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Basically every song in the entire Silent Hill series deserve a spot on this list. Just search up "Silent Hill OST" on youtube. Or you could just find some convenient playlists on "stripedlady's channel."
Credits where they're (usually) due: Akira Yamaoka — composer, Joe Romersa — arranger, Mary Elizabeth McGlynn — vocals
As of Silent Hill: Downpour, Akira Yamaoka has been (sadly for most Silent Hill fans) replaced by Daniel Licht, better known as the composer for the Showtime series Dexter.
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Silent Hill 1
Not Tomorrow, the song that plays during Lisa's reveal in the first game. It's just so haunting and melancholy.
"Esperadote", the theme song to the worst ending in the first game. It's a downright gorgeous, operatic theme, sex to your ears. Unusually for a Silent Hill game, the lyrics are in Spanish.
The song in the opening of Silent Hill 3, End of Small Sanctuary. If you listen to it, watch the scenes for it too. Sadly, within the game, it only plays while you're in the alleyway outside the mall at the very beginning.