For me it would have to be the part in Imprint when one of the geisha's is getting tortured by everyone else and gets 18" long hair pins stuck under all her finger nails and gets her mouth pinned open with six of the hair pins. All while being suspended at weird angles from the ceiling.
I play through once and stick to the story, then I go through again to get every trophy I can. I think trophies/achievables are good, they help prove to people that you have done some of the harder things on the game.
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