When Bart fails to turn in his homework, Mrs. Krabappel sends a letter home about Bart’s behavior. Despite Bart’s best efforts to intercept it, Homer reads the letter, and he and Marge visit Principal Skinner for a parent-teacher conference. Furious, Homer punishes him, but Marge takes a more sympathetic approach. When Bart realizes he can pit Homer and Marge against each other to his benefit, his scheming reaches new heights.
When Miss Hoover asks her students to research their family history, Lisa is horrified to discover that most of her ancestors were bad people – a motley crew of horse thieves and deadbeats. But while rummaging through the attic, Lisa happens upon a diary kept by her ancestor, Eliza Simpson. As Eliza’s story unfolds, Lisa learns that her family was part of the Underground Railroad, a group that helped slaves escape to freedom. Eliza recounts liberating a slave named Virgil, but when Lisa presents her findings at school, some of her classmates refute it, leaving Lisa determined to exonerate her family’s name.
Homer takes Marge out for a romantic evening of ice skating and hand-holding, but upon entering the rink, they encounter a curling team practicing. Marge and Homer take to the ice and discover their love for the sport, and soon after, join the curling team and compete with them in the Olympic trials. Team Springfield claims the win and moves on to the 2010 Vancouver Games where Bob Costas covers the action. Meanwhile, sleazy vendors introduce Lisa to the world of collecting Olympic pins, and before long, Lisa is hopelessly addicted.
Homer blows off Marge to buy a lottery ticket and winds up winning the million-dollar jackpot. Fearing how Marge will react if she finds out the reason Homer missed their date, Homer keeps his newly inherited fortune a secret and spoils his family with “anonymous” gifts. When Bart finds out, he and Homer spend the money like it’s going out of style, including buying front-row to tickets to see Coldplay in concert.
Filmmaker Morgan Spurlock travels the country interviewing fans of the animated series; Spurlock visits the home of the show's biggest fan and the organization at the center of the biggest Simpsons controversies. Academy Award-nominated filmmaker Morgan Spurlock documents 20 years of Our Favorite Family.
Milhouse and Bart try to help Krusty regain his popularity after he is forced to restructure the format of his TV show.
Grandpa becomes famous when a human-interest columnist publishes his anecdote about serving on a battleship in World War II that was struck by a torpedo. Guest Mitch Albom provides his own voice.
When all the power goes out during a blizzard in Springfield, Bart observes the bonding moments between Lisa and Maggie, and he starts wanting a brother himself.
Lisa decides to walk through the field after getting lost in a game of hide-and-seek, but she discovers three teenage girls who are practicing Wiccans instead. Although Lisa doesn't believe in their spells, the girls convince Lisa into understanding that they never hurt anyone and they ask her to join. However, Chief Wiggum arrives before Lisa is inducted, and Lisa becomes the star witness in the case of the three girls' arrests. Meanwhile, after discovering that they make moonshine, Homer begins hanging out with Cleatus and his hillbilly friends.
Principal Skinner is getting fed up with Bart's pranks, so he informs Bart that he is not the best prankster after all. A former student named Andy Hamilton is hailed as the best prankster, and Bart sets out on a mission to track Andy down. However, when Bart finds out that Andy is a 19-year-old still in his pranking days, they become fast friends.