Bart’s betrayal of Lisa leaves him having to deal with the guilt. Meanwhile, Homer proves to be a chess savant, leaving the Springfield citizenry in awe.
Fast-food restaurants in Springfield turn healthy, leaving Homer to turn to a greasy spoon for comfort (food), and childhood memories come flooding back. Meanwhile, Lisa scrambles for a special news story in order to save the school radio station.
While trying to relive his glory days, Mr. Burns runs into a mysterious music mogul, who cons him and leaves him bankrupt. To exact revenge, Mr. Burns enlists Homer, Bart, rapper Jazzy James and the mogul’s ex-wife, Praline. Also, Lisa is wooed by the richest kid in town; Smithers undertakes a dangerous trek; and Marge opens an obscure boutique store.
Marge’s obsession with a Japanese-style of living requires the family to ditch items that no longer bring them joy, including Lisa’s beloved saxophone, and forcing Homer to find a home for the family pig.