Do you have buckets of free time and love antiquated Microsoft operating systems? You might want to give this guy a call.
Youtube user TheRasteri (Andrew Tait) posted a 10 minute video of his Windows OS experiment. Using VMWare, this video tracks the installation of DOS 5.0 to Windows 1.0, and then every additional upgrade. Tait's intent was to determine how compatible with each other the various versions of Windows were, and tested this using color settings and programs installed in DOS at the beginning of the video. Based on the download times of each of often mammoth-sized updates, this experiment looks to have taken Tait at least a day to complete.
Turns out that in some instances Windows offers over 20 years of compatibility. Sadly, the fast-food restaurant color scheme that Tait chose and Doom II only lasted until Windows 2000. Strangely enough, Doom II came back in XP, but the color settings were still gone (even when Tait reset them in Windows 2000).
Best part of this clip is the sudden impulse and affinity for the LucasArts Game "Monkey Island"- it's damn near irresistible.
Final thought: if Microsoft can boast 20 years of compatibility, why did Tait name the clip "Chain of Fools"? Not that I disagree, mind you.