Kudos to Andrew Tait, who created a virtual machine and used it to install every version of windows*, and then used it to upgrade to the next version. Even better, he screen captured the entire process, and presented it with commentary. This one is just silly geek fun, with the only science fiction aspect being the use of the Doom II game engine to test compatibility from OS to OS.
*: Or at least every version he could find that could be upgraded in sequence. He skipped ME because it could not upgrade to 2000, but only to XP. I agree with his decision, because out of the two OS’s 2000 was real, and ME was a brutal mistake that even Microsoft abandoned as soon as they were able to do so.