I promise we’ll stop commemorating the 15th anniversary of Microsoft Bob after today–and today is the anniversary of the app’s formal release–but bear with me for one last item. Bob’s great significance isn’t as a piece of software–it’s as an albatross around Microsoft’s corporate neck. Just about everyone who wants to take a swipe at a new Microsoft product finds it expedient to compare the item in question to Bob. And in that respect, it’s eerily similar to another product released five years later: Apple’s G4 Cube. Like Bob, the Cube was launched with immense fanfare but sold poorly and died after a year. And it, too, is an albatross–one that will live forever as the product people bring up when they want to predict that a new Apple offering is going to be a dud.

After the jump, a quick comparison of these unexpected soulmates, in the form of a T-Grid.

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Thinking back to my youth, my dad suffered from deal myopia. He was always looking for one, and couldn’t pass up buying whatever appeared to be the best value for our family. Sometimes those deals turned into ordeals– like the time when he purchased a PC that was preloaded with Packard Bell’s Microsoft Bob-like front end. I thought about it as I read our coverage of Microsoft Bob‘s fifteenth anniversary today.

The Packard Bell that was rigged to boot into an interface called Packard Bell Navigator, an alternative shell for Windows that was designed to make using a PC easier. It presented the user with a virtual study instead of the Windows desktop and had a brief and unremarkable existence during the mid-1990s. But it predated Bob, and surely reached far more people–Packard Bells may have been famously shoddy, but they were also the era’s best-selling home PCs.

Our prior family PC had run Windows 3.x, and we had a great collection of shareware games. I became proficient at booting into games from DOS, and prior to that, a Commodore 128. The Packard Bell and its virtual room interface befuddled me. It was difficult to determine which objects had any function or not. My greatest discovery was learning how to turn it off.

In all fairness to my dad, he did make some good buys from time to time. The Commodore was incredibly fun, and prior to that, my siblings and I played on a Magnavox Odyssey. (There weren’t any deals on Ataris.)

The Odyssey still sits in my mother’s basement, and I may attempt to get it running again at some point in the future. Thanks dad–let’s just forget about that Packard Bell…Sears riding mower, fiberglass pool lining, and the Didi Seven.

I didn’t include this in my history of Microsoft Bob, but maybe I should have–and it’s too fascinating not to share.

In 2008, in Microsoft’s own TechNet magazine, Windows team member Raymond Chen reported that the Windows XP CD included some dummy data as part of an anti-piracy scheme, and that the person who implemented it had some fun with the project:

…he dug through the archives and found a copy of Microsoft Bob. He took all the floppy disk images and combined them into one big file. The contents of the Microsoft Bob floppy disk images are not particularly random, so he decided to scramble up the data by encrypting it. When it came time to enter the encryption key, he just smashed his hand haphazardly across the keyboard and out came an encrypted copy of Microsoft Bob. That’s what went into the unused space as ballast data on the Windows XP CD.

Even if it’s true, it’s a delightfully urban legend-y tale. And no, it didn’t appear in the April issue of the magazine–but it’s almost the same story as one that was an April Fool’s prank.

We’re talking about Bob here, so anything’s possible. Bob being snuck onto Windows XP CDs is no stranger a concept than Bob existing in the first place…

What’s the most efficient way to deride a technology product as a stinker and/or a flop? Easy: Compare it to Microsoft Bob. Bring up the infamous Windows 3.1 front-end for computing newbies–officially released fifteen years ago this week, on March 31st, 1995–and you need say no more. Everything from OS X to Twitter to Google Wave to (inevitably) Windows Vista has gotten the treatment.

Bob’s pervasiveness as an insult long ago transcended its brief period of prominence as a product. By now, it’s unlikely that the vast majority of people who use it as shorthand for “embarrassing tech failure” ever actually used it–any more than the average person who cracks jokes about the Ford Edsel has spent time behind the wheel of one.

But Bob didn’t start out as one of technology’s most reliable laugh lines. It may strain credulity given Bob’s current reputation, but back in 1995, even pundits who had their doubts about the software seemed to accept the idea that it was a sneak preview of where user interfaces were going. And even though Bob died just one year later, Microsoft continued to Bob-ize major applications for years–most notably every version of Office from Office 97 through Office 2003, all of which featured the notorious Office Assistant helper, better known as Clippy.

In its own odd way, Bob is ripe for rediscovery. Hence our fifteenth-anniversary celebration, which includes the story you’re reading; a guided tour of Bob in slideshow form; and memories of Bob and its offspring from Tandy Trower, who worked at Microsoft for 28 years. Whether you’re appalled by Bob, defiantly enchanted by Bob, or never knew Bob at all, read on–and let us know what you think.

(Thanks to Dan Rose, Rogers Cadenhead, and David Worthington for their help with our Bobfest.)

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Think that Microsoft Office’s Clippy was a joke? Microsoft didn’t–Google Patents holds proof of the serious effort that the company poured into ever-unpopular animated “helpers” like Clippy, Microsoft Bob, and the Search Assistant. The whole idea remains baffling, but the drawings that Microsoft filed are weirdly fascinating. I’ve assembled a gallery of highlights.

View Secret Origins of Clippy slideshow