18Feb/100
Winter Olympic Edition: SkiFree

Easily one of the greatest advances in computing achieved in the 20th Century, Ski Free (part of the totally awesome Windows Entertainment Pack that shipped with many family computers in the early 1990s) catapulted users into a pristine world of glistening snow, drunken purple ski bunnys, and ferociously hungry monsters. Probably the only Skiing game anyone has ever played, Ski Free is probably better than any of those newfangled snowboarding video games with their fancy polygons.
Missing your 16-bit skiing? Chris Pirih, the Microsoft Programmer who authored Ski Free, has recompiled the program to run under 32-bit and 64-bit operating systems. I'm running Windows 7 64-bit, and the slopes are in great shape. Get it here.