Silent Hill

Probably Silent Hill. That game scared the crap out of me.

Silent Hill 2. Basically your character is a sexually repressed murderer, shown bits and pieces of his subconscious desire and wasted life by his own physically manifested will for punishment; Silent Hill's executioner from the 1800's, Pyramid Head, running around raping monsters. He goes through all these ordeals to discover himself and why his wife died, which he killed her himself, and even while discovering the truth, he uses one lesser regression to hide it...it's depressing. In one of the ending he ends up committing suicide. :/ There's also a young women who was mistreated by her father, and is in Silent Hill to witness her suppressed rage...everyone who goes to Silent Hill sees something different. While the protagonist, James, is lonely and is attacked by monsters, the women feels really hot because she set her house on fire killing herself and her dad, and is basically stuck in Limbo until she releases all her rage and hatred, (Which she fails to do, and her conclusion is that she was consumed by her own emotions, shown through a house fire in which she willingly steps into.) and when a monster jumps up on her and attacks, she screams for her "daddy" to stop. I was like wut...*Shivers* Then you beat up the monster and save her, but she thinks you're beating up her dad...ugh. Nothing is ever direct in this, you have to try and interpret the symbolism, and even if it wasn't for that, the monster design is messed up, the town is very well made, it's scary and often lonely, and you're always on edge and anxious. It's a fantastic game. Most of them are scary, but SH2, so far, (Though Pyramid Head is supposed to be the returning Chupacabra, I don't get it, but he's in 5, too.) is the odd one out, and my favourite. It's the most well done, with a story that seemingly stands apart from the other games, and is goddamn scary. Though, in Silent Hill Origins, seeing "bang me my son" written in blood in the women's shower at that asylum is no less creepy. Runner up for most disturbing game has to be Manhunt, for obvious reasons. :/