Metal Gear Solid and TLOZ Ocarina of Time. I have always been really into video games but before those two it was all fighting games and platformers for me. After those two games I understood that video games are just as much an art form as movies and music. Funny how they both came out within weeks of each other.
Undertale, but I want to go back to those times where I didn't know anything about it, not now that it's been memed to death. Playing it for the first time was such an experience back then.
Also, a boardgame: Settlers of Catan. Now I loathe the game, but back when I was being introduced to this hobby it was so good
Yes, it's a huge pain in the ass to jump in blind, even to play with guides and walkthroughs on hand. But that's exactly why!
I want to play it again for the first time. Preferably, with no knowledge of its game mechanics. Discovering its game mechanics should be either a very frustrating experience (which is my actual first-time experience with it) or a very rewarding experience depending on whether or not I actually manage to crack the code.
My actual first time with the game got ruined by the frustration, and failing that, getting the gameshark cheat codes. I still needed to get a walkthrough because there's only so much an infinite HP cheat can do in that game.