Silent Hill is an interesting series because there's pretty much always been someone different leading the project from one game to the next. The only guy that's really had a hand in everything SH has been Akira Yamaoka, who does the music and sound, and it's this area where the franchise displays the most continuity across sequels. Of course, now that he's gone, I dread to discover what any future SH game will sound like...he always did a fantastic job.
But it's conceivable you could play SH2, love it, and hate everything else. SH2 really has a very distinctive vibe when compared to the rest of the games. It's my personal favorite because I feel it strikes much harder on a human level and can be quite deep with its symbolism...so much so that I've spent hours discussing it with friends. I like the rest of the games, but for me SH2 is the pinnacle. Then I'd say my second favorite was 4...i just really liked the Room concept, but I recognize a lot of people consider this entry the black sheep. SH1 and 3 are quite good, but 3 is more of an explanation of SH1, so if you intend to play it, play 1 first or else you won't get as much out of it. And quite frankly SH1 needs SH3 because thanks to the horrible translation and censorship that went into SH1, SH1 can be borderline incomprehensible at times. Can't beat the atmosphere, though.
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