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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/
pleasant surprise to see 2 of my favorite games on the list (sanitarium and phantasmagoria).
Only finding out after getting Half Life 2 you will need to install something called Steam and download more data.
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TentacleMayor: 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.
depends entirely on your mood (and honestly - age :) when you play the game

I really loved Phantasmagoria's slow creep crawling all over me the more I played... it's not in top 10 of my adventure games, but it's there in my top 10 of most atmospheric experiences

clearly subjective though!
I would add something from Alone in the Dark myself. I'm not sure which is the scariest moment in the game because it is creepy through and through, but I can't say any other game I ever played made me feel as uneasy as it did.
Here's one for the old kids at heart:

TAPE LOAD ERROR.

Say goodbye to another 3-10 minutes.
The first Thief game had some pretty spooky moments, with the skeletons and their sinister laughing. System Shock 2 also had some creepy audio logs, and those monkeys and the cyborg midwife that creeped me out.
To be in the darkness, surrounded by dummies in an gloomy supermarket in Condemned Criminal Origins was a true jumpscare moment for me ! This game deserves a GOG release, curse you SEGA !
Post edited October 31, 2019 by MaxFulvus
Renfield bursting into the room in Dracula in London, or the end of SkiFree when the Abominable Snow Monster starts chasing you.
Oh yeah, can't forget the Cradle from Thief 3. Doing that level not knowing what to expect (because it hadn't been hyped yet) was amazing. Scary, but amazing.
Entering the Asylum levels in Shadow Man.
Thief the Dark Project - Down In The Bonehoard level

A favorite of mine with great atmosphere, Thief is the first game, where I felt being inside the game.

This is the level with the undead in catacombs, and if you play it in the dark just the sound itself will give you creeps.
How is "Outlast" a classic PC game?

Anyway I would add "I Have No Mouth And I Must Scream", some of the levels are truly scary, I especially remember the one with Ellen as very disturbing.
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Ingsoc85: How is "Outlast" a classic PC game?
How far back are you drawing a line on what constitutes a classic? If we're putting Outlast up on the block, then DCotE might as well slide up there with it.

Also, I didn't say it in my previous response but what I'm absolutely glad to not see on GOG's list is Amnesia. Thank you, minions of GOG who were probably underpaid to compile together this list a day ago on short notice.
Post edited October 31, 2019 by TheMonkofDestiny
I recall certain cinematics from Starcraft... They really set the "we're doomed" mood.
Disclaimer: I don't really enjoy the horror genre so my "scary" memories will have a very peculiar mood.

I remember being scared as a kid of the Scabb Island cemetery from Monkey Island 2. Such a spooky atmosphere. The music had something to do too. Even nowadays I still feel a knot down my stomach when I visit that location.

(To a lesser extent, the cannibal village at Monkey Island made me a little nervous... but Lemonhead and co. were so fun I couldn't resist going back).