While doing some googling on Windows and marketshare, I ended up stumbling upon a site where they performed an experiment with almost all versions of windows. Their goal was to test the upgrade path capability of windows from Windows 1.0 to Windows 7. As seen in this video using VMWare, yes it's indeed theoretically possible to install MS-Dos 5 and Windows 1.0 and then proceed to upgrade in sequence all the way to windows 7 without needing a clean install. In fact, certain settings and folders that were created in windows 3.0 were still present in Windows 7. What ever your feelings on Windows or Microsoft in general, it's still pretty damn impressive.

http://www.youtube.com/watch?v=vPnehDhGa14

Wow, I wouldn't have thought you could even have got all those to work on the same hardware, personally. Just goes to show...

Man, that was a trip down memory lane. My dad used earlier versions of windows, and everyone in the family knew how to cd games cd doom doom

Old story is old :-P

That's newbie stuff. Wake me up when someone will try this kind of thing on a REAL machine (or I will try it, anyway) and not on a dumb VM stuff....

Ya know... ALL the machines available today, even Sandy Bridge CPU+GPU packages, are able to run in real-mode DOS :-P (if you don't want to take my words for granted just look at this neat stuff)

The tricky (and next-to-impossible) stuff would be to try to install Windows 95 (or even XP!) on these modern monsters....

Okay, neat, but I raise you Windows 3.0, good luck with that one:)

Windows 3.0? Very Easy stuff, too... it probably wouldn't go up to higher resolutions and you won't have any sound, but it should run just as well as DOS. You know, Windows 3.x is just a GUI for the underneath DOS operating system....

Yes I do know that, but it was that GUI stuff that was horribly incompatible.

I have a completely different experience about this...

That holds true for every 9x operating system ever made as well (95,98,98se,mE)

Besides I'm pretty sure legacy mode != FAT16 file system compatibility.

Bullshit :-P

The Win9x architecture is a mess, but it's far away from being a mere GUI for DOS. That's the same bullshit I always read about Microsoft as Bill Gates alleged claim that "640KB of RAM are enough" for everything. Untrue, and unfair....

Define "legacy mode"....