For me, I'd have to go back to Civilization. For DOS.
By genre:
RTS: Dune 2. Yup, the grand-daddy of all RTSes
FPS: Unreal Tournament. I didn't get into FPS until I was in college.
SIM: Tie Fighter. I paid $50 for a joystick, Tie Fighter, and the Defender of the Empire expansion.
Adventure: Dark Castle on our Mac SE.
By genre:
RTS: Dune 2. Yup, the grand-daddy of all RTSes
FPS: Unreal Tournament. I didn't get into FPS until I was in college.
SIM: Tie Fighter. I paid $50 for a joystick, Tie Fighter, and the Defender of the Empire expansion.
Adventure: Dark Castle on our Mac SE.