I was proud of myself to finally go back to the original Deus Ex for the first time just a few months back, which held up fairly well despite the aggressively aged parts of it.
But my biggest shame is Planescape Torment. I love the heck out of Baldur's Gate and the other infinity engine games, but I never know this similarly styled game even existed until last year. I picked it up on GOG but.. I have a hard time playing it. It just aged a bit too much for me and I can't handle the janky UI and movement. I even modded it (with most of the GOG recommended mods), but it wasn't enough. I do intend to go back to it.. but it's a hard sell for me.
Thief 2 is a similar situation. I bought it just a couple months ago.. but same thing. Can't push myself through it. The game doesn't give me enough information to handle it's complexities in the way a modern game would. Though this might be solved by reading the manual, this was made in that period where one actually mattered. It was just a bit overwhelming to me.
Heavy Rain is on also my shame list, I really aught to play it before I accidentally get spoiled someday. I just don't have the motivation for whatever reason.
And just as a general note, with some exceptions I missed a whole giant section of PC gaming back when I was younger, when things like Counterstrike, Quake, UT, and Half-life were huge. I missed out on that entire scene and you can never really go back to that era again (I did eventually get around to playing Half-life 1 just a couple years back at least).
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