Remember Windows XP? What about Windows 98? …95? How far back does your relationship with Microsoft’s Windows operating systems go?

While I cut my technical teeth on Windows 2.1 I recall, with more than a little fondness, using Windows version 3.1 through-out high school. I remember all of the geek buzz the summer after graduating (class of 95) about the amazing new version of Windows that was soon to be released. One of the hottest topics? It was rumored to come on a either 13 floppy disks or, for the first time ever, a CD-ROM! That was a big deal back then if you can believe it.

Operating systems have come a long way over the years improving to keep in synch with leaps in hardware technology. While the earliest versions of windows look incredibly simple and rather oafish, keep in mind that today’s operating systems are ‘standing on the shoulders of giants’ – owing all of their power, technology and features to versions that came before.

These days most people purchase package computers complete with pre-installed operating systems, so you may have never experienced the geek-fueled anticipation of an upgrade. The sheer excitement as the upgrade progress bar crept up pixel by pixel, inexplicably sticking sometimes at 34%… then again at 52%… and again at 64%. Minute after agonizing minute, sitting… staring at the progress bar – willing it to lurch orward and indcate the installation was complete.

Windows version install experiment

The experiment? Install the first version of Windows (or rather it’s predecessor) DOS, then upgrade each version to the next newest version to see what happens. A few of the criteria that the experiment is tracking is installation time, personalized settings (color, fonts etc), and viability of installed software from instance to instance – to see what information is maintained and retained from version to version.

For me this was an incredibly nostalgic walk down a geeky memory lane – for some this may be an education in early geekdom, and for others still this might seem to be a pointless exercise in madness. Check it out and decide for yourself

For more information check out the original post on upgrading through every version of Microsoft’s OS Windows.