The Simpsons: Every Sideshow Bob Episode Ranked Worst To Best
13. The Italian Bob (Season 17, Episode 8)
In this globe-trotting episode, the Simpson family travel to Italy to pick up a car for Mr. Burns, only to find the town they're visiting is run by the long-missing Sideshow Bob, an elected mayor who now has a wife and son.
The Italian Bob features of handful of effective gags (Bob's elected mayor because he's great at crushing grapes with his abnormally large feet), but its decision to make the career criminal a family man feels out of place, and leaves Bob feeling oddly reigned-in compared to his earlier appearances.
A Sideshow Bob episode with no twisted schemes, an unresolved ending, and a long-winded if dumb-fun final stretch, The Italian Bob honestly feels like it was made without any inclination of what it was aiming for.
Most of Sideshow Bob's episodes have some bigger, funnier plan at play, but not this one. Bob, much like The Simpsons itself by this point, is losing his touch.