VOTW: Every Major Windows Upgrade On Video

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Windows has been around a long time, and even if you are old to enough to have been around since day one, upgrading every time a new version comes out, it’s doubtful many of you have installed version after version on the same machine.

So what would happen if you installed every major upgrade version of Windows, in order, on the same computer? A 26-year-old UK YouTuber going by the name of TheRasteri decided to give it a shot and find out. He skipped ME because you can't go from ME to 2000, only from ME to XP. According to him it was a choice between 2000 and ME so, "[he] went for 2000 as it was chronologically the next release." And, because, you know, ME is ME.

Check out the video below to see for yourself.

Jane McEntegart
32 Comments Comment from the forums
  • thomaseron
    I've been thinking about installing Windows 95 on my SSD, just for the fun of it. :-) The whole operating system is like 150-200 MB in size when installed, and my SSD averages on about 150MB per second in readspeed...
    Reply
  • dragonsqrrl
    OMG this is freaking awesome... epic sweet experiment. Too bad about the color settings not carrying over after XP, they just don't make em like they used to, lol. I'm amazed at just how many legacy programs survived the trip all the way to Windows 7, very impressive.
    Reply
  • Randomacts
    rofl good stuff
    Reply
  • Zracko
    Awesome Work, Brings back some happy and not so happy memories
    Reply
  • sudeshc
    Really good experiment enjoyed watching it.
    Reply
  • fuzzyplankton
    He's 28? I am 30 and i was just a kid using windows 3.1. So he he must of teething on the keyboard for windows 1.0
    Reply
  • jeverson
    Not bad but they left a few Win OSs out. Win ME, Win NT 3.51, and Win NT 4.0. I find it strange since they bothered to go from Win 98 to Win 98 SE. But I must say it was kinda fun to see those old OSs again. Although I'm not sure why the installs took so long. I don't think it has ever taken me longer than 35-45 min to install any version of Win. Then again I have always made it a practice to format and install fresh vs upgrading because I have always run into issues with using the upgrade option.
    Reply
  • endgadget
    Really wish that pages like Engadget would stop being negative towards windows as they even had a negative comment for this article. Respect to Toms for staying impartial.

    Either way, loved the video and it obviously brought back memories.

    Here's another great video that seems to have escaped
    http://www.youtube.com/watch?v=VHkPiU9YAQk
    Reply
  • alidan
    jeversonNot bad but they left a few Win OSs out. Win ME, Win NT 3.51, and Win NT 4.0. I find it strange since they bothered to go from Win 98 to Win 98 SE. But I must say it was kinda fun to see those old OSs again. Although I'm not sure why the installs took so long. I don't think it has ever taken me longer than 35-45 min to install any version of Win. Then again I have always made it a practice to format and install fresh vs upgrading because I have always run into issues with using the upgrade option.

    the difference between 98 and 98se is so vast they could have made a new os out of it. at least if i remember right.
    Reply
  • iamtheking123
    Nice memory lane trip. Still have a laptop running 3.1 that has to be launched from DOS. The infamous 98 install screen. That black bar / blue window on the installer still haunts my dreams, especially since 98 had a tendency to self destruct itself and need to be reinstalled every few months.

    I agree with skipping ME and NT since those never were popular. My own usage path was 3.1->95->98 SE->2000 (dual booted with 98 so I used 98 most of the time)-> XP SP2 -> XP SP3 -> Vista -> XP SP3 -> XP SP3 / Win 7 dualboot but SP3 still most of the time.
    Reply