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HOLY FREAKING CRAP!!!! I just watched the first part couple parts of the Real Silent Hill Experience on youtube! I thought I wasn't going to like the videos because they would analyzed the games too much, but actaully they pretty dang great! They're funny too! I recommend anybody who hasn't watched them yet, to go to youtube and watch them! They shed a lot of light on the subject!
They also backed up my thoughts about Pyramid Head. The Pyramid Heads on SH 2 are only for the punishment of James, but he wasn't the first Pyrrie (My nickname for PH... pronounced Perry). The image Pyramid Head takes on is from the executioners the were in the old Silent Hill prison. So even though the Pyrries on SH 2 were only for James, the image of PH wasn't only just for him, which kind of makes the PHs on the other games (Butcher and Bogeyman) sort of canon!
Anyway, you Silent Hill fans, go watch the videos! There's a lot of them but they're great!
Thank you, Ghostchild, for recommending them.