The first scary game I played was the first Resident Evil. I remember that game used to make me jump right out of my seat. Silent Hill was pretty creepy too. I got a thicker skin over the years and it takes a lot to scare me now. But I'd have to say Silent Hill The Room is my choice for scariest. It really left a dent in my sanity lol. It's one of those games that really stuck in my mind, and it really makes you think after you complete it.
Silent Hill 2 is probably the scariest video game that I have ever played not because it is scary in a traditional sense or because it makes people jump out of their seats in fear but because of its psychological approach to fear and despair (this is very effective). Silent Hill 2 does something that I haven’t seen very many other video games even attempt. With that being said, I have also played Silent Hill 4: The Room. This video game has such an oppressive and unsettling atmosphere. It is definitely one of my favorite survival/psychological horror video games.
Silent Hill 2 I also tend to think back on when pointing out the terrific psychological horror approach that the game takes. The first Silent Hill is great too, when thinking back on that encounter you have at the shut doorway. I'll just leave this can of beef unspoiled. Silent Hill 2 though has many of its own fantastic moments. From a disturbing stalker-like entity to the creatures that shock in a bevy of ways.
Silent Hill 2 affected me emotionally. But it didn't really scare me that much. Another game I forgot to mention that I thought was scary was Clock Tower. I always jumped out of my seat whenever Scissorman would make a surprise attack. My heart would start racing too whenever I heard the creepy music playing when he was near, and then hearing those giant scissors open and close repeatedly as he was coming closer.
The alleyway with mutant children towards the beginnging of Silent Hill 1 did it for me. I don't play scary games anymore because of that.