In this video, a Scottish computer nerd* named Andy installs MS-DOS 5, then Windows 1.0, and proceeds to upgrade through every major Windows version (except Windows ME, which we can all just pretend never existed), all the way to Windows 7. Now, I actually used Windows 1 and 2 — I ran them on an IBM XT clone, and felt that Windows 1 was pointless, though Windows 2 had a really cool clock app. It wasn’t until Windows 3 (and the famous “Windows 3.1 for Workgroups”) that the system became truly usable.

Andy writes about his experiment:

I got the idea from a 90s computer magazine article I vaguely remember (possibly from PC Format?), which essentially did the same procedure but only from Windows 3.0 to Windows 98. Since virtual machine technology is much more mature now, and there are four additional versions of windows, I thought it would be a great time to repeat the experiment. I installed Doom 2 and Monkey Island as tester applications, as I found the installation disks for them while I was looking for Windows disks, and those were two of my favourite games from the period (and still are).

The whole procedure took 3 days, of which approximately 12 hours was spent doing the actual installing – the rest of the time was spent trying to obtain valid copies of windows. One of the biggest problems was that Windows 95 and 98 came in two versions – Upgrade and Full. I had old disk copies of every Full version of Windows, but they cannot upgrade earlier versions. Luckily I was able to borrow a Windows 95 upgrade disk from a friend, and 98 was installed by renaming system files to trick it into upgrading.

I found this surprisingly entertaining. If you’re a computer nerd, perhaps you’ll enjoy seeing some Windows history, if only to remember the pain of watching Windows 98 install for hours and hours and [strangling noises]….

* = I use the phrase “computer nerd” lovingly, being one of them myself.