When the dogs first come through the windows in Resident Evil. They scared me once in 1998 and once again in the remake a week ago, nearly a decade later (even though I was expecting them).
Silent Hill 2 gave me the creeps, in general, that I had to stop playing it.
But scariest game moment not involing a red ring of death or lost save happened to me two nights ago when I was playing Resident Evil 4 Wii.
[spoiler] When you are in the castle playing as the blonde (I know I should know her name, I am playing the game after all) and I bumped into one of the knights in armor. Now at this point they had not started to move or anything, I was just freaked out to round a corner and bump into a knight with my left shoulder. I was already disoriented becuase I was playing as Patti or Angela or whatever her name is and did not have any weapons. Again, doesn't sound scary, but it was. [/spoiler]
Definately the two doberman's coming through the window in Resident Evil as you are walking down the hallway. Years and years ago when I was playing it for the first time, that totally caught me by surprise and made my heart skip a quick little beat.
N/A? Pop-up scares only annoy me and don't make me jump, so aside from that I don't even know what would be considered scary. I suppose the Regenerators in RE4 set a creepy mood, but I don't know if that's what you're looking for.
I still remember Resident Evil 2 on the N64, when you are walking down the hallway and the zombies grab you through the boarded up window! I was a lot younger when I got that game, but I still remember it was hard to go to sleep without a light on for a few nights!
My scariest game moment was when I was about 7, playing AD&D: Cloud Mountain on the Intellivision. Obviously it wasn't the graphics. It was the incredible silence of the game, knowing the next room you walk in could hail a loud monster that starts chasing after you. I couldn't play that game alone at night. Mind you, Alone in the Dark had me looking over my shoulder late at night as well.
The second hallucinating dream in Max Payne. Running and jumping along pathways of blood in slow-motion and low gravity in pitch blackness while blood rains around you, set to the sounds of your dead wife and child crying was downright chilling. I found myself turning the sound off for possibly the first time ever, the wail your baby makes when you fall into the darkness was just too much for me late at night.
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