Twenty years ago this month Microsoft released a stink bomb of an operating system, Windows Me. Unstable, unloved and unusable, that was Windows Me. Many people believe it was the worst version of Windows ever built.

The anniversary got me thinking: Was Windows Me really the worst Windows ever, or was it outdone by other notable flops?

I’ve used every version of Windows since the Windows 1.x version that shipped with the desktop publishing program Aldus PageMaker (later Adobe PageMaker), so I’ve had plenty of experience with the best and worst of Windows. Here’s my list of the worst three Windows versions of all time. I’m offering them in order of ascending horribleness, so you’ll have to wait to get to the bottom of the article to find the worst of the worst.

Drumroll please! Let’s get started.

Second runner up: Windows Me

Microsoft rushed out Windows Me (Millennium Edition) in September 2000, even though seven months before, in February, it had already released another millennium-named Windows, called Windows 2000. Why two Windows versions in one year? Because Windows 2000, which originally was going to be for both consumers and business users, ended up being only for businesses and was based on Windows NT. Microsoft wanted to make sure that consumers had a millennium operating system to call their own.

Microsoft shouldn’t have bothered. Windows Me was a ghastly, slapdash piece of work, incompatible with lots of hardware and software. It frequently failed during the installation process – which should have been the first sign for people that this was an operating system they shouldn’t try.

Often, when you tried to shut it down, it declined to do so, like a two-year-old throwing a temper tantrum over being forced to go to sleep. It was slow and insecure. Its web browser, Internet Explorer, frequently refused to load web pages.

Windows Me also introduced System Restore, designed to let you go back to a previous snapshot of Windows if you ran into trouble. Unfortunately, if you had a virus in that Restore Point that you had killed, Windows Me would restore the virus as well.

There are too many other issues to go into here, but the operating system was so bad  that people began calling it Windows Mistake Edition (Me), instead of the Windows Millennium Edition.

First Runner Up: Windows Vista

Ah, the special kind of badness that was Windows Vista. Released in 2006, five years after the well-received Windows XP, Vista was born under a bad sign, jinxed from the beginning, destined for failure. Work on it began five months before the release of Windows XP. It was supposed to be only a minor update to XP, to be released in 2003, a stopgap of sorts before a larger Windows update that was codenamed “Blackcomb.”

But developers will be developers, and soon many of the new technologies and features designed for Blackcomb nudged their way into Vista development, slowing things down drastically and leading to chaos and confusion during the development process.

Microsoft Co-President Jim Allchin, then in charge of Windows, admitted in a front page Wall Street Journal article on Sept. 23, 2005 that development of the not-yet-released Vista had been “crashing into the ground.” That would foreshadow exactly what happened when Vista was finally rolled out in 2006.

I don’t have enough space to recount the full extent of how bad Vista was, but start with the introduction of an intensely annoying feature called User Access Control (UAC), which forced people to confirm that yes, they really did want to change a particular setting or use a specific program.  It was a constant nag, requiring you to interrupt your work to do things as simple and basic as open Disk Defragmenter.

Vista was also notoriously unstable. It wouldn’t work with countless peripherals, including many popular brands of printers.

But all that pales in comparison with a far bigger hardware problem – the operating system simply refused to run, or ran so badly it was useless on countless PCs. Not just old PCs, but even newly bought PCs, right out of the box, with Vista installed.

There were several versions of Vista, and the consumer version of Vista was delayed until January 2007, after the 2006 holiday shopping season. Microsoft worried that people wouldn’t buy Windows XP PCs during the holiday season if they knew the PCs wouldn’t run Vista when that operating system was released in early 2007. So Microsoft cooked up a scheme to put “Windows Vista Capable PC” stickers on XP machines, in the hopes people would buy them during holiday shopping.

There was only one problem with that bait-and-switch scheme. Many “Windows Vista Capable PCs” weren’t in fact capable of running Vista, something that even Microsoft executives admitted to each other in private.

A class action suit was launched against Microsoft as a result. Emails from top Microsoft executives uncovered during the suit were remarkably damning. Mike Nash, then a corporate vice president for Windows product management, wrote in an email, “I PERSONALLY got burnt…Are we seeing this from a lot of customers?…I now have a $2,100 e-mail machine.”

Jim Allchin, a member of the company’s Senior Leadership Team, wrote in an email, “We really botched this…You guys have to do a better job with our customers.” And an unnamed Microsoft employee chimed in via email, “Even a piece of junk will qualify” to be called Windows Vista Capable.

All in all, Windows Vista was about as bad as it gets. Although not quite as bad as it gets, thanks to our winner.

The baddest of the bad: Windows 8

You want bad? You want stupid? You want an operating system that not only was roundly reviled by consumers and businesses alike, but also set Microsoft’s business plans back years?

Then Windows 8 was the Windows for you. If you instead wanted a useful, solid operating system that made your life at the PC easier, you had to wait for Windows 10.

So much was wrong with the worst operating system Microsoft created that it’s hard to know where to begin. Let’s start with the most basic. It wasn’t really a single operating system, but rather two separate OSes badly bolted together.

One was built for mobile touchscreen devices, and wouldn’t run applications built for the desktop, Win32 apps such as Office. That part of the operating system was designed from the ground up to work via touch, not by keyboard. It also was designed to run apps that Microsoft through the years has called Metro apps, Universal Windows Platform apps, Windows Store apps, and now, just Windows apps.

The other operating system inside Vista was the one that had been around for years, with a desktop and Win32 apps and everything that went along with it. That’s the operating system that nearly everyone used, because when Windows 8 was released, there were few Windows tablets. But in Windows 8 everyone was forced to live with the problems and limitations of an operating system designed for touchscreen tablets.

People were forced to wrestle with a useless Start screen designed for mobile rather than the desktop. And they were forced to constantly switch back and forth between a traditional desktop and that Start screen.

As for those Metro apps, they were significantly underpowered, to the point of being useless. They couldn’t be resized, so they took up the entire screen, unlike Win32 apps. And there were hardly any available. At the time, I wrote that the Windows Store, from where you download them, was “as barren of goods as a Romanian grocery store during the depths of the Ceauşescu regime.

Many of Windows 8’s problems were due to Microsoft’s decision to use it as a blunt force object to become a mobile powerhouse. At the time, Windows Phone was an abject failure and Microsoft felt it had to make a splash in tablets. So it decided to build an operating system built more for mobile than the desktop. And it decided to create Metro apps which would theoretically someday also work on Windows Phone.

That all-in approach to mobile on Windows 8 led to Microsoft’s buying Nokia’s mobile business for $7.2 billion – and Microsoft eventually shutting down that business. Microsoft spent years trying to succeed in mobile, depriving the rest of the company of resources, money and time.

It wasn’t until Satya Nadella was hired as CEO and changed the company’s focus towards the cloud and away from mobile and Windows that the company began to recuperate from the disaster of Windows 8.

Will we ever see another Windows as bad as Windows 8? Not likely. With Windows 10, Microsoft no longer makes drastic changes to Windows. What you see today is what you’ll see tomorrow and a long time into the future, with only modest changes along the way.

So Windows 8 will likely hold the crown of the worst Windows ever, for as long as there’s a Microsoft.

Copyright © 2020 IDG Communications, Inc.



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