The 10 Worst Microsoft Product Names of All Time

If Microsoft had invented the iPod, it would have been called the Microsoft I-pod Pro 2005 Human Ear Professional Edition. The cult-hit video that makes that assertion may have been a joke, but it rings true. And when word emerged that the video was a self-parody produced within Microsoft, the point was even clearer: The world’s largest software developer just isn’t very good at naming stuff.

Some Microsoft names sound clunky; some are confusing; some are undignified or overambitious. More than any other company in technology, the Redmond powerhouse loves to change product names–often replacing one lackluster label with an equally uninspired one. Microsoft has also been known to mess up some names that are actually perfectly good, such as Windows and Word, by needlessly tampering with them.

Herewith, in chronological order, are ten Microsoft names that could have been a lot better, together with some semiconstructive advice on monikers that would have more euphonious and/or more accurate. I also selected six not-quite-as-bad runners-up.

1993: Word 6.0 for Windows: When Microsoft upgraded 1991’s popular Word 2.0 for Windows, it replaced it with…no, not something logical like Word 3.0. Rather, it blithely hopscotched over three version numbers and landed at Word 6.0. The official explanation for the skippage was that it brought the Windows edition’s version number into line with that of the older DOS incarnation of Word. But conspiracy theorists noted that it also allowed Word to catch up with archrival WordPerfect, which also released a version 6.0 in 1993.

Whatever the rationale, the move rendered the practical purpose of version numbers meaningless, thereby setting a bad example for other companies such as Netscape, which later went straight from Netscape Navigator 4.0 to version 6.0.

What it should have been called: Word 3.0 for Windows. Simple and accurate.

1995: Microsoft Bob. When I asked my Twitter and Facebook pals to nominate bad Microsoft names, this legendarily lousy Windows front-end hosted by animated characters came up far more often than any other product. It’s possible that the badness of the product has tarnished its title. But as several people pointed out, “Microsoft Bob” is both cutesy-cute and uninformative–it doesn’t give you an inkling as to what the product is all about. (The box featured a smiley face wearing Bill Gates-like nerdy glasses, but the main character in the interface was a dog named Rover, who was later revived for Windows XP’s misbegotten search feature.)

What it should have been called: Well, Microsoft Rover would have been at least slightly more descriptive–especially since the product itself was such a dog.

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).

2004: Windows Genuine Advantage. Understandably, Microsoft hates it when people pirate Windows. So it added multiple copy-protection measures such as activation and validation to Windows XP and Windows Vista. Collectively, they’re known as Windows Genuine Advantage, which the company touts as a benefit to properly licensed users. But WGA asks paying Microsoft customers to jump through piracy-detecting hoops. Worse, it’s been known to accuse them of stealing Windows and shut off functionality.

What it should have been called: Snarky answer: Windows Genuine Disadvantage. Serious one: Windows Anti-Piracy Technology.

2004: PlaysForSure. This logo program for services and devices that used Windows Media DRM may have been the single most inaccurately named item in the history of personal technology. The name exuded hubris, but PlaysForSure tracks often FailedToPlay on PlaysForSure-enabled devices–and, of course, they didn’t play at all on the world’s most popular MP3 player, arch-rival Apple’s iPod. For Pete’s sake, they didn’t even play on Microsoft’s own music player when it appeared. By the time Microsoft shut down the PlaysForSure-powered MSN Music service, it had already rolled PlaysForSure into the blandly named Certified for Windows Vista program, which doesn’t promise much of anything. What it should have been called: MusicCripplingWindowsMediaDRM. Or just plain Windows Media, which is what PlaysForSure was beneath the patina of marketing hype.

2006: 2007 Microsoft Office System. When Microsoft announced Microsoft Office 2007 in February 2006, it started calling the overall Office platform the “2007 Microsoft Office System,” even though individual versions, such as the alarmingly wordy Microsoft Office Professional Plus 2007, kept the year at the end of the name. At the time, a Microsoft representative explained the distinction to me, but I barely comprehended it even then–it was as if the company wanted Windows 95 to be called 95 Windows in certain instances. Then there was the superfluous “system” on the end, which reminds me of how the Disney company insists on calling Disneyland the “Disneyland Resort.”

What it should have been called: Microsoft Office 2007. Actually, that’s what everybody outside the city limits of Redmond does call it.

2008: Windows Live Essentials: In September 2008, Microsoft announced that it was stripping three of Windows Vista’s applets–Windows Mail, Windows Photo Gallery, and Windows Movie Maker–out of Windows 7. They would live on, but as free downloads, known collectively (along with other apps such as Windows Live Writer) as Windows Live Essentials. But doesn’t the fact that Microsoft unbundled these tools from Windows prove that they’re not essential? Bonus annoyance: Microsoft’s decision to identify these downloadable freebies’ under the Windows Live rubric (which usually applies to Web services) makes it even harder to define just what Windows Live means.

What it should have been called: I’m not sure that anyone gains anything by giving these applets a collective name. But something along the lines of Windows Bonus Material or Windows Extras would work.

Next: Six runners-up.

Runners Up: Six More Unfortunate Microsoft Names

Chkdsk. Even in the DOS era, it was unclear why the name of this venerable disk-checking utility skipped all its vowels; even with the eight-character filename limit it could have at least been Checkdsk or Chekdisk. Today, there’s no excuse for not calling it CheckDisk.

All Microsoft products called Messenger. Not that it’s inherently bad name. But there’s Windows XP’s Windows Messenger; there’s the unrelated command-line utility called Windows Messenger Service, famous mostly for being a security leak; and there’s the old MSN Messenger, which was renamed Windows Live Messenger in 2005. That’s at least two Messengers too many. To its credit, though, Microsoft didn’t change “Messenger” to “Message Explorer.”

Microsoft Office Word. And Microsoft Office Excel, Microsoft Office PowerPoint, and Microsoft Office Access. With Office 2007, Microsoft stuck in a superfluous “Office” in the middle of some of the best-known names in the history of software. Nobody noticed. Basic rule of thumb: If your customers don’t realize that you’ve changed your product’s name, you’ve failed.

OneNote. Merriam-Webster reports that “one-note” means “monotonous.” Microsoft’s handy note-taking application deserves better.

The Road Ahead. Published in 1995, Bill Gates’s best-selling book famously didn’t predict the rise of the Internet, thereby utterly failing to live up to the visionary promise of its title.

Windows 95: Yes, seriously: By the time it finally shipped, 1995 was two-thirds of the way over, leaving the blockbuster new version of Windows sounding slightly stale from the get-go. And it ushered in the era of consistently inconsistent Windows names, from additional year-based ones (Windows 98, 2000), to inappropriately highfalutin’ modifiers (Windows Millennium Edition, Windows Vista) to mysterious acronyms (Windows XP).

Are there other tech-product names you find annoying and/or inaccurate–from Microsoft or from other companies? Or maybe even names you think are really good? Sound off in the comments.