1996-present: Every name ever associated with handheld devices running Microsoft software. At first, they were called Handheld PCs, and ran an OS known as Windows CE. Then they morphed into Palm PCs--until the PalmPilot people complained, whereupon they became Palm-Size PCs. But only briefly: Soon, Microsoft wanted us to call them Pocket PCs, and the software they ran was renamed Windows Mobile.
That name stuck around when the OS migrated from PDAs to phones, although it bifurcated into two editions: Windows Mobile Pocket PC and Windows Mobile Smartphone. Then Microsoft declared that there were three Windows Mobile variants--Windows Mobile Classic, Windows Mobile Professional, and Windows Mobile Standard. As for the devices themselves, Steve Ballmer declared in February of this year that they'd be known henceforth as Windows Phones--scratch the "Mobile." Except for the fact that the OS is still Windows Mobile. Got that?
What they should have been called: Melvin. Or just about anything else, really, as long as it didn't keep changing.
2000: .NET. In the mid-1990s, critics accused Microsoft was accused by many of being slow to jump on the Internet bandwagon. By the dawn of the new millennium, however, it was firmly on board--and in June 2000, it unveiled a vision for online services it called .NET. As originally articulated, .NET addressed consumers, businesses, and developers, and it involved everything from programming languages to an online version of Microsoft Office to calendaring and communications services to a small-business portal to stuff for PDAs, cell phones, and gaming consoles. It was so wildly ambitious, so all-encompassing, and so buzzword-laden that it pretty much defied comprehension, at least if you weren't a professional geek. Which the company seemed to realize--it quickly stopped pushing the concept to consumers, instead restricting it to programming tools.
What it should have been called: How about "Virtually Everything Microsoft Does Involving the Internet From This Day Forward," or VEMDIFTDF for short? Or taking a different tack, what if Microsoft had simply declared that it was now Web-centric, period--no new branding required?
2000: Windows Millennium Edition. Microsoft couldn't call this successor to Windows 98 "Windows 2000" because it had already assigned that name to Windows NT's replacement. So the company saddled the OS with a name that was both pretentious and goofy, and gave it the overly adorable (and badly capitalized) nickname "Windows Me." It was probably bad juju: The product itself went on to be widely reviled as slow, glitchy, and insubstantial; and to this day its name rivals that of Microsoft Bob as shorthand for "crummy software."
What it should have been called: Windows 2001, especially if Microsoft marketing had assembled an ad campaign involving HAL 9000 and/or apes hurling things at an obelisk. Bonus virtue: That name would have given Microsoft an excuse to delay the OS for six months to fix bugs.
2001: HailStorm. Hail isn't exactly a form of weather resplendent with positive associations: It kills crops, damages cars, blinds drivers, and is downright painful--and occasionally deadly--to people unfortunate enough to get pelted by it. Yet that's the codename that Microsoft chose to associate with the plans it unveiled in 2001 to deliver an array of Web services and to store consumers' personal information for use with Microsoft and third-party offerings.
The notion of Microsoft controlling so much private data proved instantly controversial; the company changed HailStorm's name to .NET My Services, and then put the whole idea on hold And yet HailStorm wasn't so different from services that Microsoft, Google, Facebook, and others offer today. I can't help wondering whether it would have fared better if it hadn't had a name that suggested a violent weather disturbance descending from the heavens to afflict us mere mortals.
What it should have been called: Microsoft Passport--a name Microsoft gave its online ID service even before it announced HailStorm--wouldn't have been bad. Today, however, Microsoft Passports are known as Windows Live IDs (presumably to distinguish them from all those Windows IDs that have died).