ANSWERS: 4
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Postal
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Probably Silent Hill. It's very subtle, but also quite definite-most of its plot pillars center around sexual abuse and torture. Good thing everyone over at the ESRB are a buncha morons, or that series never woulda saw the light of day in America.
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http://www.addictinggames.com/interactivebuddy.html It's not bloody, but it's sick in a way I didn't expect when I first saw it.
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First things that come to mind are Manhunt and the Silent Hill series. The Grand Theft Auto Series is also fairly "twisted" (though a hell of a lot of fun).
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