If you aren't familiar with Silent Hill 2 or the work of Akira Yamaoka, you should correct this grievous error and acquire this game immediately. If that's not an option, or you have already, then feel free to read on.
 
Recently, I've become obsessed with the Silent Hill soundtracks, from the very first game's opening theme to Silent Hill: Homecoming. Quite simply, these are some of the finest game soundtracks ever recorded, and well-worth checking out even if you dislike the thought of playing a survival-horror game. The variety of styles is stunning: mournful yet uplifting rock guitar noodling, chilling industrial noise, more classical pieces, ambient electronica, metal, etc. I wish I had more of knowledge of composition to comment in detail on Yamaoka's work but really all that matters is it complements the twisted duality of the Silent Hill universe wonderfully. Like the very best game soundtracks it gives me a nostalgic feeling that makes me wish I could re-experience the game all over again.
Silent Hill 2's OST is probably my favourite so far. What would you say are your own favourite Silent Hill tracks or musical moments? 
For SH2 I recommend 'White Noiz', 'Overdose Delusion', 'True', 'Promise', 'Love Psalm' besides those linked below. Listing every track I think is great is too big a task for one blog alone.
 
 

Definitely one of the best game soundtracks of all time, from beginning to end. Here's my ranking, for what it's worth:
 

• Silent Hill 2
• Silent Hill 3
• Silent Hill 4
• Shattered Memories
• Homecoming
• Silent Hill 1
• Origins
  

Breeze in a Monochrome Night is my favourite work by him.

The vocal tracks on Shattered Memories and Homecoming are the best thing about those albums. They're super good. The vocal tracks on 3 and 4... not so much. :) I think Yamaoka was still learning.

As great as the soundtrack for Silent Hill 2 is, I have to say that Akira Yamaoka's work for Silent Hill: Origins totally knocks it out of the park.

I had SH3 circulating in my car collection for a while. Good music music, not "good for a game" music.

I have never played a Silent Hill game in my life, perhaps I may have played some demo's of the sixth generation version's, but recently I bought Silent Hill 2 (Special Edition) on Ebay for PS2. I was really looking forward to play it and was in the mood for 'horror' things, typically I dont enjoy horror but I have a short spell where I wanted to try out Horror films/games etc., but it took so long to arrive I had lost my great urge to play it. I keep seeing it in my collection, the 'special edition' box makes it stick out, and meaning to play it eventually but people talk about it in such an amazing way that I feel I should designate a reasonable chunk of time and devote myself to giving it a proper try.