I can't remember the details, but there were some levels in the Aliens .wad for the original Doom that I literally could not play alone late at night. Hell, forget the levels - it was the whole game with that patch.
And I'm sure I'll catch hell for this from Clix, but there were some downright terrifying moments in RE4, particularly during the storm and in the later chapters.
The first time I played Silent Hill 2, the outside and first hotel were fairly creepy. The location that scared me the most was a certain bathroom/locker room...
[21:14] pixelman: I blame fheblackdragon
[21:15] pixelman: That's not an f by the way, it's a fancy t.
[21:15] Objection: Tales of Graces "fancy t"
[21:15] Objection: Tinal Tantasy
[21:15] theblackdragon: lol OB
[21:15] pixelman: OB knows what he's asking about.
The hospital in Silent Hill 2, or, as Vendetta noted, the stretch in RE4 just after night falls.
The hospital in SH2 scared me and sticks out in my mind as one of the scariest video game locations. I'm a chicken when it comes to video games, like brutus, as well though. Horror movies don't bother me at all, but video games scare me to death.
twilight town in paper mario: the thousand year door. the music is so freaky... especially when the bell rings, your always scared hat it may be you even though you know its not...
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Topic: The Scariest Game Location Ever
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