I’m not a Silent Hill conpletionist, as I’ve only played the first three games, but of those I consider SH1 the best. I think it’s the scariest, and too many people sleep on the story. I think the story in SH1 is on par with SH2. The soundtrack to SH1 is also my favourite. As the series progressed the music became less hostile and industrial and more trip-hop than I would’ve liked.
This is of course not to Denigrate the sequels. I like SH2 and SH3 a lot as well, but personally SH2 scared me the least of the trilogy. It’s still spooky, but the feeling of melancholia overpowers the horror a lot making for a different experience, whereas the third game brought back a lot of the hostility that was missing in SH2, especially in the music, and I appreciate all the stupid shit they threw in for repeat playthroughs like the Lightsabre and the sailor moon transformation.
Each one has their strength, but there’s also a weakness to if all as you progress through the trilogy and realize the somewhat formulaic gameplay loop. You go to an area, explore it and gather items to solve a puzzle as enemies stalk around, then do the puzzle and go back to the streets of Silent Hill to get to the next location. By the third game this did start to wear thin for me a bit, but they also changed the loop a bit to compensate. Either way, I think perhaps the freshness of the experience helped the first game a lot. Since I wasn’t familiar with the franchise, everything in it was new, and maybe if I started somewhere else I’d have thought that one to be the scariest.