From Windows 1 to Windows 7, and everything in between, in just 10 minutes (video)
With the title 'Chain of Fools,' the video (embedded after the break) chronicles one man's attempt to upgrade Windows from one version to the next, from Windows 1 to Windows 7. The idea is to see how well Windows deals with the upgrade process -- whether settings and UI preferences are preserved -- and to see how well later versions of Windows deal with very old games (Doom 2 and The Secret of Monkey Island).
The complete upgrade process, if you're interested, is as follows:
MS-DOS 5 > Windows 1 > Windows 2 > Windows 3 > Windows 3.1 > Windows 95 > Windows 98 > Windows 98 SE > Windows 2000 (NT!!) > Windows XP SP2 > Windows Vista > Windows 7. Windows Me, may it forever burn in hell, isn't included as its upgrade is mutually exclusive with Windows 2000.
Even if you're not a fan of Windows, it's worth watching just to see footage of Windows 1 and 2, which are both quite rare. The results of the upgrade processes surprised us, too -- it's fantastic to see how many legacy applications from Windows 3 survived to Windows 7, and remained operational!