Just curious what the oldest game is that you’ve played, and whether you enjoyed it or not. I’m less interested in the technical experience, so you can use the original release date, even if you played a more modern implementation.
For me, Fate/stay night just barely beats Clannad, by a few months. Both were released in 2004, and both show their age a little bit (Clannad in its convoluted branching, Fate in its resolution options), but are perfectly playable. But of course both are super popular classics, so I wonder if you all had similar experiences with more obscure or older titles.
I’m in the process of playing Higurashi, released in 2002, and it’s good. It’s a very different experience from the anime. I actually played the Umineko VN first, which became my favorite thing in any medium quite quickly. Higurashi just keeps getting releases, re-releases, new adaptations; the train keeps going. The original release had very amateur art, but modern console releases in the Higurashi franchise have polished opening movies, redrawn sprites and full voice acting.
This certainly isn’t an obscure title, of course. Higurashi doesn’t offer you any choices, and it plays out just like a novel with no branches. Personally, I prefer kinetic visual novels like Higurashi and Umineko, but I know many don’t share this opinion.
And I suppose I’ve played Subarashiki Hibi, too, which is a 2011 remake/re-imagining of Tsui no Sora from 1998, which I really liked. I don’t really count that one on account of Subahibi being a completely different game.