Bill Gates' Legacy: Microsoft's Top 10 Flops

The Chairman isn't always right.

While Microsoft's outgoing Chief Software Architect Bill Gates has been ahead of the curve in predicting many technology trends, he also has backed some notorious flops.

Now that Gates officially has announced plans to relinquish his day-to-day company responsibilities by July 2008, we thought it would be a good time to look back on some of the less popular products and technologies championed by Gates during his 31-year Microsoft tenure.

Some of these, like Microsoft BOB, have gone to their graves. But not one to retreat from what might look like a losing battle, Gates has continued to beat the drum for more than a few of the items on our "flops" list.

In no particular order, here's are nine less-than-successful technologies Gates backed -- plus one he didn't that he should have but didn't – that will be part of his technology legacy.

1.Microsoft BOB (and son of BOB – Clippy): BOB, a product Microsoft released in 1995, was set to be the next-generation interface for Windows 3.1. BOB was Microsoft's first foray into making user interfaces more interactive and intuitive. (Clippy is the talking paperclip character that Microsoft users love to hate.) Interestingly, it was Bill Gates' wife, Melinda French Gates, who managed the BOB project.

2.Windows ME: Microsoft has rolled out a lot of versions of Windows since good old Windows 1.0 back in 1985. The most maligned of the bunch was Windows Millennium Edition, or Windows ME, which Microsoft introduced in 2000. ME was seen by many as a buggy upgrade with next-to-no compelling features. It was eclipsed rapidly by Windows XP, which Microsoft rolled out in 2001.

3.Tablet PC/Pen Computing/eBooks: While there is definitely a vociferous contingent of Tablet PC fans out there, the technology has been buggy and more expensive than expected. Many have been disappointed by the kinds of Tablet PC form factors -- including the new generation of Ultra-Mobile PCs (a k a "Origami") devices – that have made their way into the market. Microsoft recently decided to make Tablet PC functionality part of the base Windows Vista operating system, rather than to continue to champion it as a separate SKU.

4.SPOT watches: They're still big and dorky, even more than three years after the first Smart Personal Object Technology (SPOT) watch prototypes first hit the market. There still are no compelling apps or reasons to shell out hundreds of dollars for what are now known as "Smart watches."

5.Microsoft Money: If antitrust fears hadn't put the kibosh on Microsoft's plans to buy Intuit back in 1995, Microsoft might have been able to buy Quicken and turn its online banking product into a market leader. Instead, the Redmondians had to plod along with Microsoft Money, which seems to garner more wrath than praise from its users.

6.DOS 4.0: MS-DOS: No Microsoft look back can fail to mention the father of Windows, i.e., MS-DOS. Of all the QDOS (Quick and Dirty Operating System) derivatives, it seems to be the 4.0 release that Microsoft historians recall as the buggiest nightmare. Released in 1988, MS-DOS 4.0 was based on IBM's code base, not Microsoft, according to the virtual Wikipedia history books.

7.Microsoft TV: Microsoft has taken several stabs at making a go of the digital TV space, to no avail. Anyone else remember "Microsoft Tiger," the company's video-on-demand project launched back in the early 1990s? The company's not throwing in the towel on this one, by any means. In fact, Microsoft CEO Steve Ballmer recently said he believed IPTV would become one of the key Microsoft stock and profit drivers in the not-too-distant future.

8.MSNBC partnership/Microsoft as a content player: Microsoft's partnership with NBC was never a smooth one. In December 2005, Microsoft basically pulled back from its NBC relationship. But that isn't stopping Microsoft from continuing its long-standing quest to be a content provider in its own right. The company is in the midst of hiring bloggers, TV crew members and other media-savvy types to build something known as the "MSN Media Network."

9.Live Meeting web conferencing software: I'm still waiting to be bowled over by the need for presence and other "always on" technologies. Microsoft Watch readers know I am no fan of Live Meeting. But when asking others for input on this list, I wasn't the only one who thought Microsoft's Web conferencing product, based on technology it bought from PlaceWare, has been a disaster. Microsoft isn't folding its conferencing tent and going home, however; in fact, execs are promising the next versions of Live Meeting are going to be even bigger and more intrusive. Can't wait!

10.No Microsoft Linux!: Microsoft could have and should have done its own version of Linux. It could have bought a Linux distro vendor or just christened some branch of Windows (with some Unix-compatibility add-ons) as Microsoft Linux. By doing this, Microsoft could have thrown a real monkey wrench into Linux companies' plans. Instead, Microsoft continues to spend lots of money, time and attention fighting open-source software on a whole host of fronts. They should have joined the camp, rather than obsessing on beating them.