3. Joseph Fitzgerald O'Malley Fitzpatrick O'Donnell The Edge "Joe" Quimby (The Simpsons)
One of only two Mayors on this list to be wearing a sash that says "Mayor" at all times, in true Mayoral fashion, Quimby always comports himself in a manner befitting€“ "Quick! Honk at that broad!" Basically a parody of Ted Kennedy, no matter how corrupt he is, no matter how many scandals he's involved in or tax dollars he embezzles or paternity suits filed against him, Quimby will most likely be Mayor of Springfield for the rest of eternity.