"You know what? Fuck you! How about that?"
Tony Montana refuses to see the world as anything other than exactly what he wants it to be. He is so uncompromising that, even at film's end, as he is defiant and riddled with bullets, we get the sense that no lesson was learned. He fought his way to top on nothing but bluffing and persona, and his ultimate fall came because he refused to compromise on his belief systems. He was never afraid of Sosa, the cocaine king he betrayed, but maybe he should have been. He wouldn't be Tony Montana in that case, however.
Tony Montana is a dark, inverted reflection of the Horatio Alger story. We want to be like him in his success, but we are repulsed by the things he does to get there.
9. Garland/Chaos (Final Fantasy)
"I will be reborn again here. So even as you die again and again, I shall return! Born again into this endless circle I have created!"
I consider Garland's story in the first Final Fantasy game to be a simple masterstroke of weird fantasy storytelling. A petty knight with delusions of grandeur, Garland is easily defeated and cast aside in the game's very first dungeon. Then, after the heroes have travelled thousands of miles, defeated the Fiend of the Elements themselves, and then gone four thousand years into the past they find themselves facing Garland once more. He has outsmarted them and merged himself with the fiends to become the dark god Chaos.
By defeating Chaos, the heroes undo the events of the game and destroy all memory of their heroism.
8. Marlo Stanfield (The Wire)
"Let them know Marlo step to any motherfucker -- Omar, Barksdale, whoever. My name is my name!"
Marlo Stanfield is the lord and master of his own tiny crime fiefdom within Baltimore. He is ten times as ruthless as his predecessor, Avon Barksdale, and like Tony Montana he has no fear. He begins as, in some ways, an allegory for the Iraqi insurgency against the American army, and ends the show embodying the seedy, dark side of Baltimore that can never truly die or be put out of sight.
He isn't as clever as Stringer Bell, Avon Barksdale's right hand man, but in the end, his cruelty and power catapults him to legitimacy. Legitimacy was what Stringer Bell wanted, but it suits Marlo poorly. His last scene is perfection - dressed in a suit he assaults two men on a street corner, drawing his own blood in the process. He simply cannot be "good".
7. Nyarlathotep, the Crawling Chaos (The Cthulhu Mythos)
"And it was then that Nyarlathotep came out of Egypt. Who he was, none could tell, but he was of the old native blood and looked like a Pharaoh."
Nyarlathotep is perhaps the only deific being within the Cthulhu Mythos that could be rightly considered a villain. Whereas the Great Old Ones are unaware of humanity, Nyarlathotep makes it a part of his mission to mess with humanity on grand scale. He is the Mythos' version of Satan, but unlike the ruler of Hell, Nyarlathotep is unrestrained in his actions. There is no benevolent deity watching over. There is only Azathoth, the blind mumbling Lord of the Universe, who Nyarlathotep serves and hates.
Wherever there is an opportunity to aid humanity in destroying itself, Nyarlathotep will be there. In the end, Nyarlathotep is destined to destroy the Earth, and so his sadistic manipulations of humans is purely for his own pleasure.
6. Sovereign (Mass Effect)
"You exist because we allow it. You will end because we demand it."
Sovereign is what Cthulhu could be if he would only stop being such a pussy. Delivering a masterpiece of a villain monologue, Sovereign, the leader of an advanced race of synthetic beings who have secretly created and destroyed civilization within the galaxy uncountable thousands of times, informs the player that (s)he is an insignifant mutation next to the awesome grandeur of the eternal Reapers. And we believe him!
His eventual defeat comes at the hands of Commander Shepard, humanity's greatest hero, and at the cost of most of the united galaxy's warships. (There are breathtaking scenes here where Sovereign literally smashes apart enemy ships with his own frame, not even slowing down.) And yet he is only one among thousands of his kind. Ominous.
5. The Joker (Batman)
"They said I was sick in the head. They said I needed help. Well, maybe I'm a little Batty blame it on the Bats in my belfry!"
Joker would not be a great villain were he not the enemy of Batman. The hero-villain synergy of the two is without parallel. The Joker is a laughing force of chaos and destruction, Batman is a solemn defender of law and order. Much like the forces they represent, Batman and the Joker need each other to have existence and meaning. The Joker was Batman's first notable adversary in the 40's, and he has remained his most famous enemy ever since.
The Joker is mad, and his story remains an enigma. I do not believe that any backstory every crafted to explain the Joker's origin has been wholly satisfactory. He is ever ruthless, cruel, and unpredictable.
4. Cigarette-Smoking Man (The X-Files)
"Don't try and threaten me, Mulder. I've watched presidents die."
The Cigarette-Smoking Man is the embodiment of "The Man." He is the American Darth Vader for the 90's, and the dark force whispered about in conspiracy theories, the man who really pulls the levers of power behind our massive government.
He killed JFK, assasinated Martin Luther King Jr., and made sure the Bills never won the Superbowl. He is behind everything, and, seemingly, nothing. He is all implied menace and power. He won't shoot you himself, but if you cross him no doubt you will end up with a bullet in your brain.
3. Michael Corleone (The Godfather Parts I and II)
"That's my family, Kay, it's not me. "
Michael Corleone's story, like that of Anakin Skywalker, is one of corruption and failure to live up to ideals. How does a man with a good nature who despises his family's criminal enterprises become a soulless Mafia don who has nothing but his power and wealth to comfort him? The Sicilian values of honor and family draw Michael in, but we get the sense that there has always been something dark inside of him that makes him truly GREAT at being a criminal mastermind. He is cold, calculating, and ultimately and unbeatable adversary, even for such seasoned gangsters as Hyman Roth.
At the end of Part II, as Michael sits in silence at his Lake Tahoe compound, we get the sense that his commitment to his life as an evil man is full, and that his regret and humanity is buried deep down where it will never return. He has lost everything.
2. Darth Vader (The Star Wars Saga)
"I find your lack of faith disturbing."
Darth Vader's story of fall and redemption is the story of Star Wars. During the films, Anakin Skywalker plays every role from innocent provincial slave child to galactic Dark Lord. Vader is tragic, powerful, and always compelling. His destiny is never in his own hands until his final choice at the end of the saga, but his Tragic Hero arc plays out on such a large scale that he bestrides the galaxy like a colossus. He is a man who will murder children, watch planets die, and sacrifice his life for his son to put an end to the legacy of his own actions. In the end, unlike Michael Corleone, Vader still has a soul to save.
And he is pretty menacing in black. Vader's characteristics have become shorthand for villainy in modern pop culture.
1. The Emperor (The Star Wars Saga)
"Your feeble skills are no match for the power of the Dark Side!"
Were the question, "Who is the most compelling villain?" Darth Vader or Michael Corleone might have topped the list. The question, however, is "Who is my favorite villain?". The Emperor has no deep character traits beyond his cackling, hateful menace. He does not go through an emotional arc within the saga. He is pure, arrogant, dark black evil.
The Emperor is Satan's slightly more evil and infinitely more capable brother. He is utterly ruthless, and will not hesitate to kill off his apprentices for his own benefit. In a religious order where succession by the apprentice is the natural order, the Emperor has maneuvered in such a way as to be beyond challenge. Beyond his potent physical threat, he is a dark genius and a great judge of character. The Emperor is a complete embodiment of the dark sorcerer pulp villain, who lives only for power.