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  • Alas, Poor Scrappy: Steve the Drunk's big mouth was determined to tempt Karma, but boy, what happened to him in the end was nasty.
  • Badass Decay: Averted; Al Swearengen grows more sympathetic and helpful over the seasons, but one scene seems to be explicitly written to remind the viewer what a sadistic bastard he can be: Swearengen has one of Hearst's mooks at his mercy and delivers a speech of righteous indignation over the mook's crimes, then admits that he's really just torturing the mook for the fun of it, and would himself kill women and children without hesitation.
  • Complete Monster:
    • George Hearst, who is willing to crush anything that stands in his way, believing that he "talks to the earth" and answers to a higher authority than mere humanity.
    • Francis Wolcott is close, being a somewhat Ax Crazy serial killer, but he realizes what an evil troll he is and criticizes himself on a number of occasions.
    • Then there's Lee, also in the Hearst organization, who thinks nothing of using women in forced prostitution, giving them little food and no medical care, then tossing their bodies in a fire when they inevitably die.
    • Al Swearengen should be this, but because of Ian McShane's brilliant performance, and because of hints of a Pet the Dog side, he comes across as a Magnificent Bastard, even when plotting a hit on a little girl.
    • Cy Tolliver looks at first like a "good" counterpart to Al, acting like a father figure to Joanie, paying Doc to visit his hookers three times a week (instead of each few months like Al)... and then he has a couple of bit-time teen thiefs beaten, shot (one of them by forcing Joanie to do it) and fed to Wu's pigs. Both Joanie and Eddie see this as Cy's Moral Event Horizon.
  • Creator's Pet: The theatre troupe in general in the third season and Jack Langrishe in particular.
  • Crosses the Line Twice: Mr. Wu goes to Al's office to demand (in his broken and extremely limited English) that he do something against his rival, Mr. Lee. Al says that he will meet him "to see how much juice [Lee]'s got behind him". Wu is confused and asks "Jews?" while mimicking a bunch of coins in his hands. Al negates. Wu gets up from his seat then, moves to the window, points to Sol Star's shop, pretends to have a big nose, and asks again: "Jews?"
  • Freud Was Right: Many character's personalities could be explained by their upbringing and parental influences (or lack thereof).
    • Al was beaten regularly as a child (the beating he received because of the death of his epileptic younger brother would explain both his sympathy to the Reverend Smith and his aversion to William's funeral) and was sold to an orphanage run by a woman who turned out to be pimping the children in her care. His opening of the Gem and hiring of girls from that same orphanage is a twisted way of protecting them, the same way Trixie mentions Al being protective the same way about Jewel.
    • Joanie Stubbs and her sister were sexually abused by their father before being sold to Cy, which made Joanie extremely protective of women in similar situations. Joanie recognizes a similar pattern of childhood sexual abuse in Wolcott as the reason for his extremely disturbed sexual tendencies.
    • Similarly Jane being abused by her father would explain her terror of Al as he confronts her in the Doc's office, as well as her extreme attachment to Wild Bill as a substitute father figure.
    • Word of God is that Seth's anger against injustice comes from his being regularly beaten by his father. Which is also the reason he ran away from home when he was younger.
    • Contrast this to more 'normal' and well adjusted characters like Sol who seems to have had a good relationship with his father.
  • Magnificent Bastard: Al Swearengen slowly earns this title over the course of the second season when it becomes clear he's trying to bring order to the horrible frontier town in order to protect his dominance. Sure he orders hits on little girls, kills innocent people and generally does horrible things to everyone, he's practically a populist man of the people compared to Hearst and his cronies.
  • Squick: The Gleet. "Mother of God" indeed. Also Doc Cochrane pushing a needle through a headwound in the first episode.
  • What an Idiot!: Flora and Miles, again.
  • The Woobie:
    • Reverend Smith. No one takes him seriously from the start, but at least he has God - then it's suggested that his intense feeling of being loved by God is a symptom of the brain tumour that's causing his fits. Then his body starts falling apart and he starts to hallucinate.
    • Alma Garret for her Cartwright Curse.
    • Whitney Ellsworth.
    • Joanie. First Cy makes her shoot a young girl on the face, then her attempt to start her own business far from him is ruined by a Serial Killer.
  • Unfortunate Implications: Dr Cochran suggests that the Reverend's religious conviction is based on a tumour screwing with his brain chemistry, and his progression from that point certainly seems to back this up, unless it's a self-fulfilling prophecy.
    • Nothing unfortunate about that. It's a medical fact that a brain tumour can cause sensations similar to a religious experience.
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