9. Sideshow Bob - The Simpsons
FoxRobert Underdunk Terwilliger, PhD more commonly known as Sideshow Bob is the best known antagonist of The Simpsons and has been terrorising Springfield since 1990s episode The Telltale Head. The last 24 years of Bobs life have been spent trying to fulfil his consuming vendetta against ten-year-old Bart Simpson. His target may be a young boy who is yet to comprehend the gravity of some of his more annoying actions but Bob still never shows any remorse at trying to kill a child. Though he has been thwarted on every occasion, Krusty the Clowns former sidekick exhibits many psychopathic qualities. He is extremely grandiose and theatrical often his schemes to kill off poor Bart are undone by their excessive complexity as Bob attempts to prove his diabolical genius. Indeed, if Bob were to just use more conventional methods he arguably could have exacted his revenge a long time ago. Since the early years we have seen Bob start a family, however he has indoctrinated his spouse and young child to be obsessed with killing Bart also.