5. Becoming Mayor (Again) & "You Can't Handle The Truth!"
Long before he became mayor of a small Tuscan village in Italy, Sideshow Bob once ran for, and won, the role of mayor of Springfield. In the 1994 episode "Sideshow Bob Roberts", Bob is released from prison and is named as the Republican candidate for the Springfield mayoral election. Determined to thwart him (as ever), Bart and Lisa vote for mayor Quimby, but it is all in vain as Bob wins by a landslide. This is bad news for the Simpsons family, who soon learn that their house is in the way of Bob's plans to build an expressway, and that their home will be demolished, leaving them homeless. After discovering that Bob rigged the election, however, Bart and Lisa foil the new mayor by revealing that the majority of those who "voted" for him are long-dead. This episode is choc-full of wonderful Bob moments. His devious plan to ruin the Simpsons, his dabbling in politics and the wonderful quote: "You can't handle the truth. No truth-handler, you! I deride your truth-handling abilities!" all make this a winning Sideshow Bob-fuelled half hour of television.