Here's my five, of movies and literature, in no particular order: 

Bill the Butcher, [i]The Gangs of New York[/i]: He's a cruel, twisted man but damn if he's not charasmatic. A bad guy who also has a code of rules he abides by. He was played so well by Daniel Day Lewis I was not mad when he took revenge on Leo Decaprio's character ( I don't even remember that guy's name). 

Saruman the Wizard, [i]The Lord of the Rings[/i]: One of the wise, the highest ranked of the immortal Maiar and yet tempted like any man with promises of incredible power, knowledge, and treasure by Sauron. I chose him over the Eye because he was supposed to be good, to watch over Middle Earth and instead he lay waste to it and was responsible for the death of untold amounts of people and the invasion of the Shire. 

Napoleon, the Pig, [i]Animal Farm[/i]: Leads the revolution of farm animals against their masters and ends up betraying them and becoming what he supposedly was against. The story of so many so called revolutionaries. I wanted him turned into bacon when I read this book back in school. 

Nurse Ratched, [i]One Flew Over the Cuckoo's Nest[/i]: Whether you saw the movie or read the book, she is the personification of how evil and petty and abusive people in a position of power can become. 

Patrick Bateman, [i]American Psycho[/i]: When I first read this book, I couldn't get past the first real violent scene with the blind man and the dog. I don't believe I've ever read a book in which I hated the main character so much.