
20 years ago, Microsoft released a new version of Windows with a fresh new user interface that was built on the technical foundation laid by its predecessor. Sound familiar?
Look, I know that any Windows enthusiast who reads that headline is going to immediately judge it and then, in many cases, come up with some comparison they feel is more apt. That’s fine: That’s why we let people comment on the articles, here of course. But the more I think about it, the more this Windows 11/Windows XP comparison works.
To understand why it works so well, you have to remember how different things were in 2001. Microsoft had two Windows, one based on MS-DOS and one based on NT, and it had long planned to merge the two product lines, once it could figure out a way to use NT as the foundation of a system that also included the application and driver compatibility layers from the DOS-based Windows variants of the day.
Those efforts were to originally have culminated in Windows NT 5.0, which was quickly renamed by Microsoft marketing as Windows 2000 to drive home that fact. And while it is coincidental that I was so inspired by Microsoft plans for NT 5.0 that I started a little website called the Windows NT 5.0 SuperSite—later, the SuperSite for Windows—I also remember this time well.
And I have notes.

Windows NT 5.0—sorry, Windows 2000—would include the personalized menus from Office 2000, Internet Explorer 5.0, and “one-step sync” for mobile devices. It would be faster than the DOS-based Windows 98 on systems with 32 MB (yes, MB) or more RAM. It would equal Windows 98 in USB and general hardware compatibility (“it just works”), Plug ‘n’ Play (PnP), 1394 (Firewire), ACPI (power management), and DirectX 6 capabilities. And it exceeded 98 in its total cost of ownership (TCO), setup manager, sysprep capabilities, and so on. NT 5.0, we were told, would solve “DLL hell.”
NT 5.0 originally had a compelling consumer story, with its “auto-everything,” maintenance-free, and adaptive UI capabilities. Developer “richness” from the unification of the web and Win32 (which was reversed later), localization independence, and XML schemas (which would factor prominently in .NET and Longhorn later; in 1998, Microsoft did tell me it was “a key factor for the future”).
But Windows NT 5.0 would not provide a “UI shift,” and would instead bring forward the Windows 98 UI “with enhancements and simplification,” making it a “back to basics” release from a UI perspective.
Anyway, NT 5.0/2000 wasn’t the grand unification that Microsoft originally planned. And so, 18 months later, it released Windows XP—aka Windows NT 5.1—which shipped in both Home and Professional product versions, which could replace Windows 9x/Me and 2000, respectively. The foundation was there, from the NT-based side of the house, plus the driver and application compatibility models from 9x/Me. And, most crucially, there was a fresh yet familiar new user interface.

It was controversial. I described the XP user interface as “a sea of blues and greens,” angering a friend at Microsoft who had led the team that designed it. (We made up years later.) It, of course, came with three color themes—Bliss (blue and green), Olive (which was horrifically ugly), and Silver. But the plan was to provide theme packs over time that would further customize the UI to anyone’s liking.
That never happened, and for two reasons.
First, XP arrived just after Apple shipped the first version of Mac OS X, which featured advanced hardware-accelerated graphics with cool visual tricks like see-through UI elements and animations. And by comparison, XP’s bitmap-based UI, which had fixed-size elements, was both technically and visually inferior, a creature from a previous age.
Second and most problematic, Microsoft’s plan to extend the XP UI with a wide range of color schemes never came to fruition either, again because it was based on bitmaps and the firm had a hard time coming up with new color schemes that looked right everywhere. I liken this to the problem automakers have with paint colors: Because external car parts are all made of different mixes of materials, some paint colors don’t look the same on all parts and thus can’t be used. Microsoft ran into that wall quickly, and only two major UI additions ever appeared, a black theme based on Zune and the “Royale” theme that shipped with the second version of Windows XP Media Center Edition. So Microsoft plotted an OS X-like translucent UI, later called Aero Glass, for Windows XP’s planned successor, Longhorn.
But that’s history. The point here is that Windows 11 plays the same role today that Windows XP did 20 years ago. It’s based on the foundation of its predecessor, and it provides that fresh yet familiar new UI that really differentiates it. There are other improvements, too, of course, and that makes sense since the various product teams within the Windows organization are always pressing forward with new things, and some coming major upgrade is the ideal time to collect those together and get them in the product.
Windows 11 arguably won’t have the same longevity as Windows XP, but there are two interesting points there. First, XP was kept in the market and upgraded more over time than it would have been overwise, thanks to the Longhorn delays. (Projects like Windows XP Service Pack 2, SP3, and “XP Reloaded” all come to mind.) And we don’t know how Microsoft will upgrade Windows 11 over time yet. Will it be replaced by Windows 12 in two years? Or will we be dealing with new Windows 11s—with versions like 22H1 and 22H2—over a longer period of time?
We’ll find out soon enough. For now, it’s enough to know that Windows 11, as a refinement of what came before in Windows 10, is enough of an upgrade to warrant the name change and energize the fan base and, hopefully, the PC industry itself. It’s a great time to be a Windows fan, and I haven’t been able to make that claim in several years.
With technology shaping our everyday lives, how could we not dig deeper?
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