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Diogo said:
For 1999 it has to be Silent Hill. That game was really.... something.

For 2001 I'd say Silent Hill 2, because of Pyramid Head.

Here are some more old-school scary games.

System Shock (1994)

Clock Tower (1995)

Resident Evil (1996)

Blood (1997)

Resident Evil 2 (1998)

Some days I just blow up.