Quake 3 Arena. Or more specifically OpenArena + baseq3 and other mods like ratmod. Most fun I have had playing a game ever.
RetroGaming
Vintage gaming community.
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Silent Hill 2
I've replayed that game so many times but the first playthrough hits different
Morrowind but it wouldn't matter because I don't have enough time to get immersed in it anymore.
Dwarf Fortress was an amazing experience the first few times when you had no idea what to expect or do. My fortress designs have become much more boring (even if efficient) since, and I'm just unable to do the sort of artistic weirdness that happened during the first games.
Probably Fallout New Vegas (if that even counts as retro yet). I've played it to death ever since it came out and can't even remember the first time I completed it.
I know this is almost a stereotypical answer, but the Witcher 3. because after that game i went and read through all the books. so if i got to re experience it would be the difference of finding siri after 100 hours of gameplay and finding siri after 5000 hours of story. "find siri' is Geralt's primary motivation throughout the books. i can only imagine how satisfying and emotional that scene would feel for the first time with the weight of the books behind it.
tales of phantasia.
the op intro song is very memorable
If you haven't yet, play the psx version. It's gorgeous
I think this is a tie between Bloodborne and Panzer Dragoon Saga. Absolute masterpieces, both. I replay both of them at least once a year, but it would be wonderful to go back in fresh.
FF3, US version.
There was magic in that game.