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I love old technology as much as the next techno-geezer, but come on, it wasn't all wonder and goodness. After we're done reminiscing about the good old days of operating systems, let's reflect on the bad old days of operating systems as well. After all, the bad times are still with us — even in 2009, there are still some wretched operating systems out there.

In historical order, from oldest to newest, here's my own personal list of the top (bottom?) 10 OS stinkers.

OS/360, 1964

No, no, I'm not talking about the later versions of OS/360 that some of us used on IBM 360 mainframes back in the late '60s and early '70s. For its day, it was fine. Indeed, my very first operating system was an OS/360 descendant with TSO (Time Sharing Option) running on top of it.

What I'm talking about is the very first version of OS/360 — the one that led its project manager, Fred Brooks, to write The Mythical Man-Month, his classic book on how software development fails. That first version of OS/360, to paraphrase Brooks, came in late, had flaws in its control programs, required more memory than planned, was over budget by several times the original estimate, and, oh yeah, it was slow too.

On the other hand, we did get a classic book on how not to develop software, which included such nuggets as "Adding manpower to a late software project makes it later." Brooks likes to describe it as a software developer's Bible, because "everybody reads it, but nobody does anything about it." As the rest of this tale shall reveal, he was right.

ITS (Incompatible Timesharing System), late 1960s

What can one say about an operating system written in DEC PDP-6 and PDP-10 assembly language that supported one mono-case, six-character filename … per directory? (Yes, you read that right: Each file resided in its own separate directory.) And security was nil — for example, no passwords were required, and you could log into anyone's active session and do pretty much anything you wanted with it.

What's amazing is that despite being an incredible pain to use and with no security whatsoever, ITS actually was an important operating system in its day. While it was eventually forced out by the rise of Unix, many programs still in use today, such as the Emacs editor and the Lisp language, got their start on ITS.

For more on ITS and the early days of computer hackers, check out Steve Levy's classic book, Hackers. You'll find it entertaining and amusing, and you'll be very glad you didn't have to use ITS.

GNU Hurd, launched in 1983, still incomplete

Ever wonder why some people refer to Linux as GNU/Linux? The official explanation is that Linux is merely an OS kernel that relies on GNU software to make a complete operating system. GNU was announced in 1983 as a future replacement operating system for Unix, to be made up entirely of free software.

But after more than 25 years in development, GNU remains incomplete: Its kernel, Hurd, has never really made it out of the starting blocks. (I'll refer to the complete OS as "GNU Hurd" to avoid confusion with other GNU software.) Almost no one has actually been able to use the OS; it's really more a set of ideas than an operating system.

And that's why I'm naming GNU Hurd as one of my top 10 stinker operating systems — because after a quarter century, it has still failed to deliver on its promise of an entirely free Unix replacement. By incorporating ideas and software from GNU (and other sources such as Minix and BSD Unix), on the other hand, Linux has stepped in to pick up GNU Hurd's slack, providing an advanced operating system that is ready to use right now, in numerous distributions.

I, for one, am not willing to wait another 25 years for a chimera. Could we please just drop the dream of the GNU Hurd OS as an idea whose time will never come?

Windows 1.01, 1985

Microsoft's first attempt at a graphical user interface for MS-DOS was, in a word, dreadful. It was ugly, it shipped two years late and even then didn't work well. And besides, there wasn't anything that would run on it anyway. Windows applications really didn't get going until Windows 2.03 showed up two years later.

Adding insult to injury, by the time Windows 1 was launched, the Mac was already offering the far superior System 2.1. That Mac OS included AppleTalk networking, PostScript printing with the first LaserWriter printer and the first sophisticated PC-based file system: Hierarchical File System. There was no comparison.

MS-DOS 4.0, 1988

It's not like Microsoft was still spending much time in 1988 getting MS-DOS right. The earlier versions of the operating system really weren't bad for their day; MS-DOS 3.3 was actually quite good.

But then along came MS-DOS 4.0. Oh, it was horrid. Programs broke on it as regularly as clockwork. You'd be in the middle of a task, and your program would just freeze up completely. Nothing this bad was seen again until Windows' Blue Screen of Death.

To save their sanity, PC users either dropped back to MS-DOS 3.3 or moved to Digital Research's DR-DOS 3.41 as fast they could. Although the DR-DOS version numbers had been mimicking those of MS-DOS to show similar functionality, Digital Research chose to name its new 1989 version DR-DOS 5.0 to prevent anyone from thinking that it had any connection with MS-DOS 4.0.

SCO Open Desktop, 1989

On the plus side, it was the first 32-bit Unix with a graphical interface. On the minus side, its nickname was Open Deathtrap.

Open Desktop would, could, and did blow up in some of the most entertaining ways I'd ever seen. I had editors freeze up and compilers bring the entire system to a core dump — and there were times I never knew which, if any, window I was actually working in.

Strangely, I was actually able to get productive work done on Open Desktop. I suspect I might have been the only one who managed it.

JavaOS, 1996

Want to know a really bad idea for an operating system? Write it in a language that's as slow as mud — as Java was in 1996. Nevertheless, Sun, with some help from IBM, tried it anyway. JavaOS was designed to run on network computers and embedded systems.

How did it go? Well, let me put it to you this way: Have you ever heard of it? There are many well-known embedded systems: Qnx, VxWorks, Symbian, Windows CE and the list goes on. But even in embedded operating system circles, few people have ever heard of JavaOS.

Although several companies licensed it, the only product I know of that used it commercially was Sun's own long-forgotten JavaStation network computer. By 2006, Sun had dumped it into the "legacy system" junkyard, and that was the end of the Java-based operating system.

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 sjvn@vna1.com.

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