You give wonderful examples, but I do believe that nothing reaches the depths of Iago from Othello. People can write characters with ambition, lack of morality or just coming from the depths of Hell.
Yet, even when you just read the play, one can taste the seething hatred Iago has for Othello. He is brilliant, conniving and driven. I seem to hate myself for understanding him every time I see the character acted on stage.
That's a tough one. I've read so many books that I can't just pick one. I think my favorites would have to be Lord Voldemort from Harry Potter, the Star Snuffer from So You Want to be a Wizard, Dr John Dee from the Secrets of the Immortal Nicholas Flamel series, and General Argelin from Oracle Betrayed.
My personal favorite is Hannibal Lecter. He is such an intricate and carefully developed character and he fascinates me. He is viewed as a villain because of his cannibalistic practices, but at the very end of the series he is almost transformed into a hero when he rescues the hero, Clarice Starling, from her death and the two fall in love.
It's a non-traditional story and really makes you question the difference between hero and villain.
Darth Revan from the Old Republic time period of Star Wars. Not only is the reveal of his identity legendary in video games, he walks the line between hero and villain so much better than a lot of characters. I think most players would follow him regardless of which side of the force he fell on.
Oh, probably Dracula. "Welcome to my house! Enter freely and of your own will!...Go safely, and leave something of the happiness you bring!" - yeah, well you forgot to mention that part about not letting him go! Dracula was so, so evil!
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