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Microsoft Bob
Introduced 1995, discontinued 1996
Poor Bob. No one ever gave him a chance. Maybe it had to do with the fact that he was really annoying. And as it turns out, Bill was dating Melinda French, Bob's program manager. Which isn't to say there was any nepotism involved -- Bob suffered an early death in 1996 due to general hatred for the little bastard. Bill offered this to a column in January, 1997, "Unfortunately, [Bob] demanded more performance than typical computer hardware could deliver at the time and there wasn't an adequately large market. Bob died." Thankfully, Billinda's blossoming relationship lived on. Oh, did you hear? They're like the world's greatest philanthropists now.


Cairo
Introduced 1991 (but never released)
Ask folks to pick one word to describe Microsoft's technology roadmap in the 1990s and you'll commonly get "Cairo" in response. Announced before Windows NT 3.1 was even released, Cairo was occasionally an operating system, occasionally a collection of new technologies -- it depended entirely upon who and when you asked -- but at its core, it was intended to guide Microsoft on the path beyond the architecture introduced by NT. After throwing countless dollars and man-hours at the ambitious project, Cairo was ultimately canned (though mentions of the storied buzzword continued even into this decade). Although Windows 2000 eventually became NT's heir apparent, the fruits of Microsoft's labor weren't entirely for naught, as various Cairo features found themselves implanted into various versions of Windows throughout the years. Even the WinFS file system can trace its roots back to the project -- fitting, because it too has become such an albatross.


MSN Music and URGE
Introduced 2004 and 2006, both fully discontinued 2008
When MSN Music -- Microsoft's effort to build its own PlaysForSure-based subscription music based store -- imploded, headstrong Bill did what he usually does: rebrand, and launch again. When he got up at CES 2006 and announced MSN Music would become URGE with MTV, we were all a little skeptical -- after all, the problem wasn't really the service, it was the overbearing DRM and the fact that consumers simply weren't ready for subscription music. Of course, eventually URGE died as well, and MTV shunted customers to Rhapsody America; naturally, Microsoft had a third PlaysForSure-based store waiting in the wings with Zune, which doesn't appear to be going anywhere any time soon.


Origami / UMPC
Introduced 2006
Note: Intel, please join Microsoft on stage to accept this award
UMPCs... what can we say? Sure, Scoble liked them, but even from day one we never saw the market potential. Fueled by an early and too-successful hype-generating viral campaign of Microsoft's own making, there was no way that these first generation Origami devices would achieve their promise. Overpriced, underpowered, desk OS-laden (with Microsoft's Touch Pack add-on), and poor battery life would ensure that UMPCs would need quite some time to live up to the wave of "ultramobile lifestyle PC"-hysteria they rode to market. And as UMPCs begin to fade, the shrinking niche between smartphones and laptops now looks toward to the sweet release of MIDs -- though that's already been two years... and counting.