Robert Underdunk Terwilliger, AKA Sideshow Bob.
After framing Krusty the Clown for armed robbery, he hosted his own kiddie-show, Sideshow Bob's Cavalcade of Whimsy. But Bart Simpson foiled his schemes for world domination and a Parent's Choice Award. Thus Sideshow Bob became Bart's nemesis, an implacable and fiendishly clever embodiment of pure evil.
Through his charm, brilliance and consummate acting skill, Sideshow Bob repeatedly gains release from prison and devises diabolical schemes of revenge, only to be tripped up by his own fantastically inflated ego - and the occasional garden rake.