The 10 Worst Operating Systems of All Time

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Windows Me (Millennium Edition), 2000

Until another Microsoft operating system came along a few years ago, Windows Me was the bottom of the Windows barrel. This successor to Windows 98 SE, ranked No. 4 on PC World's list of the 25 worst tech products of all time, tried to be both a 16- and a 32-bit operating system. It worked about as well as a horse with wheels for front legs and hooves for back legs.

It was also slow, unstable and insecure. OK, so those are all traits of Windows in general, but Me took it to an extreme. How bad was it? Microsoft sold it for only a little more than a year. Now, that's bad.

Lindows/ Linux XP Desktop, 2001/2006

What happens when you try to put Linux and Windows together? Nothing very good. Lindows, when it first came out in 2001, promised to let you run all Windows applications on Linux. Lindows Inc. gave up on that as a bad idea within a few months. Even with WINE, a way to run Windows programs on Linux, the company couldn't get enough Windows programs running on Lindows to sell it as a Windows replacement.

Showing that some dumb ideas won't die, Russia-based TrustVerse has also tried the "We'll be everything Windows, but we're Linux" approach with Linux XP Desktop. It doesn't do much better with this idea than Lindows did; it does a mediocre job of running Windows applications, and its XP look and feel isn't anything to write home about. If you really want to run Windows applications on Linux, get CodeWeavers' CrossOver Linux.

Windows Vista, 2006

You knew this one was coming. Do I really need to recount everything that's wrong with Vista -- its bloat, its slowness, its hardware and software incompatibilities, its high cost, its confusing versions, its security fumbles and other ineptitudes?

Or how about the fact that several of its vital features wouldn't work on computers bearing a "Vista Capable" sticker? Let me share with you one early "review" of Vista:

"I chose my laptop (a Sony TX770P) because it had the Vista logo and was pretty disappointed that it not only wouldn't run [Aero], but more important wouldn't run [Windows] Movie Maker. ... Now I have a $2,100 e-mail machine."

This review's author? Mike Nash, Microsoft's corporate vice president of Windows product management, in an internal e-mail dated Feb. 25, 2007. Go argue with him, Microsoft fanboys, not me.

Need more proof that Vista's a dog? Let's see ... a third of new PCs are being downgraded to XP, and Microsoft keeps extending the cutoff date for XP sales while hurrying Windows 7 to market as quickly as it can. Woof woof.

So, there you have it, my list of stinkers. What do you think? What are your favorite operating system losers? Do you still use Open Desktop? How about Vista? Let me know in the article comments.

[ Can't get enough of bygone operating systems? See "Gone but not forgotten: 10 operating systems the world left behind."]

Steven J. Vaughan-Nichols has been writing about technology and the business of technology since CP/M-80 was cutting-edge and 300bit/sec. was a fast Internet connection -- and we liked it! He can be reached at

This story, "The 10 Worst Operating Systems of All Time" was originally published by Computerworld.

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