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

It’s the most popular product in the history of personal technology. It’s also the one that’s inspired the most angst–not to mention a landmark court case or two. But Windows isn’t one product. Over its twenty-three year history, it’s been available in dozens of variations. Some got glowing reviews; others still cause those who remember them to wince at the mere thought of them.

But which version of Windows was the most impressive one ever–and which one was the most awe-inspiring fiasco? I have my theories. But I thought it would be more fun to let you make the call.

Hence this article. I’ll recap some of the essentials on twenty editions of Windows, from the prehistoric (version 1.01) to the futuristic (version 7, available today only in a pre-beta incarnation); you can click on the title of each listing for more information over at Wikipedia. Once you’ve read up, please vote on the best and worst, and use Comments to praise or rant at greater length if you choose. We’ll use this feedback as the basis of an article we’ll publish in the not-too-distant future.

This survey involves only desktop versions of the OS that ran on x86 CPUs–sorry, Windows NT for DEC Alpha and Windows CE buffs–and I haven’t included each and every version, just the major ones and some others with a reputation for being particularly outstanding or excruciating. You can also cast write-in votes if you’re an aficionado or enemy of Windows/286 or Windows XP SP1 or another version we skipped.

The rundown that follows includes pros and cons for each edition, but I won’t pretend it’s entirely dispassionate–it’s hard to write about Windows without expressing opinions. Don’t be swayed by my slant on things, though. Just vote honestly (hey, it’s anonymous). The list starts after the jump, but if you don’t need to brush up before voting, you can head straight for the poll. Oh, and please tell your friends about all this–the more opinions the merrier…

1. Windows 1.01 (November 1985)

The Good: It provided a basic graphical front-end for the otherwise text-only world of MS-DOS–and you could drive it with that newfangled input device called a mouse.
The Bad: It bore about as much relation to the Mac as a Yugo does to a Mercedes: It was ugly as sin, and you couldn’t even overlap windows. And in a precedent-setting move, Microsoft started hyping it two years before it arrived.

2. Windows 2.0 (November 1987)

The Good: You could overlap windows, and Word and Excel debuted in Windows versions, giving folks the first apps worth buying Windows to run.
The Bad: It was still pretty homely compared to the Mac and other graphical environments such as that of the Amiga. (Even so, it prompted Apple to sue Microsoft, in a long-running lawsuit that probably didn’t do anyone involved, including Mac and Windows users, any good.)

3. Windows/386 (May 1988)

The Good: This version of Windows was designed to take advantage of the power of Intel’s potent 386 CPU–it could multitask DOS applications and featured better memory management than previous versions.
The Bad: It may have been a significant leap from a technical standpoint, but Windows still looked dowdy. And DOS was still beloved: The majority of PC users didn’t understand why you’d want to mess it up with needless complications like a graphical interface.

4. Windows 3.0 (May 1990)

The Good: It was the first version of Windows that was…kind of slick, actually. Compared to DOS, anyhow. And for the first time, companies other than Microsoft started to write lots of Windows applications with real graphical interface. Consequently, it became the first version that was a hit. Oh, and it included Solitaire for the first time.
The Bad: The resemblance to the Mac was there, but it was barely even skin-deep: DOS’s eight-character file name limitation lived on, and you still had to wrangle with DOS’s memory limitations. Oh, and major software vendors such as Lotus still thought that IBM’S OS/2 would replace DOS, and therefore focused their energies on it.

5. Windows 3.1 (March 1992)

The Good: Microsoft took the wildly popular Windows 3.0, added lots of fixes that made it more reliable–and introduced added TrueType, giving Windows built-in scalable font technology for the first time.
The Bad: Windows not only had never caught up with the Mac OS, it was falling behind: Apple’s System 7, released the year before, had file sharing, the first version of QuickTime, and lots of other features that left Windows looking like a relic of the 1980s.

6. Windows for Workgroups 3.11 (November 1993)

The Good: The trendy concept of “workgroup computing” got its own edition of Windows, with built-in networking capabilities. But it was also the most highly-evolved, stable version of Windows 3.x, period–so much so that plenty of folks stuck with it even once Windows 95 arrived.
The Bad: Mac partisans were still entitled to mock the lack of long file names; devotees of IBM’s OS/2, which was still alive and kicking, also got to look down upon Windows users.

7. Windows NT 3.5 (September 1994)

The Good: For the first and last time to date, Microsoft rewrote Windows from the ground up to make it more robust and modern–and for the first time, it turned it into a true 32-bit operating system rather than a front-end for for the 16-bit antique known as DOS. (Version 3.51, released in May 1995, added some minor fixes and features and was available in a version for Power PC-based computers.)
The Bad: This OS was stuck with the Windows 3.x user interface even after Windows 95 rendered it obsolete. And it wasn’t compatible with Windows 3.x drivers.

8. Windows 95 (August 1995)

The Good: Long file names! The Start Button! The Taskbar! And no need for DOS! Windows 95 fixed most of Windows’ most glaring problems, and introduced most of the interface concepts that define the OS to this day. People were so eager to get their hands on it that they really did line up at CompUSA at midnight. And for once, a Microsoft ad campaign–complete with Rolling Stones soundtrack–was widely regarded as hip.
The Bad: Windows 95 may have been a full-blown OS in theory, but DOS, and some of its drawbacks, lurked under the surface–architecturally, this was no Windows NT. And Microsoft managed to ship an OS that arrived simultaneously with the birth of the consumer Internet without including a Web browser or the ability to connect to the Internet. (You had to buy the Windows 95 Plus Pack to get ’em.)

9. Windows NT 4.0 (July 1996)

The Good: It took almost a year, but Windows NT finally got a Windows 95-style interface, with the Start Menu and Taskbar, and long file names.
The Bad: NT still lacked some of Windows 95’s key conveniences, including USB (added to Win 95 via an update) and Plug and Play peripheral setup.

10. Windows 98 (March 1998)

The Good: Windows 98 wasn’t radically different from Windows 95, but it was the first version of the OS to include USB from the get-go and it introduced Windows Driver Model (WDM) drivers, which are still in use. It booted up and shut down faster, and supported multiple monitors for the first time.
The Bad: The OS also introduced the questionable Web-desktop integration known as Active Desktop and the dead-on-arrival, justly forgotten WebTV for Windows.

1 2 3 NEXT PAGE»



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