I played Silent Hill 1 back in April and thought it was pretty great. Dated, but still excellent at crafting an atmosphere and a sense of not being safe in this cozy little town. I'm really glad I played it just before it got a remake announced, it means that when I do play both of these things I'll be able to compare my experiences directly as a relatively new fan.
I just started SH2 the other day (the PC enhanced edition! remakes go home!) and so far it seems great, though admittedly I'm still right at the start. I'm in the unfortunate position of having to play a bunch of Sonic Chronicles: The Dark Brotherhood right now for future episodes of my podcast, and that game is both long and ingratiating to play.
Previously, I've also played the Silent Hill-inspired SIGNALIS, and that is one of my favorite fucking games ever made. Holy shit you guys have to play Signalis. It's scary, it's a visual feast for the senses, there's classical Lovecraftian influence (none of that 'just drop cthulhu in there' shit), the weapons feel like they picked all their favorites from different Resident Evil games, the puzzles made me think really hard but not a single one required a guide, and there are robot lesbians. How could you not like it! It's got robot lesbians!
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