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A revamped version of this article is here:
https://www.gog.com/blog/10-scariest-moments-in-classic-and-modern-pc-horror-games/
The scariest moment was when I realized that we're probably never going to get Resident Evil here :(
Good article.
First time a game scared me out of mine was when the giant spiders made their appearance in Tomb Raider 2
The very first Skaarj in Unreal.
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GOG.com: scariest levels in classic PC video games
1) The Ocean House Hotel in Vampire: the Masquerade - Bloodlines
2) The Shalebridge Cradle in Thief - Deadly Shadows

Some of the most memorable scary moments put together in two neck-hair-raising levels.

Edit: almost forgot:

3) The Dobermans in Resident Evil...it's "only" a jump scare, sure...but what a jump scare it was...

Edit 2:

4) The moment when you turn on the record player in Realms of the Haunting...goose bumps...oh, and the demons in the same game, when they appeared seemingly out of the blue everywhere around you.
Post edited October 31, 2019 by BreOl72
Dead Island's sewer sections. The game overall isn't particularly scary but once you hit the sewers, it's as if an entirely different person spearheaded development of that bit. Peppered with Floaters (appropriately), each time you hear their gurgled moans echo throughout the sewer tunnels it's absolutely chilling.
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GOG.com: scariest levels in classic PC video games
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BreOl72: 1) The Ocean House Hotel in Vampire: the Masquerade - Bloodlines
2) The Shalebridge Cradle in Thief - Deadly Shadows

Some of the most memorable scary moments put together in two neck-hair-raising levels.
+1 for the Cradle. No other game has ever left me terrified to move.
S.T.A.L.K.E.R. Shadows of Chernobyl is one of the scariest games around, imo. Starting from sudden rabid dog attacks in the beginning to the Brain Scorcher near the end. It isn't meant to be a horror game, but it does the job better than many appreciated games in the horror genre itself.
Post edited October 31, 2019 by Enebias
I don't know how Phantasmagoria is considered a ''horror classic''. It's poorly-paced and boring, has those 90s FMV game production values, and I think the only reasons why it was a big deal back then were the few gory scenes, plus the prestige of its creator. Get yourself Phantasmagoria 2 instead, it's not good per se as a horror game but it is a delicious sandwich of cheese and ham, pretty much the Troll 2 of horror computer games. Better yet, watch Spoony's playthrough of it. Or if you want a legitimately good 90s FMV horror game, there's Gabriel Knight 2, or Harvester for more eclectic palates.
The first pinky in Doom 3.
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TentacleMayor: Better yet, watch Spoony's playthrough of it.
There's a real scary moment in gaming... err, uh, I mean... reality. The rise and fall of Noah's relevance.
Call of Cthulhu - YES
Phantasmagoria - YES

funny that even games like Bioshock have these - when you go to a corner of a room to listen to some audiolog and pick up some items, then you turn around and you're face to face to that deformed man with the rabbit mask :D
low rated
One of the most terrifying moments, from classic Wizardry:

* You teleported into rock!

Basically, this means that, unless you remove the disk before the game can auto-save and take you back to town (or press the RESET button if you're playing the NES version on an actual NES), your entire party is gone for good (though apparently the NES version is a bit more lenient and at least provides the possibility of resurrection.

In any case, early Wizardry was quite brutal: When you have a game that, under certain circumstances, randonly deletes your characters, and that behavior is *not* a bug, you know the game is not nice to the player. There's a reason I'll only play these games with save states (though I won't use them in the middle of combat).
Facing the librarians in Metro 2033. I was ready to quit the game right there. You will remember them if you played the game.