The best and worst Windows versions ever

The best and worst Windows versions ever

Summary: By my count, Microsoft has released at least 10 distinct versions of Windows since 1990. Some evoke fond memories, some not so much. Which version was the best, and which was the worst? (Hint: They were released within a year of each other.) Read my ratings and then add your own.

TOPICS: Windows

In the Talkback section to my post on Vista’s slow start, commenter Arm A. Geddon does something I’ve been meaning to do for a while, which is to rate the various versions of Windows through the years and try to decide which ones were hits and which were misses. You can read his comments here for context.

I’ve been writing about Windows pretty much full-time since the very early 1990s, so I have vivid memories of every version, some fond, some not so much.

This sort of exercise is fraught with intellectual land mines. For one thing, any opinion is going to be influenced by one’s personal preferences, experience, and technical competence. More importantly, any such rating has to be placed in historical context. Windows NT 4.0 was excellent in its day, but I can’t imagine trying to use it today to get any work done. And finally, I’m going to factor in improvement over time, conceding that any initial release might have performance, stability, and compatibility issues but that the real test is how quickly and thoroughly those issues are dealt with.

OK, with that out of the way … All ratings are on a scale of 1 to 10, 10 being best.

Windows 3.x: 8+
It was miraculous in its day. After years of using DOS and a variety of clunky task-switching programs like DesqView I was thrilled to have a GUI and a real memory manager. From a tinkerer’s point of view it was pure gold (Brian Livingston’s original Windows 3.1 Secrets was roughly 1200 pages.) Windows for Workgroups 3.11 introduced TCP/IP support, and even included a network card (I think I still have the little Microsoft-logo’ed screwdriver that came with it). With Norton Desktop for Windows or PC Tools, you could have a shell that foreshadowed the full-blown GUI of Windows 95.

Windows NT 3.x: 3
It’s difficult to read the system requirements for the first NT versions today and then remember how expensive memory upgrades were. At PC Computing, we had NT on a system or two in the labs. Everyone thought it was cool and represented the future, but the lack of compatible software and hardware meant we couldn’t use it to get the job done day in and day out on the hardware we used.

Windows 95: 5
The potential was awesome. It was 32 bits! (Well, sort of.) DOS was dead! (Uh, kinda.) The reality was frustrating. Living through the evolution of Plug and Play was no fun, and the perennial problem of 64K system resource heaps meant that it had to be rebooted way more often than it should have. Two service releases got rid of some problems, and a steady stream of 32–bit applications made for fun. But if you ever had to install a network adapter or sound card you could kiss your weekend goodbye.

Windows NT 4.0: 8
Ah, a solid kernel and the Windows 95 shell. This one was my preferred computing environment on the desktop from the day it was released in August 1996, exactly one year after the Windows 95 launch.

Windows 98: 6+
This was what Windows 95 should have been, and the Second Edition was better still. NT was still a better choice for work, but I could use Windows 98 at home and install it on my Dad’s PC and be reasonably confident it would work. Most 16–bit programs had ridden off into the sunset by this time (although there were noteworthy exceptions like Quicken 98, which was still available in 16– and 32–bit versions).

Windows Me: 1
The worst Windows version ever, and doomed from the start. It was announced as the end of its line, it had to contend with Y2K fears, and it was buggier than a Fourth of July picnic on a Mississippi riverboat. The only feature that saved it from a zero is System Restore, which worked often enough to be useful if not dependable.

Windows 2000: 9
For its time, it was nearly perfect, and when businesses had to upgrade their hardware or be pitched into Y2K hell, it was the ideal choice. Tons of application support and good solid drivers. It’s no wonder some businesses still stick with it seven years later.

Windows XP: 6/8
Why two ratings? One for businesses, one for consumers. If you were running Windows 2000 already, you might have looked at the interface (“Fisher-Price” was the most common description) and said, “Huh?” But for consumers who were used to the crashes and mysterious lockups that were par for the course with the 16/32–bit hybrid 95/98/Me line, well … it was a giant leap forward in stability and reliability.

Windows XP Service Pack 2: 8+
As Jim Allchin told Mary Jo Foley, this could easily have been a separate Windows release instead of just a service pack. Microsoft really underestimated the security challenges that it would confront with Windows XP, and the improvements in SP2 really did make a difference. For businesses, it offers much better administrative tools and deployment options than Windows 2000. And after a few years the interface wasn’t so bad after all (and if you really hated it you could make it look just like Windows 2000).

Windows Vista: 5/8
I was tempted to punt and put in a question mark, because this sort of rating won’t really be valid until two or three more years pass. But in two years of beta-testing I think I’ve seen enough to make some preliminary judgments. The 5 is for businesses, the 8 is for enthusiasts. Vista is a solid platform with plenty of rough edges (UAC, anyone?) and its ecosystem needs another few months at least to catch up with it. At this point in its development its much like Windows 95 in its early days. Businesses are wise to take their time. Digital media enthusiasts have a lot to love. And if Microsoft is smart they’ll release a feature-rich update – not just a service pack - every fall.

OK, your turn.

Topic: Windows

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  • Ahhh, NT 4

    NT 4 rocked. I had several NT4 systems and they all ran for years with reliability that I've not experienced since. In fact, they all ran so well that I never had to reinstall any of them.

    Good days!
    Adrian Kingsley-Hughes
    • re: Ahhh, NT 4

      in total agreement. in fact, I still have an unused copy. :-)

      gnu/ choice to the neX(11)t generation.
      Arm A. Geddon
    • 1 thing about NT 4

      that lovely little service pack that hosed numerous machines, i believe it was SP3. It did do its job though.
      • re: 1 thing about NT4

        I believe it was Service Pack 4 that hosed more than a few systems. Also, don't forget the problems that SP6 caused, resulting in MS pulling it rather quickly, posting the 'fixed' version which wasen't, pulling it and pushing the correct SP6A. Caught a cold on that one, too!

