I found this video showing an experiment. This guy started with DOS 5.0, a clean and empty VMWare instance and spent a whole day installing every single MS operating system until Windows 7!
Something impressive is that the games installed in DOS still worked! ( they broke in windows 2000, but got back in XP) that is almost 25 years of compatibility! pretty impressive MS really! while watching the video I remembered all those days when loading DOS from a 5 1/4 disks was a real pain!
It is a nice video if you want to remember those days. I wonder if some did something similar with any Linux distribution.
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