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badgenome said:
Pool of Radiance or something. Thankfully I outgrew PC gaming and now play on consoles like a real man.

I read those books.  I remember absolutely none of it.

On topic, the answer is probably Daggerfall.  It was an experience that felt way more mature than what was on consoles at the time.  Sure, the graphics were so bad that I would get a splitting headache, to the point where I would feel physically sick, but it was basically the same game as Skyrim.  I'm not even kidding.  Actually, the atmosphere of it felt a lot more wicked, like it was inviting me to be a cut-throat rather than a hero.  I still remember seeing one of the topless dancers in the thieve's guild for the first time.  It really had a very sinful vibe.

I also remember my sister laughing at me for dying to the very first monster, a giant rat.  Not my fault, I just wasn't used to the m/kb combat style.  Shut up.

Ragnarok Online is what got me into MMO land, though, and then the launch of WoW resulted in my first purchase of a "gaming" PC.