Please Vote for the Best and Worst Windows Versions of All Time

From 1.01 (1985) to 7 (2010?), a quarter-century's worth of Windows editions to love and/or hate. Help us pick the winners and losers!

By  |  Sunday, November 2, 2008 at 11:38 pm

Please vote for the best version of Windows in the first poll below, and the worst version in the second poll.

And lastly, if you have further thoughts on versions of Windows you’ve loved, respected, disliked, or loathed–and I hope you do–please leave them in the comments.

I thank you–and I can’t wait to see what the consensus is. Stay tuned for the results…




8 Comments For This Post

  1. Shemp DeYoung Says:

    My votes were the consensus votes so far.

    And I know of what I speak… I had ME on an eMachine. Yeesh. It turns my stomach just to think about it.

  2. Lawrence Velázquez Says:

    I voted Windows 3.1 as the best version solely because of my childhood memories of it. I had many hours of glorious Paint time.

  3. Dragos Stefan Says:

    There seems to be a mistake at pct. 9 (NT4) “[…] and long file names”. As far as I know, NT had long filenames from the start (NT 3.1)

  4. Dan Overes Says:

    I had to vote for 3.11 as the worst ever — anyone who ever had to configure WinSock and all those components to try and get that machine on a network knows what I mean.

    Windows ME is everyone’s favorite whipping boy, but I actually ran it for over a year with NO problems. Sure, it was bloated and full of crappy applications, but it still ran fine.

    XP SP2 gets my vote as the best of all time, but I could never go back to it after using Vista now for almost two years.

  5. NanoGeek Says:

    I voted for Vista. Before it came out, Microsoft made these huge promises about what it would include, but as the release date fell farther and farther behind, the great features kept being dropped. Now, there really are few features that I would want to have that I can’t have in XP with third-party software. Not to mention the fiasco that Microsoft caused with it’s “Vista Ready” labels before the release.

  6. Bill Greenberg - Good Computer Guy Says:

    XP SP2 is probably the best Windows – the most bang for the buck. I think Vista has to count for the worst because of a couple of reasons. First, the hype – ’nuff said. Second, it’s a resource hog – ridiculous how much hardware you need to run it. Sure, some of the earlier versions of Windows were painful (ugh, networking before W2K!) but I think they did pretty good given the state of technology. But for Vista to be where it is in 2008 is pathetic – they could have done so much better.

  7. Michael Thwaite Says:

    Vista is the best version of windows; certainly most feature rich but mostly because it was the first version to make good on the guidelines that were put in place many years ago; though shalt not write to the system folder, there will be no personal info in the app folder, you will break if you try.

    Vista has to go under the bus, be the sacrificial lamb, it’ll all be forgotten with Windows 7.

    MS says “We’ve learnt from our mistakes, Vista applications will work on Windows 7 forward compatibility is assured” notice that they don’t say XP applications will work on 7. No, Vista is a watershed release, it’s shaking out finally, all of the poorly written apps that break basic security rules paving the way for Windows 7 that everyone can like.

    Oh, and Windows XP Media Center wasn’t a release, well technically yes but really, it was a little silly; media center should have been a free download application.


  8. miguel Says:

    the speed of the 3.11 on my excel sheet was better than the speed on my windows 7 laptop