Either Duke Nukem 3D, or Sonic 3 & Knuckles Collection. I honestly can't be bothered checking which one is older, to be honest...
It's late. That's my excuse, at least. :S
I actually have two older games installed on my computer right now, Doom 2 and Hexen II. I don't feel that the first one really counts since I only play through ZDoom and while I messed around with Hexen II a bit I couldn't get back in to it so I can't say I really play it. In both cases (using ZDoom and not enjoying Hexen II) it boils down to controls - I can't go back to playing FPSs without mouselook.
Diablo 2 or StarCraft 1. I haven't played SC1 in awhile, but it is still older than D2 (Especially LoD). Been thinking about replaying as I've gone through the Wings of Liberty campaign.
X-Com gets reloaded every 3-6 months... Syndicate would be, as well, IF I COULD FIND THE BLOODY DISK AGAIN. (Sorry... minor rage twitch, there)
I load up Final Fantasy (No bloody II, IV, VII, or any other numeral) every once in a while. Sure, the story is thinner than rice paper, but having TOTAL control over the party makeup, gear, and spells makes it the best of the bunch, in my eyes.
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