        Other than those, NT4 on SP3 was sweet! Shame it needed SP4 or above for Y2K issues.
        • NT 4 SP5

          It was SP5 thst hosed my computer. I was doing the testing on it and had to reload the OS. Averaged about 4 hours to reinatll and update, in the days before imaging. Needless to say, we never deployed SP 5, and were justified in holding off on SP6 when SP6a was released a week later. Good times. I came into the business with NT 4 and got my MCSE. Still miss the clean look of the interface. Pretty candy land XP and Vista bring nothing to business enviroment.
          Kyser Soze
    • Remember NT4 GUI enhancments anyone?

      I think it was an Internet Explorer update I got with Quicken that added the quick launch tool bar to NT4. With quick launch added to the stability of NT4 it was my favorite OS till USB came along and I had to move to Win2000 to get good USB support. PC card support was also much better in Win2000.
      • See my post further down.

        “REAL Windows Versions.” As stated therein, installing Internet Explorer 4.0 on either Windows 95 or NT 4.0 added Active Desktop support, which included the Quick Launch bar and other enhancements to the 95/NT4 GUI that many think debuted with Win98.
        Joel R
        • Almost...

          It was the Desktop Update that came in IE 4, which included Active Desktop.

          I'm hyper-sensitive to the proper names on this one, since far too many people professed that Desktop Update = Active Desktop, which of course wasn't true.
    • I did

      At the one place I worked that used NT4, my system had to be re-imaged 3-4 times in the three years I worked there. At one point, I even lost Explorer - I could "Run" programs from the task manager (except for Explorer) but that was all - no interface.
      Beat a Dead Horse
    • NT4 stability

      NT4 was good but stability came with Win2K. It was through working with NT4 that I came to know the 'Blue Screen of Death'. These were all too often and unperdictable for my liking. I have only once had such an experience with Win2K. As for DOS, it is still one powerful little devil that I hope I never need to part company with.
      • BSoDs....

        ...are 90% hardware failure and 10% software bug....I've never seen one that can directly be attributed to the OS itself. To this day, MS is branded with the blame for "Blue Screens" when all they realy did wrong was provide too much information when the system crashed. Granted, the register dump and hardware interrupt is less than helpful in solving the problem, but it's really all you have to go on.
    • NT4: Beginning of the end

      The end of my weekends off: Working on multiple netware sites using Novell NDS and early clustering trype services, supporting thousands of users on only a few servers. Disks could be expanded without reboots, Services carefully loaded and unloaded with scripts to server acheved uptime in excess of 300 odd days on average on the critical file/print/mail servers.
      NT4 came along: Lets use these as file and mail servers say management.
      Install software - reboot. add new disk, reboot, change lan settings, reboot, patch one applicaiton, reboot. Virus attack, update AV and reboot. Oh, and we need twice as many servers as we need a domain controller in every office. Hey, how come I'm working more overtime than I used to?
    • Hardware support!

      Thats what I loved about NT4, it didn't care whether it was being moved between multiple computers with different HAL's.

      At ITT we got to the point that we used NT4 as our main OS and ran everything else in vmware, that is untile we became fluent in Linux.
    • NT 4.0

      Beautifully stable, but corporate use extended well beyond its support lifetime because of that. Fatal flaws included lack of USB support, as I recall.
      • "Falal flaws?"

        > Fatal flaws included lack of USB support, as I recall.

        The only thing "Fatal" about that flaw was that Microsoft exploited it to force you to upgrade. They could have added it, no problem but they preferred to grab your money instead even though forced upgrades cost you far more than just the price of the OS.
  • Rankings

    Ed, your rankings pretty much match mine, except that I like the Home version of Vista even more than you do. I would give it a 9. And I liked Windows Me less than you do. I would give it a big fat zero.
  • Perspective

    I think that your rankings are skewed by the fact that you're looking back so far.

    Win 3.1? Wasn't a huge improvement over earlier versions.
    Win 95? I'd give it a higher score. It was an enormous improvement for most users - along with the Pentium chip and AOL, it was the dawn of modern computing. Sure, it crashed and it didn't do everything it was supposed to do, but it was better than any successor until Win2K as far as consumer versions.
    NT4 and Win2K - great systems.
    XP (pre SP2) a huge improvement. More stable than ever.
    XP (post SP2) perhaps a bit of a resource hog, but still overall excellent.

    Xp is good enough that people don't feel the need to upgrade to Vista.

    Vista - haven't had enough experience with it to rate, yet.
    • Agreed mostly, except...

      "Win 3.1? Wasn't a huge improvement over earlier versions."

      It replaced Windows 2.1 (standard mode only) and Windows/286 and Windows/386. Those were terrible! Windows 3.0 was pretty good, Windows 3.1 much better, Windows for Workgroups was great.

      My rating of Windows 95 might be colored by my disappointment at its imperfections.
      Ed Bott
      • 95 Had one big plus

        It was pretty simple. I mis the days of a simple user interface. Yes I love how rock solid xp is although I tried real hard not too. I just think it could have done without all the bells and whistles. I could install 95 on a 500 mb disk. Yes mb not gb. There is still something to be said for a computer that sits there and does absolutely nothing until you tell it too.
        • "a computer that sits there and does absolutely nothing until "

          "you tell it too"

          Ah those were the days. When we were the masters of the machine and not the other way around.

          God, how I miss them!