The family is greeted by folk singer Ewell Freestone when they visit a peach farm, but when Marge goes overboard with peach-inspired dishes, Lisa and Bart try to get rid of the unwanted fruit. Later, Lisa becomes a magician's apprentice to the legendary Great Raymondo who helps her develop her craft, but a schoolgirl crush clouds her judgment when she is coaxed into revealing the Great Raymondo's most famous magic trick to his phony archnemesis. But when the rival magician's act takes a risky turn, the Great Raymondo has one last trick up his sleeve and stages showdown with Ricky Jay, Penn & Teller and David Copperfield , showing them why he is the master of the craft.

Lisa makes a new friend at school - Harper, who happens to be super-rich, while Homer makes friends with Harper's dad and sets out to continue living the good life when Lisa decides to end the friendship.