The Simpsons (1989): Season 17, Episode 8

17 - 8: The Italian Bob

After Mr. Burns crashes his Stutz Bearcat, he sends Homer and the family off to Italy to pick up his new fancy sport car. While on their Italian adventure, the Simpsons end up stranded in a small Italian village where a rehabilitated Sideshow Bob reigns as mayor. Sideshow Bob impresses the Simpsons enough so that they keep his sordid past a secret until one of the family members, in a wine-induced state, spills the beans.