despite the clunky interfaces i had not much trouble replaying fallout 1 & 2 recently (1997-98). I've also often replayed Master of Orion 2 (1996) and SimCity 3000 (1999).

And if you're willing to go with simpler games Pac-man (1980) and tetris (1984) both still hold up, as does Arkanoid (1986).