7. Sideshow Bob
A well-spoken, cultured criminal mastermind, self-proclaimed genius and former sidekick to Krusty the Clown, Robert Terwilliger was arrested after Bart and Lisa exposed his plan of robbing the Kwik-E-Mart and framing Krusty. Since then hes sworn vengeance on Bart and tried to kill him in various elaborate ways over the years, only to fail and end up back in the slammer. When he does rarely catch a break, like becoming mayor of a small Italian town, falling in love and having a son, its usually ruined, often by the Simpsons.
6. Troy McClure
During the 1970s, Troy McClure was a successful actor on the stage and screen. But he fell on hard times after a scandal involving extra-curricular activities with fish, and was reduced to presenting infomercials and poor quality educational films like Two Minus Three Equals Negative Fun! and Fire Crackers: The Silent Killer. Never one to lose his enthusiasm, his come-back came when he landed the leading role in the musical Stop The Planet of The Apes! I Want to Get Off! after a sham marriage to Selma Bouvier revived his career.