An obvious one but Championship Manager for aging well... Principally because it's barely changed since dot to the present day. Of course, people will always play the more recent incarnation but you could always go back to an older version and slip straight into it without any problems. Same for the Civ games, you can go back to the early ones and graphical progress means squat, they have the same core and all can still be played to death. We'll go for the latest incarnation but you can go back and still have a bally good time.
Those that haven't aged well... Hard to think of anything in my collection, a lot of the ones I think of were pretty crap to begin with but got a few hours because they were there. A few of the earlier 3D graphic based games to me, the graphics didn't age well and colision detection was shite. That said you still get that plenty in lesser games now...