Dude, even I still play the old Atari games. You can download them off the net with an emulator. Really takes you back to the days when you didn't care.
As far as replaying a game, I guess it depends on how much time I devoted to a game. For instance, SOCOM and SOCOM II are games that I played to death, and I probably won't play either of those anymore (especially since SOCOM 3 is in the system now). Final Fantasy 7 was the game I devoted the most time to (over 65 hours in the first week I had it), and I can't even think about playing it again.
However, Super Metroid (I know there aren't any more hidden items) is still fun to play every now and again. Zelda is another series that really doesn't get old and is usually always fun to play.