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OS/2
Dates: introduced 1987, discontinued 2006
What began as a collaboration between Microsoft and then-partner IBM blossomed into what looked like -- for a time at least -- the logical successor to the DOS / Windows empire. The advanced OS showed early signs of greatness with it's incorporation of the HPFS file system, improved networking capabilities, and a sophisticated UI. But cracks in the relationship between the two powerhouse corporations would ultimately lead to its downfall. With Windows 3 a sudden success, IBM's reluctance to go hardware neutral, and Microsoft's increasing displeasure with code which it called "bloated" (ahem!), the project was eventually swept aside by Gates and the gang to make way for what would become the omnipresent operating system you know and love and/or hate today.


SPOT watches and MSN Direct
Introduced 2004, discontinued 2008
When the concept of an information-enabled watch that automagically received content over unused FM radio subcarriers was first conjured up by Microsoft in the early part of the decade, it seemed like a fabulous idea. So much so, in fact, Bill personally took the project under his wing. But by the time it had launched, it was already doomed by a perfect storm of problems: the devices were uglier than sin and comically oversized, the bizarre ad campaign featured frighteningly hairy cartoon arms, and -- as the mobile web was just starting to pick up steam at that time -- virtually anyone who would've been interested in that kind of product had already discovered ways to get the same information from their phone. The underlying data network Microsoft built out to support the watches, MSN Direct, lives on to this day and sees plenty of use in Garmin's nüvi line, but will it ever be used to beam weather, news, and MSFT stock reports to wrists other than Bill's? Not bloody likely.



Windows Activation
Introduced 2001
Depending on who you talk to, Windows Product Activation is a serious privacy violation, a headache, minimal protection against piracy, or all of the above. Lucky for us, Microsoft is finally seeing (some of) the folly of its overbearing ways, and has gone with a more permissive nagware method with Vista SP1. This as opposed to the regular method of routinely locking users out of their systems, which, wouldn't you know it, tended to hurt legitimate users more than pirates. Perhaps the best example of Windows Activation's legacy was the great WGA outage of 2007, which left 12,000 systems out in the cold due to a few downed servers at Microsoft. It didn't take long for the servers to bounce back, but any shred of reputation the service had at that point went out the window with the uptime.


Windows ME
Introduced September 2000
It's not exactly clear what the point of Windows Millennium Edition was -- our guess is that Microsoft needed to keep up with that year-based product naming scheme it had going at the time, and cranked out this half-baked update to '98 in order to capitalize on the turn-of-the-millenium frenzy. Unlike the NT-based Windows 2000 released at the same time, Windows ME retained its MS-DOS-based core, while managing to somehow get even more slow and unstable than its predecessors 95 and 98. And to add insult to injury, it restricted access to shell mode, rendering many MS-DOS apps incompatible. Thankfully, Windows ME was only inflicted upon consumers for little over a year; it was replaced by indomitable Windows XP in 2001.


Windows Vista
Introduced 2007
Vista doesn't suck. Let's just get that off our chests. In fact, it's a quite capable, secure and sexy OS when you get right down to it. Unfortunately, its problems just loomed too large for many folks to overlook. A multitude of delays and a rapidly diminishing feature list soured people right out of the gate, and once the dust settled people just weren't happy with the minor improvements they were getting in exchange for their hard-earned monies and fairly mandatory RAM upgrades. Mix that in with the standard driver incompatibilities of any Microsoft OS upgrade, and you've got a whole bunch of disgruntled downgraders on your hands -- and plenty of bad press to fill in any remaining gaps. Sadly, improvements to Media Center, aesthetics and even that quirky little sidebar got overlooked in the process. Microsoft's already scrambling to get Windows 7 together to capture the multitude of users that've decided to skip Vista altogether, let's just hope it's not too late.

Runners-up: Actimates, Pocket IE, Games for Windows - Live, Xenix (yeah, Microsoft actually did a Unix at one time!)