Linked by David Adams on Thu 3rd Mar 2011 04:08 UTC
Windows If you had asked me, I would have guessed that this wouldn't be possible. One intrepid OS explorer has made a video wherein he not only installs every version of Windows since 1985's Windows 1.0, but proceeds to upgrade from one to another. The video, titled Chain of Fools: an Exploration of Windows upgrade procedures, shows how DOS and Windows are installed in a VMWare VM, and how a couple of DOS games were installed to see how newer versions of Windows handle backward compatibility. Similarly, various customizations were made to the Windows preferences to see how they survived the upgrades. Video embedded after the break.
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A fun video, thanks for posting it.

I don't think one can really draw any conclusions from it regarding applications compatibility and display settings. After all, due to hardware incompatibilities and the system requirements of different Windows versions, the upgrade sequence shown here could not really occur in real life. It could only be implemented using a virtual machine environment -- which didn't become widely available until several years ago.

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