After Lisa's new pet guinea pig destroys the Simpsons' living room art, Marge falls in love with a beautiful painting at the Van Houten's yard sale, which Homer snaps up for 20 bucks. But, when Lisa reveals it's by a famous early 20th century painter and could be worth $100,000, Marge and Homer face a dilemma: split the money with the Van Houtens, or keep the cash as a "cushion" for their kids.

Marge is concerned that Lisa is dating below her station when she brings home competitive eater-in-training Lucas Bortner, and she enlists Homer to help Lisa explore other options. Meanwhile, Bart is thrilled to receive free gifts from Snake Jailbird after he helps the convict escape from a jam, but when a betrayal from Milhouse puts Snake back in jail, Bart must forge a plan to set him free.