When Milhouse's parents are lost at sea and presumed dead, Milhouse decides it's time to begin acting like a real man, and his new attitude makes him more attractive and popular than ever. Bart can't stand that Milhouse has become cooler than him, and he devises a plan to win back his cooler-than-Milhouse status. Meanwhile, Homer finds himself in hot water when he can't remember the color of Marge's eyes, and Marge vows not to let Homer see her eyes again until he remembers their color.

Kelsey Grammer returns to guest-voice as the infamous Sideshow Bob, David Hyde Pierce as Sideshow Bob's dubious brother Cecil Terwilliger, and John Mahoney as their father, Mr. Terwilliger. Marge dreams that Keith Olbermann (guest-voicing as himself) chides her for fast-forwarding through television commercials. Marge tries her to make restitution by watching hours of advertisements, and she and the Simpson family take particular interest in an ad for Wes Doobner's World-Famous Family-Style Rib Huts. They drive to the restaurant, only to find Sideshow Bob waiting for them, triumphant in his elaborate hoax to lure them to their doom. When Sideshow Bob's attempt to terminate the family is foiled, he is put on trial, where his father blames Sideshow Bob's psychosis on Bart. During the proceedings, Bart accidentally kills his old nemesis, and Bob's brother Cecil invites Bart to attend the memorial service for Sideshow Bob to bury the hatchet for good.