Chain of Fools: a video experiment to upgrade every version of Windows

As a huge Reddit fan, I just had to share this awesome Windows-related video shared on the site that’s becoming popular.

The premise of “Chain of Fools”, although simple but extremely fascinating, is an experiment to upgrade from each major version of Windows to the next. That’s right, 26 years worth of legacy support from Windows 1.0 to Windows 7. The ultimate test of backwards compatibility if you will.

Subtly but not forgotten, Windows ME is missing. ಠ_ಠ

16 insightful thoughts

  1. You have to pick whether to upgrade Windows 98 to Windows 2000 or Windows ME. (Both 2000 and ME can both go on to XP, but there is no upgrade path between the two of them either way.)

  2. it would be interesting if they also ran the easy transfer tool for upgrades as well, it keeps more of the settings (like the background) around

    1. Most people wouldn’t think to run that tool. I never did. I went the hard route with everything.

  3. “Registered to: twatface”. I think I first saw it on the version check for Windows 98.

  4. The main reason Windows ME is missing could be because if i remember correctly. ME didn’t saved your settings at all and it was a highly error prone process. But i do remember upgrading several ME machines to XP though.

    1. The two versions of Windows I actually spent my own money on growing up, has been ME and Vista, so you can be sure I am so happy with Windows 7 which I have brought 3 copies of.

      Third time lucky eh!

  5. Now if someone can do or say the same for all linux distros or Mac OS X editions, I would like to see that. LOL

  6. That was pretty awesome to watch. Pretty ridiculous how we forget a lot of these details. I usually just format + install clean copies.

    Also. “twatface”. lol

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