults foreign nations, which only Principal Skinner, Homer, and the children find funny. In response, the IOC decides not to let Springfield have the Olympics anymore (they award it to Shelbyville, who presumably and chronologically lost it to Sydney), and Superintendent Chalmers blames Skinner for putting Bart on stage with his racy jokes. Skinner initially keeps his case strong by telling Chalmers that the comedy worked well during rehearsal, but to prevent losing his job, he makes every one of the school's students do 20 hours of community service. After sending Milhouse to collect medical waste on the beach and leaving Martin to start a basketball program between inter-city gangs, Skinner has Bart assigned to work at the Springfield Retirement Castle, where Lisa also works voluntarily. Bart is dismayed at how little the seniors are allowed to do.
Meanwhile, Homer gets 1,000 springs he intended to sell as Olympic mascots. He uses various get-rich-quick schemes to sell off the mascots, but fails miserably due to Springfield's hatred of Bart's comedy routine. Ultimately, he is forced to flush the mascots down the toilet. At the time Lisa leads the seniors in "imagination time", but when she departs, Bart makes the seniors escape to get a taste of freedom. Bart takes the seniors on a trip on the town and on a boat ride, and Lisa is initially shocked to see these things happen, but nevertheless, she is quite impressed by what Bart does for the seniors, though the seniors eventually tell Bart that they don't mind their quiet, mundane life back at the home. Suddenly, their boat crashes into Mr. Burns's schooner that cleaves the cruise ship in half. The boat begins to sink, and an attempted rescue by Jack LaLanne fails. The seniors turn on Bart, but Grampa defends him, saying Bart gave them the best fun they have had in years. However, the ship mysteriously rises back to the surface, which is revealed to be because of the springs Homer has flushed down the toilet, which have formed a small pile just underneath where the boat is, causing the boat to bob up at the surface long enough for the Coast Guard to rescue everyone. Bart finishes his community service time, but decides to help the seniors still enjoy themselves.