51. David - The Lost Boys
Anybody who can mess with my food is definitely evil in my book. David convinces a sad Arizona transplant to eat maggots and drink blood before he can realize what he's doing, initiating him into their vampire/motorcycle gang. Of course, he can also haunt your dreams and never really dies in the end, despite some antlers through his chest - and we all know the creepiest villains are the ones who somehow continue to survive.
52. Damien - The Omen Original
The son of Satan's calm and cool demeanor are where Damien gets his real chills from. This seemingly innocent boy will use everything in his evil arsenal to get his way. And he's got a lot of power being the next antichrist and all.
53. Oogie Boogie - The Nightmare Before Christmas
All the residents of Halloweentown are known for their abilities to spook and scare, but the Oogie Boogie is the only one who is truly evil. With his penchant for sadism and song and his torture of Santa Claus, Oogie provides kids with enough nightmare juice to last through adolescence.
54. Vore - Beastmaster
Don't get too close, or these disgusting creatures will wrap you in their wings and digest you with super spit. You don't stand a chance — unless you're the Beastmaster. And even then, it's touch and go.
55. The Phantom - The Phantom of the Opera
Lon Chaney is frightening in this black and white classic. Of course there have been many interpretations over the years, but Chaney's unmasked man from 1925 is perhaps burned into all of our brains. It's some sort of pig-nosed, pasty demon, and he frightens us.
56. Alien - Communion
Christopher Walken plays hide and go seek with the worlds scariest alien, and if this creature from another world is creepy enough to freak out Walken, you know you're playing with the big guns.
57. Hal - 2001: A Space Odyssey
Sure, HAL's all-seeing eye gave us a great icon for years, but today it's become a frightening reminder not to make computers too smart. The Heuristically programmed ALgorithmic computer turns on his crew with his creepy conversational tone, letting them think he's at their beck and call. But when HAL decides he's running the show, no one safe from his all-seeing, consuming, art-appreciating eye. It's the ultimate fear, a cognizant smart ship with no grey areas. Plus, he sings.
58. The Dementors - Harry Potter
These cold as ice prison guards will suck the life right out of you, tell me the whole theater doesn't seemingly go down ten degrees whenever these floating menaces are on screen?
59. Agent Smith - The Matrix
The only thing humans are afraid of in our super brain plug-in future are agents — that is, until they meet Agent Smith. Maybe it was his strength, his suit, or Hugo Weaving's amazing delivery, full of superiority to our hero, Mr. Anderson — either way, he was a bad ass that you didn't want to mess with.
60. Lord of Darkness - Legend
As the killer of unicorns, he's already not a very popular guy, but add some red makeup and huge horns an the devil becomes a terrifying beast to be killed only by sunlight. But the devil effects aren't the crux of it; Tim Curry's menacing, dark drawl coupled with Yoda-esque English and littered with "doth"s, is what makes the beast so imposing. Wouldn't you flee from a grammatically correct, evil laughter-loving diablo?