America is all about the anti-hero. From Vic Mackey to Tony Soprano, the deeply-flawed protagonist is all over TV, and the movies as well. The mold for the modern anti-hero is largely Clint Eastwood's "Man With No Name," from the movie of the same title. Eastwood was an outlaw that lived by his own code, had no qualms about droppin' a motherfucker, but was also a decent person at heart, concerned for more than just himself.
The large and small screen have varied this formula widely, but the basic outline is the same. What I find interesting is how popular this type of character has become, and how far audiences will follow him (it's almost always a him), no matter how dark his dark side is:
• Miguel Alvarez, Oz - This might seem like an odd one to start with. If you're going the Oz route, the most obvious choice is Tobias Beecher, but he's not really an anti-hero; he was just a regular-ass dude who got thrown in the worst prison on earth and had to change his code. That's not anti-hero material. Alvarez, on the other hand, had a perverse sense of honor. He felt genuinely bad about letting Fr. Mikada get his ass busted during the S1 riot, and after hacking out a CO's eyes, he spent a whole season trying to make up for it. I don't recall what Alvarez's original crime was, but he certainly wasn't the worst prisoner in Emerald City. (For a brief moment, I considered Ryan O'Reily, but he was a prety malicious guy, willing to do just about anything, and not just when it came to protecting his brother)
• Omar Little, The Wire - I'm sort of trying to go from the "good" end of the anti-hero spectrum to the bad end. In much the same way as Alvarez, Omar Little is a product of the environment he's trapped in. True, he has the intelligence and charm to probably perform well at any number of straight-up jobs, but who's gonna hire him? But unlike Alvarez, Omar - while admittedly lining his own pockets - puts much more of the "hero" in anti-hero, cultivating a sort of Robin-Hood image in West Baltimore. He's also got a quality that helps a viewer digest some of the more squeamish aspects of some anti-hero characters: he's got a quick sense of humor and is always ready with a joke, whether it's genuinely to be funny or to drive home a nasty point.
• Dexter Morgan, Dexter - Again, a product of his environment. You get stuck for two days ankle-deep in blood in a warehouse with your mom's corpse? Who can blame you for becoming a serial killer? But taking his job as a Miami PD blood-spatter analyst and subverting the "serial killer who kills other serial killers" cliché, it works very well. He only goes after bad guys, his deadpan narrative is fucking hilarious, and he has genuine concern for people in his life, even if he struggles to feel true emotion.
• Marv, Sin City - You would think it'd be tough to feel for Mickey Rourke's G-Unit Frankenstein, Marv, yet you do. And here we come to another attribute the anti-hero is famous for, the Largely Purposeless Moral Mission. I suppose you could call it a "devil's errand." Vic Mackey did a lot of this stuff in the first few seasons of The Shield. He had a weakness for prostitutes. Not for fucking them, but for helping them if they were truly in a tough situation (more on that later). Marv is on a mission to avenge the death of a hooker. No real good to be had in that, only vengeance and a perverse sense of justice. Just what we want in our anti-hero.
• Al Swearengen, Deadwood - In the first season of the greatest Western serial ever (fuck Bonanza... for real), the cocksucker-droppin' Gem Saloon owner is involved in a situation that typifies the modern anti-hero. These characters are navigating a brutal, nasty world, and a writer's dilemma is how to show that, show these men doing evil things, yet have an audience still feel for them and care what happens to them. Swearengen finds out that a coach of Swedes ("squareheads," in his words... that might be my favorite racial slur... who knew there even WAS a racial slur for Swedish people?!?) has been attacked by men he hired, and a whole family has been killed. He's PISSED (he's basically pissed for the entire series). And sure, it's mostly because he's got to find a way to diffuse the situation and deflect blame from himself, but he also reams the men out for having killed a woman and her children.
• Tony Soprano, The Sopranos - There may very well be another character from The Sopranos that would fit better on this list. Because when it comes right down to it, Tony Soprano was pretty much a self-absorbed, narcissistic dick. He did act out of concern for his family, but he also tried to force his 1950s mentality on them. He had this idealistic image of what his family would be like when he was boss of the Soprano regime, and it could not have worked out more differently. At the same time, he was in charge of an arcane organization that didn't jive with his modern problems. He was a man adrift in two worlds.
• Porter (Mel Gibson), Payback - Porter is a criminal, plain and simple, but he achieves anti-hero status by sticking to his principles and the code of honor among thieves. All he wants is his money, and these Company pricks whose lackey double-crossed him and left him for dead won't give it up. An anti-hero's willingness to turn on old criminal friends in pursuit of his brand of justice is also one of the characteristics that helps endear him to audiences. He might be a bad guy, but he's perfectly happy to take on badder guys.
• Vic Mackey, The Shield - Mackey is at the "bad" end of the spectrum because, plain and simple, he's a dirty cop. He used his badge for personal monetary gain, to hurt people, to frame others, and ultimately to kill people. But before he became a cornered pit bull in the last couple seasons of the series, he was a bad cop who did a lot of good things. He got a lot of drugs off the street. True, he sold some back to other dealers in exchange for peace on the streets, but most of the time, he was looking at the big picture, at the amount of good he was doing vs. harm. Even when he and the Strike Team were planning to hijack the Armenian mob, he justified it as any good anti-hero would: "They got this money from dope-dealing and whoring... they didn't earn it, and I don't feel bad about taking it." And you can't help but feel a little bit of sympathy, because A) the local Armenian set loses about six months' of profit, and B) he and his team will be able to take care of their families if something were to happen to them. He had a strange symbiotic relationship with a hooker named Connie for the better part of two seasons, helping her because, despite being a ho, she had a young son and Mackey wanted to see him taken care of. But while he did do plenty of valiant things, at the end of the day, Vic Mackey's main concern was Vic Mackey. His family, too, but mainly himself. In some ways, Mackey tells the story of a developing anti-hero. Most of them are loners, but Mackey tried to surround himself with allies. In the end, though, he threw almost all of them under the bus, and ended up completely alone.
Lemme know who I am leaving out. I figured I'd cap the list here.