The reason this movie is so brilliant is because it works on two separate levels: the actual storyline of the movie, wherein a reformed killer in the Old West goes on a quest to murder two men who mutilated a prostitute; and the higher plane, where that storyline is used to shatter myths about an entire genre of entertainment, as well as an important period of time in our country's history.
Like any good classical Hollywood cinema, the catalyst moment happens within the first few minutes: two cowboys cut up a hooker. The hooker was new to it, and hadn't ever seen a flaccid penis, and laughed at it. Like another great western, BROKEBACK MOUNTAIN, this movie explores how the traditional American man mutes all his emotions to squeeze them into anger and rage. In this case, the john was embarrassed, and chose to show that through anger. And so he destroyed someone's face as a result.
This is a man's world, and the women are property, so the only result is that "Skinny gets some ponies?!"
And now we see William Munny. A stranger comes to town. He's "The Scofield Kid", and he's heard the legends of Munny, wants to partner with him to kill the men for the reward the hookers have started to rustle up.
Debate: Munny refuses, but the subtext is that he is not really a hog farmer at heart, and he also desperately needs the money. He goes and forms his posse with Freeman as act 2 begins.
Set piece: Richard Harris is English Bob. His scene serves to show the ways in which power is exhibited by violence during this time. It's also a setup about the main conflict in town, which is that the sheriff and his men are the only ones allowed guns, and anyone else will be beaten. English Bob shows power through his insults about the president and through his flaunting of his hidden guns; Hackman shows his power by stripping away Bob's through violence. By extension, he shows his power to the hookers, to get them to call off their reward.
Munny and Ned meet up with The Kid, who can't shoot. He's all talk. They near town.
English Bob is in jail, and his biographer, Beauchamp, is working on "The Duke of Death". The myths about the Old West were already around
during that time due to men like Beauchamp. Little Bill dispels the myths. He's didactic about it, but we buy his exposition in dialogue, his almost aside to the audience, because he's deflating a foe's ego while talking to a naive character (Beauchamp is a surrogate for the audience -- we learn while he's learning).
Besides, in learning, we get a great suspense scene about how fast drawing isn't what it's cracked up to be. It's more important to be accurate. And more importantly, we learn that (especially if you aren't drunk), it is difficult for anyone to make the decision to kill a man. Even if that man is the only thing stopping you from getting out of jail.
Midpoint -- Beauchamp is now with Little Bill, at his house, his biographer now. Munny and posse arrive in Big Whiskey, their guns on them. Little Bill comes to strip them of their guns, beats Munny to a pulp as the other two escape.
The set piece detailing the killing of the first cowboy happens in a beautiful canyon, and there's nothing glamorous about it. Even though he's a villain in the movie, he didn't actually do anything to the girl (he was just the cutter's friend), and even brought an extra pony for her. In many ways, he's a victim. But he's got a price on his head, so he is sniped. But he doesn't die quickly, he dies
slowly. He's crying for mercy, for help. He's thristy. He's human.
Ned gets nervous. He doesn't have the taste for killing anymore, leaves, is found by the lynch mob that forms after learning about the murder of the first man. Freeman is tortured and killed by Little Bill.
The second man, the one who actually did the cutting, is killed by The Scofield Kid while in the outhouse. Two things to consider: The Kid is jittery as hell while doing it, and he murders the man while he's taking a crap. And he's the one who's supposed to be a hero?
Eastwood is back to drinking, and no wonder. "It's a hell of thing killing a man. You take away all he's got, and all he's ever gonna have."
They get the reward money and learn that Ned's dead. Thus ends act 2.
In act three, all bets are off. Munny is drinking again, he's got a taste for killing again, and he's got a reason to kill now. He claims he "ain't like that no more" and that he mostly used to kill because he was a mean drunk, but now he's killing for revenge.
One brilliant thing about this movie is the arc of Eastwood's character: he seems a broken man, haunted by the weight of the wrong he did in the world, reformed due to the love of a good woman but shouldered with the burden of her death and his need to raise his kids as a single father. He seems old, tired, beaten, and we almost don't believe the stories Ned and The Kid tell about how he used to be a cold-blooded killer, a ruthless man.
But then he comes back to Big Whiskey. And kills
everyone. Beauchamp is excited to see a real myth in action, an actual bad man. Now he's got something to write about that's better than his embellishments.
Think about the ways this movie shatters our illusions about the romance of the Old West and Westerns in any medium: angry, almost psychotic men ruled everything; people like the Scofield Kid bought into myths and tried to live them out; drunkeness was the cause of so much of the violence; being a fast draw didn't mean as much as we think it did; horses aren't that easy to ride; the game of telephone used to embellish the hooker's injuries ("cut her eyes out", etc.); a supposed gunslinger who needs
glasses, of all things; blacks and Indians as real characters, instead of background or villains; the treatment of the killings of the "villains"; the uprooting of the kind of characters Eastwood himself used to play. All brilliant.
More troublesome, however, is how the movie literally puts women into those two demeaning camps: Madonna (Munny's wife, now dead, who reformed him, and is seen as an angel) or whore (the prostitutes, who disobey the man who owns them, who give out "free ones" in advance of the killings they ordered). This is a man's world, that much Eastwood and Peoples could not deconstruct.