It's so passe for the good guy to win all the time. Sometimes you want to root for evil, and sometimes, if you're lucky, evil wins (because good is dumb). Here's a list for everyone who may be just a little evil at heart.
The Top 10 Movies Where the Bad Guy Wins,
Fallen
Pay attention to the opening line in the film, and the rest will fall into place. A supernatural entity who can change bodies by merely touching - meaning escape is just a handshake away and also meaning you can't trust anybody. But don't worry, our crafty detective has a plan to beat the demon at his own game. Just when you think the game is up though, that opening line comes back to haunt him.
Identity
A group of strangers find themselves trapped at a desolate Nevada motel during a nasty storm and, wouldn't you know it, one-by-one start dying off. We finds out - SPOILER SPOILER - that these diverse characters are actually all different aspects in the head of one man suffering from multiple personality disorder and that a team of doctors are attempting to reconcile these personality types - both the violent and the nicer types - by ultimately having him "kill" off each one until only one remains. Who wins in the end? Well, if you read the title, you know it's not who you want to win.
No Country for Old Men
Anton Chigurh is not a man you want to mess with. Cold, calculating and deadly serious about completing the task at hand - the perfect killer, which is great when he's working for you, but about the worst possible turnout when he's coming after you. Usually guys like this either turn over a new leaf (ala Jules in Pulp Fiction) or simply wind up dead, but Chigurh finishes his job and walks (well, limps) away to kill another day.
Primal Fear
Usually courtroom dramas leave a bit to be desired - but Primal Fear is one of my favorite exceptions. A stuttering young man accused of murdering a priest - a cut-and-dried case that seems unwinnable, is taken on by a hot-shot lawyer who proceeds to uncover many facets of the story that seems to lead to the boy's innocence. The story really hooks you in - but the big kicker comes as the end - and you really find out whose the player and whose getting played.
Rosemary's Baby
Nothing like giving birth the the antichrist to really just ruin your whole day. Rosemary becomes more and more paranoid throughout the film that her pregnancy isn't exactly on the up-and-up and that two decidedly bizarre neighbors are part of some kind of conspiracy. Normally you would write this off as stress but, wouldn't you know it, in this case Rosemary is exactly right! And, in the end, it pretty much spells the doom of mankind because the devil wins.
Saw
Despite the fact they diluted the francise with many unnessasary sequels, the original films still stands out as an interesting idea. Jigsaw is a man who devises unique forms of punishment for those he deems unworthy - and while these elaborate, deadly traps can be won, it doesn't come without some sacrifice - a sacrifice most people are not willing to make. In our main story two men finds themselves chained in a room, and must play by Jigaw's rules in order to "win" - and by win I mean survive. But in the end, just following the rules may not be enough - and, once again, a kicker of an ending makes us realize that patience is a virtue, even for serial killers.
Seven
Man, Kevin Spacey shows up again - the man is the master of rooting for the bad guy. Anyway, the film revolves around a series of very well-thought out and extremely brutal murders based around the seven deadly sins. You have your classic pairing of veteran cop and hot-headed rookie being paired up to take down the "John Doe" who has decided to put his plans into motion. In the end, despite the detectives thinking they have won the battle, it's Doe who has the upper hand and, even though he may not live to see it, he surely wins based on the outcome.
Star Wars Episode III: Revenge of the Sith
I could have picked The Empire Strikes back (arguably the best Star Wars films) but Revenge of the Sith seems so much more appropriate because The Emperor's plans have been gestating for three films - ever since seeing "young Skywalker" - by the time the Clone Wars have rolled around, Palpatine's in full-on universe-ruling mode, and, like a great villains, is a master at manipulating all those around him. Sure, eventually he does get his comeuppance, but not before wiping out most of the Jedi, creating the Empire and pretty much bringing the entire galaxy under his thumb. That's about as evil as it gets.
The Silence of the Lambs
Hannibal Lecter is a genius - he has a keen mind, and he uses it to his advantage, manipulating all of those around him. Oh, he also likes eating people - you know, brain food and all that. You can say that Buffalo Bill is the bad guy in Silence of the Lambs - and he doesn't win, but Lecter is not the kind of person you want walking around. I mean, when you wheel a guy out in full straight-jacket and a mask to keep him from biting, well, let's just say the man has issues. It's the kind of person who should be locked up - not running around free.
The Usual Suspects
Throughout this entire mind-bending crime mystery, crippled criminal Roger "Verbal" Kint is telling his complicated yet highly detailed story to agent Dave Kujan. The entire story hinges around a mysterious mastermind known as Keyser Soze - a man as enigmatic as he is dangerous. The movie ends on what has to be one of the most awesome twists ever, proving that for evil to win, you have to be as quick-witted as you are ruthless.