Here are my personal "top 5" horror games: the ones I had a hard time playing through at times. I've played most survival horror titles, but something about these made it difficult to play with the lights off. I'd recommend all of them, and quite a few more. But for all these games, the lights do need to stay off, and it's better to play late at night. Silent Hill tops the list, if only because the imagery in the games gives serious nightmares...I love it.
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My favorite Survival Horror game. If you haven't played it, DO IT! Basically, the feelings of loneliness and dilapidated environments create a seriously creepy space. This game messes with you.
Basically a plot retread of SH1, but it takes all the elements of SH2 and makes a very, very, unsettling game. It's the sort of thing you can only play in short bursts.
Ok, this should be the REmake for GameCube. The REmake is by far the scariest in the series, and also quite difficult if you've not played the others. Playing as Chris is the way to go, with only 6 item slots you're never going to feel confident.
A unique horror game, where the enemies are freaky Japanese Ghosts (think, "the ring" or "the grudge") and the subject matter is extremely macabre. The sounds and feel add a lot of jump scares and a strong sense of unease
An overlooked horror game, this one is surprising given the action/fps nature of the game. But by time you get to the end, it gets quite unsettling. There's a certain degree of sadism and creepiness that add to the dread. Play this one in 5.1 though, because the sound design is amazing.