In 2011, Andrew Tait of the YouTube channel TheRasteri decided to test the upgrade capabilities of Microsoft Windows by installing every major version of the operating system on a virtual machine. And now he’s back with another video that does all that plus the three additional Windows updates that have been released since 2011. But rather than just tack those updates onto the end of his previous project, he starts all the way back at the beginning to address some shortcomings in the original experiment. And along the way he squeezes in as many dick drawings as possible.
One big difference between this new “Chain Of Fools” video and the one from 2011 is that Tait begins from a different starting point. In the first video, he began with MS DOS 5.0, which was the first Microsoft operating system available as a retail product. This time around he starts with MS DOS 3.10, which was only available when purchased with a computer. From there Tait moves systematically through each upgrade, trying out various programs along the way, including Monty Python’s Complete Waste Of Time game.
When Tait conducted the experiment in 2011, it took about 12 hours to actually install all of the software (plus many more to track it all down in the first place). And Tait took to his blog to explain why he would attempt such an unusual project:
My parents have had a PC since I was about 5, so I have many nostalgic memories about early versions of MS-DOS and Windows. This is probably why I chose this project, as it gave me a chance to relive some of those memories, and finally gave me something to do with my cupboard full of old computer software.
This time around Tait reaches the ultimate conclusion that “Windows’ backwards compatibility is still unrivaled, allowing nearly 30-year-old programs to run flawlessly on brand new PCs.”