4. Mayor Quimby
Along with Family Guy's Mayor West, the JFK-referencing Mayor Quimby is part of the greatest double act of Mayors in animation history, and like Chief Wiggum, there are considerable doubts over how he climbed to his lofty position, considering how comically unsuited he is. But, Quimby is the epitome of the sleazy politician, corrupt to the last, and willing to sell out anyone or anything, as well as being lecherous and adulterous in spades: he is another triumphant grotesque portrait aimed at poking fun at real figures and playing on viewer expectations of political stereotypes. Quimby has very few redeeming qualities, even when he's shown at his most vulnerable, though he does occasionally have moments of genuine virtue, even if they are few and far between. Again, Quimby's appeal, and his ability to steal scenes comes from the performance behind him - he is slimy, charismatic and utterly irresistible, as you would expect from his breed of politician, and his willingness to break rules and philander is ridiculous, and almost worthy of praise in itself.
Select Quote: "Chat away. I'll just amuse myself with some pornographic playing cards."