Really, really dark anti-heroes.

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WARNING: The following post contains major spoilers about Giftorcurse's favorite movie ever, To Live and Die in L.A.

Ask me about a really dark, messed-up anti-hero, my response will be Secret Service agent Richard Chance from To Live and Die in L.A., which you may know by now is probably my favorite eighties movie... ever.

Basic plot of TLADILA is this: Willem Dafoe kills this guy's partner. This guy is not happy. This guy uses a female parolee as his CI/personal hooker to get information on Willem Dafoe. This guy treats his new partner like crap, and engineers a stick up of an undercover FBI agent to get money for his sting operation against Willem Dafoe, which leads to a car chase that endangers many lives. This guy eventually gets his face blown off with a shotgun, and Willem Dafoe gets away in death.

Damn. I guess that's one way of saying that William Petersen has issues in this movie.

Parker from the novels by Richard Stark (Donald Westlake) is the anti-hero to end all anti-heros. He's not so much an anti-hero as a villain who happens to be the hero. He lies, cheats, steals, and kills, and doesn't really care who gets caught in the crossfire. The movies water him down, of course: the trailer for the new movie Parker starring Jason Statham has him saying things like, "never hurt anyone who doesn't deserve it, and never steal money from anyone who needs it," but the Parker of the books is the kind of guy who would steal money from a homeless beggar's cup and break his neck if he tried to do anything about it. Although the movie Payback with Mel Gibson (the Director's Cut, at least) was a bit better in that regard: it featured a scene just like the one I described, and many worse ones. It's worth a watch.

The first dark antihero who comes to mind is Alucard from the anime/manga/OVA series Hellsing. As soon as his master Integra gives the order, he will brutally slaughter anyone she tells him to, such as the time that he morphed into a hellhound and ate Luke Valentine. He also impaled Rip Van Winkle on her own musket. These are just two instances of many in the series showing how brutal he can be. It's never made clear as to why he's on the "good guys" side, but if he belonged to one of the two "bad" organizations in the series, he would probably be considered one of the most effective villains in anime history.

Two other dark antiheroes that come to mind are Sweeney Todd and Mrs. Lovett, from the movie Sweeney Todd. They are less heroes than villains whose story we follow throughout the movie. He slits peoples' throats, she bakes them into pies and sells them to people. Sweeney Todd sings a song about how everyone in the world deserves to die, and it's implied that Mrs. Lovett wanted to kill Toby after she realized that he was catching onto her and Sweeney's activities. Mrs. Lovett also withheld a key piece of information from Sweeney about his wife throughout the whole movie that wasn't revealed until the end.

I consider Walter White from Breaking Bad to be a superb anti-hero.
He starts out like a troubled hero (or maybe neutral protagonist), and gets progressively more and more ... evil.
Other anti-heros have done worse things, but few have their sinister actions so elegantly linked to desired outcomes.
Unlike so many other dark orchestrative killers, he does nothing for whim, sport, or spite.
--[-SPOILER ALERT-]--
The endings to seasons 2, 3, and 4, are each punctuated by a more poignantly evil deed from Walt.
At the end of s2, he watches and waits as Jessie's girlfriend chokes to death on her own vomit in her unconscious heroin stupor, and lies to Jessie about it afterward.
To save himself at the end of s3, Walt orders the murder of Gale Boetticher, a diligent, intelligent character who dies both innocent of any wrongdoing and ignorant of the feud which provokes his death.
The end of s4 reveals that Walt had poisoned an innocent child to the brink of death, to get Jessie and Gus to arrive at a particular hospital at a strategic time.
I have not seen season 5 yet, but I expect Walt will become even more Machiavellian and callous over time, culminating in some catastrophic tragedy.

Read James Elroy's fiction - his books are full of anti-heroes. For anyone who's seen the movie L.A. Confidential, which was inspired by Elroy's book of the same name, you'll recognize the three lead characters could easily have been the bad guys. The main difference between the book and the movie was, I wanted all three in the book to die.
But my favorite Elroy character has to be Pete Bondurant. He was originally a minor character in White Jazz, but was bumped up to a main character in American Tabloid and it's sequel, The Cold Six Thousand. Bondurant starts off as Howard Hughes' body guard and dope procurer, as well as a hitman for the mob in the late 50's, early 60's. He and other characters become drawn into the CIA's/Mob's sinister plots involving the training of right wing Cuban exiles for the Bay of Pigs invasion, as well as political murders. Bondurant starts out as seeing communism as bad for business, and nothing else, and sees his involvement as a way to make cash. In the end, he is a professional anti-communist, and fire breathing Anti-Castroite. In American Tabloid, Bondurant seems to regain his soul at the end, though by the end of The Cold Six Thousand, I'm not so sure, anymore.

-Bill, otherwise known as Kraichgauer