Here’s a project you might never expect someone to attempt. Andrew Tait (aka “TheRasteri“) took a fresh copy of VMWare and installed every major iteration of Microsoft’s Windows operating system from version 1.0 to Windows 7 to see how well the iterative upgrade process went. He started with a base installation of DOS 5.0 and then dug in for several hours of installation bliss. He also installed two popular DOS games, Doom and Monkey Island, to see how well they fared as the operating system beneath them ran through its 20-year evolution. You get to see the whole drawn-out process in a brief 10 minutes. As Tait says on the video, Microsoft deserves to be congratulated for the upgradeability and app compatibility maintained over two decades. Too bad these Windows upgrades haven’t all been as easy as this video shows.
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