Gollum, Lord of the Rings- The mislead poor creature who wants to help his friends, or the malevolent monster with a corrupted mind, who wants the ring all for himself? Undoubtedly suffering from schizophrenia, Gollum/Smeagol is one of the most interesting villains of all time, being a crook, a murderer, and a helpful navigator all at the same time. Half the time he can't even remember who is, or used to be, only that there is something that he dearly needs, and it was stolen from him. Yet as Gollum begins his journey to retrieve his precious, something starts to show inside of him, whether it is remorse or sorrow or just plain guilt-or is it any of those at all? One minute you feel sorry for him, and the next you hate him, and wish that he would just fall into a fiery pit. No matter which it is, though, Gollum makes you think, through riddles and clues hidden in plain sight, and can reflect the minds of ourselves at times. 
Cal Hockley, Titanic- No Titanic drama would be complete without a love angle of some sort (it's an angle, not a triangle. Try to draw one and you'll see what I mean), a scandal that was considered the end of the world in 1912, or a crime on board. James Cameron's 1997 Titanic has all of those (which is probably why it won so many awards from a modern audience), but the character that really makes all these pieces fit together is none other than the miser Cal Hockley, or as I call him, Count Rubenstein, which is a really long story. Obsessed with money, even though he already has an ample supply, Cal is engaged to the beautiful, young Rose DeWitt Bukater, who despises him despite what her mother says. It soon becomes apparent that though he buys her jewels beyond her dreams, he doesn't care for her either, or at least not as much as he cares for money, even though it is their marriage that will solve the Bukaters' problems. After several sneaky attempts to shake off the young and poverty-stricken Jack Dawson, Cal resorts to shooting at the couple, leading them (again) to their almost-deaths. After realizing that his diamond is gone, he goes off and steals a child to allow him onto a lifeboat. How many arrest counts would there be there? It's hard to find any mercy to show him, and you're almost happy when you find out that he killed himself a few years later. The curious thing about Cal, however, is that he's not evil just for the sake of being evil. He's evil because he's a jerk, and it's as simple as that. Now would be a really good time to tell you that there are probably some major spoilers in this. If you haven't seen Titanic, then shame on you (just kidding. Maybe). But if you haven't seen the faces in the pictures, then don't read it. Or if you have, and don't want to know what happens next, then DON'T READ IT.
Hilly Holbrook, The Help- There's no way that you could
charge Hilly with anything in specifics, since she was living the life that probably thousands of young women did in the 1960's, but there's something that just can't stop you from hating her. So sure that her race is superior, far above that of her maids, she goes to great lengths to stop them from getting the correct treatment, and even greater lengths to make sure they get the worst treatment. Hilly is obsessed with herself and her reputation, and will stop at nothing to ensure that it is stabilized, even if it includes drafting her own bill to require a "black" bathroom for the maids in a white home. The horrible thing that you realize about this book/movie, however, is that Hilly did so many horrible things to the people in Jackson, but there were so many others like her, and those stories didn't have happy endings.
The Master, Doctor Who- I'll have to admit, the Master is one of my favorite villains, just because he's so completely psycho. After regenerating from the form of the old Professor Yana, locked away in a body, forgetting who he really was, the younger-looking new incarnation sprung up from the ashes, looking like a maniac. The next time you see him, he's the prime minister of England, and starts inviting aliens to Earth. After that, he pops up again about a year later, with a giant craving for food, which leads him to start muttering to himself, which leads to a schizophrenic psychopath breakdown (I seem to like schizophrenic characters). What I find interesting about the Master, though, is that in his second appearance in the new series, he's so much different, and you realize that he may not be as evil as you think he is, just really messed up and willing to kill everybody on planet Earth. He's been insane ever since he was a child, and you have to give him credit for that, especially when the most unlikely possibility turns out to be the new villain. Still, you can't forget what he did to the Doctor and so many others before (in short, torture), and you have no room in your mind for remorse for weirdos. Hitler was messed up, too. 
Bellatrix Lestrange, Harry Potter- Speaking of pyschopaths.... :) There's a reason that I'm not writing about Voldemort, and it's that he's way too obvious. The most popular villain of all time, yada yada yada. It's true that Bellatrix is kind of overdone, too, but she really is just crazy, and that's what makes her so interesting. While she was so horrible to the rest of the world, Bellatrix is one of the only known female Death Eaters, next to Narcissa Malfoy, who would never even come close to her sister's rank. She considers herself Lord Voldemort's greatest worker, although Tom Riddle had never worked well with others, and doesn't have the ability to love. Many Harry Potter fans love Bellatrix Lestrange, thinking of her as the epic evil force with the cool hair, but what she has done cannot be undone. She remains to this day one of my favorite Death Eaters, but I really, really would not want to bump into her in a dark alley. 
Ha, ha, this is who I should have done. But then there would be six antagonists, and five is a good round number.
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