Well, no, you probably can’t because I challenge anyone to run a modern OS in graphic mode with a 20 years old hardware. Nevertheless, if that was possible, would it be possible to have a MS-DOS 5 OS and upgrade it to Windows 7, going through (almost) every OS Microsoft made in the last 20 years ? Apparently you can. Some of the original programs will even have carried over from Windows 1.0 all the way to Windows 7.
That’s probably the best ad ever for Microsoft, if you ask me.
Now of course this doesn’t account for the fact that you need to reinstall Windows (any version) anywhere between every 3 to 12 month, but let’s not be pedantic.