
Forgive my basic bitchdom, but this is an always has, always will be scenario.
Alone in the Town
An unorthodox pick. I imagine most people go for Theme of Laura, Promise or White Noiz, though for me it's always been this tune. It marries many of the things that I enjoy most about the SH2 soundtrack. The muffled, washed-out sound. The mist-like ambience. The fantastic percussion. It also has a pleasing intro, which makes it easy for me to fall into the atmosphere of this song and has persisted throughout my memory as a result. The song also reminds me a great deal of "Endtroducing" by DJ Shadow, which is the reigning king of "nocturnal" music - a make of album that the SH2 soundtrack also belongs to.
I'm an optimist and greatly prefer the good ending of SH2 over the sadsack bad ending, which also plays into my bias. The music has a perseverant quality that I think fits with James' character arc. The song also plays at around the mid-point of the game, which enhances the feeling of moving forward and having too much to lose.
Honourable mention goes out to the Ernest Baldwin theme in the Born From a Wish side story - the second song that comes to mind whenever I think about this game. Being my favourite game ever, I never wanted the Silent Hill 2 ride to end. Yet, through all of the time that I've spent thinking about this game I've become acutely aware of the fact that there's nothing waiting for me beyond the confines of this self-contained story. The snippet of James' life that I got to see isn't enough for me to really make a judgement on his fate or character and there's nothing to go back to once the story is over. The town is empty, yet I'm still here.
It also helps that the Born From a Wish story is just a really good part of the game. It answers zero questions and doesn't mean anything in the grand scheme of things, yet it still manages to leave me with a lot to think about. It isn't the scariest part of the series, though it's easily the "eeriest" with how it establishes a lingering distrust and doesn't do anything to assuage that sense of dread.