The best and worst Windows versions ever

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.

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.


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