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  • Accidental Aesop: Neither Clint Eastwood nor screenwriter David Peoples intended to make an anti-violence film. It was simply a by-product of the script.
  • Alternative Character Interpretation:
    • Is Little Bill a genuinely good sheriff who just uses some very harsh and questionable methods, or is he just a sadist who uses the position of sheriff as an excuse to embrace his former outlaw side, and doesn't care about the law if it does not give him a chance to become violent. The film paints him as the latter, but there is some evidence for the former.
    • While Ned was not written to be black, and Morgan Freeman just lobbied for the role, Little Bill's decision to torture him and whip him for the prostitutes' lies as well could easily be interpreted as racially motivated - since he doesn't show such harsh treatment towards any of the white characters.
  • And You Thought It Would Fail: It took Clint Eastwood several years to actually get around to reading the script, as his script reader had initially told him that it wasn't very good.
  • Badass Decay: Munny went from a fearsome cold-blooded gunslinger to an old pig farmer who can't hit anything with his revolver and struggles to even mount his horse. He eventually recovers his old form after Little Bill kills Ned, and he consumes a bottle of whiskey.
  • Designated Villain:
    • Davey, as mentioned below on Disproportionate Retribution on the main page. He's treated as being equally guilty as Quick Mike and is targeted for death along with him trying to stop Mike half way through the attack and making a genuine apology and gift to the prostitutes besides what he was ordered to pay Skinny.
    • Little Bill's deputies. To Munny, they're just Mooks of his nemesis but they seem like friendly guys just following the orders of the elected law enforcement official while trying to keep the peace. They aren't said to have directly participated in Ned's death. Clyde even seems like he might have favored a harsher punishment for Quick Mike and Davey at the beginning.
  • Hilarious in Hindsight:
  • Magnificent Bastard: William Munny is a retired, monstrous gunslinger who once terrorized and haunted the old west with his vicious nature. Though settling down as a farmer for years following his wife's death, Will goes out for one last hurrah to take down two cowboys who beat brothel women. Working with his old partner Ned and the Schofield Kid, Will overcomes his initial rusty skillset to ambush and kill off the trio's targets with clever tactics. After Ned is captured and beaten to death by the brutish Little Bill, Will lets his inner beast loose as he marches into a crowd of Bill's allies, kills half a dozen men with his spectacular gunfighting, and executes Little Bill. Will then terrifies the rest of the town into respectfully burying Ned's body and never again harming any working women, threatening to "come back and kill every one of you sons of bitches" before ending his violent ways forever, disappearing from public eye and becoming a propserous shop owner with his beloved children.
  • Moe: Delilah. She's the cutest and most innocent of the prostitutes, and even her horrific injuries can't quite take that away. She also cries a lot.
  • Moral Event Horizon: Bill was no saint to begin with, but he crosses the line when he tortures Ned to death. Munny thinks he crossed it a long time ago, and some of his past evils are mentioned, but in the film he remains at worst a pretty dark Anti-Hero.
  • Retroactive Recognition:
  • The Woobie: Delilah. When William Munny is trying to tell her she's still beautiful with scars while not betraying his late wife, you just feel so much for both of them.

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