91. Henry - Henry: Portrait Of A Serial Killer
Played By: Michael Rooker Henry is perhaps the most disturbing example of an evil protagonist as he has no likeable qualities or redeemable features, he is, as the title says, an unadulterated serial killer. Henry possesses inhuman attributes and is depicted by Rooker to the extreme as his sociopathic ruthlessness got increasingly more disturbing culminating in the massacre of an entire family. The film is a difficult and chilling watch thanks to the brutal nature of the titular character. It may not be filmed like a typical horror film but Henry makes Leatherface look like a fluffy bunny in comparison. It's a shame so few people have seen it because it's incredibly harrowing.
90. Cyrus Grissom - Con Air
Played By: John Malkovich Con Air is the perfect example of a movie so bad it is actually great. It is cliched, inconsequential and features Nicolas Cage doing one of the most absurd accents ever recorded, but yet it is insanely watchable - much of that is down to John Malkovich's darkly comical Cyrus Grissom. Cyrus has endless amounts of quotable dialogue and his manic intensity is equal to the sweating desperation of Nic Cage's character as they battle for their respective causes. He is an evil genius and despite being on a plane full of menacing characters such as Ving Rhames, Steve Buschemi and Danny Trejo, he is still the most psycho, hell bent on escape and creating as much havoc as possible in the process.
89. Brick Top - Snatch
Played By: Alan Ford The snarling kingpin rules over East London with a fearsome reputation and a farm full of hungry pigs. He looks unsettling with his crooked teeth, large glasses and garish dress sense but he's a monster and if you cross him he will throw you to the pigs. He has control over the underground boxing ring, making sure the matches are rigged to make the maximum profit for him and whoever he wishes to please. He's not above the cold-blooded murder of innocent citizens either. It is inevitably, his aura of invincibility that causes his downfall.