I have seen no mention of Planescape Torment, so there you go.
RetroGaming
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Spyro the Dragon as I was back in the day. That game has always been so magical for me.
I remember loving Spyro as a kid, but I tried playing the remakes and didn't really enjoy it anymore. I wish I could experience them again as a child, not as adult me.
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.
I agree with lots of what's already been said and haven't got much to add to those extant conversations, so let me try to add in some that I've not seen:
RuneScape is a candidate. I started way back with RS Classic (the sprite-based one!).
Oh, and Dwarf Fortress too. That began in 2009.
Achaea and/or Lusternia are way up there but I don't imagine anyone but me can share the experience.
Oh, as well, Mount & Blade: Warband. Quite the adventure(s).
I don't really game anymore. But this thread did dredge up some memories, old and new.
Thank you.
Morrowind but it wouldn't matter because I don't have enough time to get immersed in it anymore.
Silent Hill 2
I've replayed that game so many times but the first playthrough hits different
Half-Life 2 and Shining in the Darkness.
Mother 3. I really don't know what else to say, this series impacted me so much in my youth and I wish I got to experience it raw.
Star Control 2
The end of the game blew my mind out of the water in a way no other twist has ever quite captured. It might have been the mental space I was in at the time too. Whatever the case, I will always remember the first time I played it.
I also wish I had played the first Golden Sun before the second, so if I could put a duology and that caveat in there? Definitely those two.