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[Neonivek]

The first Silent Hill (for the PS1). The voice acting was kinda bad, but I still found it to be the scariest thing I've ever played (and I played it years after it was released, on an emulator).

2 is also great I hear.

[Flying Dice]

Sniper: Ghost Warrior was pretty horrifying.

That game was horrifying. *sob* How can you be so broken? *sob* NO! Not the stealth mechanics! NOOOOO-

Getting shot from two miles away through heavy concealment by an AI with a pistol was only cool when Far Cry did it.

/hipsterglasses

The first Silent Hill (for the PS1). The voice acting was kinda bad, but I still found it to be the scariest thing I've ever played (and I played it years after it was released, on an emulator).

2 is also great I hear.

Yeah, 2 is supposed to be one of the best in the series.

[Astral]

Superman 64 will cause you to never sleep again.

Nightmare House 2 has a few good moments, but you need Half Life 2: Episode 2 in order to run it.

[ukulele]

If im not mistaken the first penumbra was kind of a tech demo, was free and gave you a taste of the saga, ill recomend u download that and if you like it buy some of the actual games, all are recomended and should be fairly cheap by now.

[Neonivek]

Superman 64 will cause you to never sleep again.

Goodness if your going to list that you might as well list Illbleed (which... no one can get anymore...). I will say ONE level out of all I consider to be the most disturbing.

[Anvilfolk]

There's always System Shock 2 - might be considered abandonware by now!

[Neonivek]

There's always System Shock 2 - might be considered abandonware by now!

Given its creator... I doubt it.

Going to put Darkseed into the ring. Though the largest issue with the game is you probably will need a walkthrough just to beat it.

[kg333]

Chzo series (free)

Bump for the Chzo mythos.  It's old school point and click adventure horror, and quite good.

Amnesia is the current standard for first person style horror, although your mileage may vary. 

System Shock 2 is very good if you can find a copy, although not entirely scary.

KG

[Bouchart]

Doom 3 has its moments.

[Pakhawaj]

Alone in the Dark is on Great Old Games for $6, and remains surprisingly scary despite its age. It's from the era of weird 3d graphics that have about ten polygons per model, but that really only enhances the surreal creepiness. I would never want to see anything that looked even remotely like the main character models in real life.

It has a bit of a flaw in that you kind of need to keep an FAQ open to avoid cheap instadeaths and know what anything is. It's possible I'm just dumb, but I would have had no idea that mirror beats gargoyle (I think it was a mirror?) otherwise.

Yeah, the purple dog monster particularly freaks me out, I've no idea what that thing is supposed to be.
You must have played the game when the internet was a widespread thing then I guess? Internet FAQs dull the senses methinks! There were enough clues for the puzzles for kiddie me, the library in the attic has the clue to the gargoyle puzzle in one of the books (to be fair, I remember this because I struggled with those things too).

I've just remembered a spooky horror game from the Adventure Game Studios called "The Marionette", the pacing is a little strange at times but it's scary nonetheless. There are some other horror games on that website and they're all free, I can't remember if there's anything as scary as The Marionette though.

[Rakonas]

Chzo series (free)

Bump for the Chzo mythos.  It's old school point and click adventure horror, and quite good.

Thirded

[Elfeater]

Call of Cthulu is pretty terrifying later on, in a creepy sorta way. Not sure if thats the whole title.

[Hawkfrost]

Call of Cthulu is pretty terrifying later on, in a creepy sorta way. Not sure if thats the whole title.

Call of Cthulhu: Dark Corners of The Earth?

There was an NES game called Sweet Home that was released only in Japan.  It's an RPG and precursor to Resident Evil.  Might not be horror, but it's creepy.

Well, I would say it's horror, but not in the modern sense.
It doesn't try to jump out and scare you or anything, but some of the enemies are pretty grotesque and it deals with a rather morbid story.

System Shock 2 is very good if you can find a copy, although not entirely scary.

Not scary? I guess you are made of sterner stuff than I.
I don't think I've tried playing since the last time when I was looting a corpse and an enemy snuck up and whispered in my ear.
Fell off my chair and quit the game.

[Pakhawaj]

Just remembered again! The Haunted House sequence in Vampire: The Masquerade, the game itself isn't entirely scary (though there are some other frightening moments) but that whole level was the most frightening thing I've experienced in a computer game, I literally could not play that by myself, I had my girlfriend at the time play through certain parts for me, haha.

[Elfeater]

Yes hawk that's it thanks