... based on modification date?

Other than a few with corrupt date flags (1903), my oldest is

"Backgammon Freeware" by SoloSoft. Date modified: Nov 27 1984

And.... after all these years it still works!

Maybe I should mail in my donation?

Dunno, at home probably nothing older than maybe a year. I seem to go through harddrives like crazy. They don't die I just see ones on sale or more space and end up buying them. Probably got 3-4 40gigs-120gig laying around that aren't being used and lord knows what is on them.

The oldest game I have on disk though would be Secret Weapons of the Luftwaffe from lucasart. :( Miss that game.

It is a wood rasp that belonged to my great grandfather. Oopps, wrong type of file. :D