I recently played knights of the old republic several months ago and it still holds up today as the best single player star wars RPG Ive played (not that there are many of those out there). Before skyrim came out I played a bit of Morrowind too.
The one game that I play a lot though is X-Com which is just a fantastic game that I have a ton of fun with. I love being able to run a global anti-alien invasion force and place my bases anywhere as well as getting the equipment of my choice in each base and to each soldier. I can shoot down UFO's, raid landed UFO's, invade alien bases, and even have my own custom base invaded. No playthrough is the same and its just a fantastic game that I can never put down for long
Baldurs Gate 1 & 2 (always liked BioWare RPG's)
Age of Empires 1 & 2 (Even though i'm terrible at rts games)
Some of the older C & C games
Rome: Total War (Thats old right)
Mostly NES and Genesis games, such as Ninja Gaiden, Final Mission aka S.C.A.T. (but a bit more hardcore), Streets of Rage (the Spanish stew of a remake for PC is pretty awesome), Mutant Chronicles Doom Troopers (YAY!), Strike series etc.
As for DOSBox-legged old farts, can't get Blood running properly. And I wonder if Space Quest will run at all.
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