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VOTW: Every Major Windows Upgrade On Video

By - Source: TIME | B 32 comments

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.

Chain of Fools : Upgrading through every version of windows (HQ)

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  • 3 Hide
    thomaseron , March 4, 2011 4:20 AM
    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...
  • 1 Hide
    dragonsqrrl , March 4, 2011 4:23 AM
    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.
  • 1 Hide
    Randomacts , March 4, 2011 4:23 AM
    rofl good stuff
  • Display all 32 comments.
  • 0 Hide
    Zracko , March 4, 2011 4:32 AM
    Awesome Work, Brings back some happy and not so happy memories
  • 0 Hide
    sudeshc , March 4, 2011 6:00 AM
    Really good experiment enjoyed watching it.
  • 0 Hide
    fuzzyplankton , March 4, 2011 7:14 AM
    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
  • -2 Hide
    jeverson , March 4, 2011 8:25 AM
    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.
  • 0 Hide
    endgadget , March 4, 2011 8:28 AM
    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
  • 0 Hide
    alidan , March 4, 2011 8:56 AM
    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.
  • 0 Hide
    iamtheking123 , March 4, 2011 9:09 AM
    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.
  • 0 Hide
    thomaseron , March 4, 2011 9:22 AM
    iamtheking123Nice memory lane trip. 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.


    My usage path was 3.0->3.11->95a->95b->98->98SE->ME->98SE->2000+SP->XP->XPSP1->2->3->Vista->XPSP3->W7x64. :-)Millenium was thrown out after the first time I attempted a reboot. The one right after the installation, you know? BSoD! And back to 98SE it was! :-D
  • 0 Hide
    killerclick , March 4, 2011 11:23 AM
    Why didn't he say how long it takes to install Windows 7? As I remember it's very quick, under 30 minutes or so. What a jerk!
  • 0 Hide
    caeden , March 4, 2011 12:21 PM
    usage for me was:
    Doss with Moo Menu, win3.11, 98, 2000/98SE dual boot (my first computer), XPsp1, XPsp2, XP64bit, briefly back down to XPsp3, back up to XP64bit when some hardware drivers were fixed, Win7 RC1, Win7 Home 64bit, and am now itching for win8RC but I guess it is going to take a while.
    I remember after a few years of 98 having to go back and fix a win3.11 computer and being so frustrated at the lack of context menus, or much of anything else for that matter, but I don't remember being frustrated by it when it was all I knew. Same with win7 vs XP. I went for about 2 years on win7RC/Home and now have to use XP at work and it is really frustrating.
    Win2K and win7 are my favorites so far.
  • 0 Hide
    tserich , March 4, 2011 1:30 PM
    Ah Good Ol' Monkey Island! I loved that game :) 
  • 0 Hide
    jplarson , March 4, 2011 1:31 PM
    I went from Win95, Win98, Win98 SE (my first pc, Compaq Presario 7470), WinXP Home, WinXP Pro SP1-3, WinXP Pro 64-bit SP2, Win Vista Ultimate 64-bit SP2, Win 7 Pro 64-bit RTM-SP1.

    Never got into DOS so much and I had friends with Win 3.11 but the first computers I played around with had the familiar GUIs. Vista worked great for me SP2 on rocking hardware, so I don't have the bitter hatred others do for it. Then again I didn't upgrade to it until my old 32-bit XP Pro machine died well into Vista's lifecycle and I got it on student discount.

    I remember how great XP was for networking when it first came out. The reboots from 98SE drove me nuts when I had to change things up.
  • 0 Hide
    z06psi , March 4, 2011 2:46 PM
    That was awesome...good job
  • 0 Hide
    tomus , March 4, 2011 2:54 PM
    Started puting when you had to plug the patch cords in on the back of the machine to do your programming.

    Linux rules.
    It's like the logo "have it your way."
  • 0 Hide
    rpgplayer , March 4, 2011 3:17 PM
    @ 4:04 - 4:06 LOL, I guess I'm not the only one that puts in BS terms in username and company fields
  • 0 Hide
    clonazepam , March 4, 2011 3:18 PM
    Ah the memories... As a demonstration to a class I taught about a particular shipping software program, I put 2 computers side by side. One installed Win95 and the other installed the shipping software... hehe the race was on. Of course Win95 won every time so the recruits learned don't stay on the phone waiting for an install... get another call ;) 
  • 0 Hide
    starryman , March 4, 2011 3:53 PM
    Pretty cool... BUT I wish they would have done this on a physical machine from the 90's rather than VMware. The biggest problem for all of the Windows upgrade paths has been the physical hardware requirements. There's no way this straight upgrade path could have been done on a machine back in the early 90's. So maybe on a another try, try a new machine (not on on VMware) and start from MS DOS an up. I'd like to see the benchmarks, hard disk space usage and bootup times.
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