Is That The Conquistador? They Run Tight.

Microsoft has kicked off its $300 million ad campaign to extoll the virtues of Windows Vista...with Jerry Seinfeld and Bill Gates meeting at Shoe Circus.

Well, you’ve got to give Microsoft one point: they didn’t produce a conventional television ad.

Software giant Microsoft has kicked off its $300 million ad campaign to promote its Windows Vista operating system with a spot featuring comedian Jerry Seinfeld and Microsoft founder Bill Gates having a chance meeting at a fictional store called Shoe Circus, Seinfeld helping Gates into a pair of size 10 “Conquistadors,” and Bill Gates “adjusting his shorts” as a signal Microsoft has big things in the works. The ad is available via Microsoft’s Web site using the company’s Silverlight technology; copies are also popping up on YouTube.

The ad is notably content-free, mentioning almost nothing about Microsoft itself or WIndows Vista. But it does offer a few humorous insider jokes, such as an early Bill Gates mugshot being used on his “Platinum” Shoe Circus membership card, and having the courage to make the commercial’s clincher a shot of Bill Gates giving a little wiggle of his butt.

Will it be enough to derail John Hodgman and Justin Long in Apple’s successful “I’m a PC…and I’m a Mac” advertisements? Time will tell.

According to Microsoft, the new ad campaign is about how consumers can use Windows technologies on the PC, on mobile devices, and on the Web to improve their everyday lives. The message is that Vista is not yesterday’s Windows.

“When you think of more than a billion people using Windows across the globe, each person with a unique set of circumstances, and then factor in three Windows platforms and what they can do, it’s hard to even comprehend the number of unique scenarios Windows can potentially address,” said Microsoft’s corporate VP for Windows Consumer Product Marketing Brad Brooks, in a statement. “We wanted to know how customers experience not only the products, but the company itself. We did our own studies, engaged with leading research firms and really evaluated not only how our products work for the average person, but how our business works for them.”

We’re not sure how having Jerry Seinfeld explain to a shoe salesman that Bill Gates is a “ten” figures into that…but maybe it triggers into a backdoor in Windows Media Player so it connects back to Microsoft and downloads a video explaining the whole thing? Maybe Shoe Circus is a metaphor for Apple? (And Bill Gates has a platinum card? That can’t be right….) Whatever the connection, Microsoft has decided to abandon the straight-on “Windows is great!” approach of previous campaigns, and—for the next few minutes anyway—people are talking about it.