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

11. Windows 98 Second Edition (May 1999)

The Good: As an update to Windows 98, which was itself an update to Windows 95, Windows 98 was a refinement of a refinement, and probably the most solid Windows 9.x that Microsoft ever shipped. It came with Internet Explorer 5.0 and introduced Internet Connection Sharing, and benefitted from all the fixes that Microsoft had made to Windows 98 in the 14 months since its original release.
The Bad: It was still Windows 9.x, which meant it was an aging product built on rickety technology that dated back to the introduction of the IBM PC in 1983.

12. Windows 2000 (February 2000)

The Good: This successor to Windows NT 4.0 was still aimed at businesses rather than consumers, but rolled multiple useful features from Windows 98 (like Internet Explorer 5, Outlook Express, and Windows Media Player) into the OS. It was therefore both more reliable than any version of Windows 3.x and instantly familiar. There was a time when plenty of sophisticated Windows users preferred it to Windows XP.
The Bad: Microsoft touted W2K as the most secure version of Windows ever…which didn’t stop hackers from compromising it early and often.

13. Windows Millennium (September 2000)

The Good: The last version of Windows 9.x introduced some minor interface updates and functionality tweaks, and System Restore, a theoretically useful data-recovery utility that cloned the then-popular GoBack.
The Bad: PC World named Windows Me as the fourth worst product of all time. Despite Microsoft’s “It Just Works” mantra, Me was notorious for just not working. And for being unbearably sluggish. And for the fact that System Restore sometimes reinstalled viruses you’d just gotten rid of. It was a sad swan song indeed for Windows 9.x

14. Windows XP (October 2001)

The Good: At long last Microsoft brought the 32-bit goodness of the Windows NT platform to a version of Windows aimed at both consumers and business users. (Okay, XP wasn’t one version of Windows–it came in a Home version and a Professional one–but you get the idea.) It was far more reliable than the misbegotten Windows Me, or any other 9.x variant of Windows.
The Bad:
Thanks in part to XP’s longevity–it remains the dominant version of Windows seven years after its release–it’s probably caused more people to spend more time wrestling with security issues than any other operating system ever. And its user interface was a glossier refresh of Windows 95’s look more than a major leap forward.

15. Windows XP Media Center Edition (January 2002)

The Good: It was the first version of Windows tuned for the living room, with an interface you could navigate via remote control from the comfort of your sofa, TiVo-like TV recording, and more.
The Bad: True story: I once attended a demo of a Media Center PC from one of the largest computer companies in the world during which the PC froze. Several executives responsible for the thing crowded around it and couldn’t shake it back to life. Eventually, they figured out that Norton Anti-Virus was displaying a warning about lapsed signature updates that was being covered up by the Media Center interface. Which neatly summarizes the downside of bringing a device that gets viruses into your living room.

16. Windows XP Tablet Edition (November 2002)

The Good: Microsoft, high on the notion that laptops would evolve into pen-driven tablets, released a stylus-driven version of Windows that let you tap your way around the interface, save “ink” notes, and do basic handwriting recognition. The people who loved this approach to computing really loved it, and I continue to meet them to this day.
The Bad: There turned out not to be all that many of those people. Perhaps in part because Tablet Edition didn’t do the one thing you really want from a pen-driven operating system: perform accurate, easy handwriting recognition. Microsoft ended up rolling its features into Windows Vista, but seems to have lost interest in the whole idea.

17. Windows XP SP2 (August 2004)

The Good: This may have been a mere service pack, but it was a better Windows upgrade than some theoretically bigger ones, with scads of security-related fixes, the Windows Firewall, a pop-up blocker, and various improvements to multimedia and wireless support. In fact, Windows Vista’s iffy reception clearly stemmed in part from SP2’s success in making millions of people feel happy and productive.
The Bad: SP2 may have incorporated scads of security fixes, but they hardly resulted in a Windows that was a mighty fortress.

18. Windows Vista (January 2007)

The Good: The first major new version of Windows in more than five years added the flashy Aero interface, new security measures such as User Account Control, desktop search, Windows Gadgets, and more.
The Bad: Rarely had a new version of Windows fallen so short of living up to Microsoft’s hype: Much of Vista simply caught up with stuff that was already available as free downloads. And early adopters were bedeviled by compatibility and performance woes.

19. Windows Vista SP1 (February 2008)

The Good: Many, many fixes for issues with the initial version of Windows Vista, plus support for some newer technologies such as 802.11n networking.
The Bad: A more robust Windows Vista is still pretty ho-hum, and SP1 introduced no new features. Also, PC World’s performance tests didn’t show SP1 to be an advance over plain old Windows Vista. Did I mention that the first version of SP1 caused PCs to spontaneously reboot, forcing Microsoft to pull it from the market?

20. Windows 7 (???)

The Good: It looks like the next version of Windows–available in a reasonably promising pre-beta version now but not due for final release until late next year or early 2010–will be a much less annoying version of Windows Vista.
The Bad: It looks like we’ll have to wait until late next year or 2010 for the next version of Windows, and that it’ll be nothing more than a less annoying version of Windows vista.

Whew. That’s a lot of Windows, and lots of pros and cons.

Got a Best Version of Windows and a Worst Version of Windows in mind? Click to go to the next page, and cast your votes…




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