When Bart fishes Homer's vintage "Playdude" magazines out of the trash, he decides to adopt the ring-a-ding-ding lifestyle of the 1970s, as interpreted by a 10-year-old. Looking for some action, actor James Caan, guest-starring as himself, drops by Bart's swinging Playdude treehouse. Meanwhile, Marge stoops to sabotage to keep up with the other contestants during the Ovenfresh Bakeoff, attended by the likes of.

Marge runs into her former high school pal Chloe Talbot, who is now a famous newscaster. Chloe is cultured, sharp-dressed and has a successful career on television. While Lisa has become enamored with Chloe's worldliness, Marge becomes jealous and wonders if she made the right decision by choosing family over a career. Blackboard 'Poking a dead raccoon is not research'.