If you never had the chance to see Mojo Nixon perform before he retired, then you missed a spectacle. Some claim Mojo was unsavory. Others derided him as the psychobilly messiah. More than a few left his shows laughing in disgust. But he was cool. And one thing he knew was that you can’t buy cool.

Which is exactly what Microsoft is attempting to do, which is pretty uncool.

I’ll wait to see what disaster the unholy union of Steve Balmer, Jerry Seinfeld and $300,000,000 creates. The stated intent of Microsoft’s next advertising campaign is to blunt the market mind-share created by Apple’s highly viral Mac vs. PC advertising and provide Vista with more any positive brand image.

$300,000,000 may not be enough.

A central tenet of branding is authenticity. When a company creates a brand it must have some close resemblance to reality or at very least not utterly violate the markets perception. Customers can detect pure hype and will create a maelstrom of negative buzz when they do.

Let’s be blunt – Windows may be dominant, but it ain’t cool, hip or groovy. Vista, doubly so. Any attempt to out cool Apple is doomed to failure.

Press reports indicate that Microsoft will instead attempt to extend their “Windows, Not Walls” branding. Cutesy slogans aside, they will attempt to convince buyers that Vista opens users to more uses and activities.

Which goes against what is happening in the market.

Desktop operating systems are becoming increasing irrelevant to consumers who now use their computers (Macs, PCs, Linux-netbooks, cell phones, etc.) primarily to access the net. Operating systems are the support layer and not the source of usefulness and consumer joy. Making Vista cool when more and more of consumer time is spent with YouTube and JibJab misses customer focus and thus creates a false brand.

In an earlier memo I suggested that instead of investing in Vista, Microsoft should have focused on integrating the net as part of the desktop experience — intimately wedding desktop functionality to cloud content. I know of nothing in Vista that expands that horizon. If such features are hidden in Vista, then having Seinfeld out them would be a good first step – though they could have had me do a better job for a good deal less than Seinfeld’s $10M fee.

Years ago Silicon Strategies Marketing codified the definition of branding:

Branding is making the market think and feel what you want them to think and feel about your products

But there are limits to what you can make people think or feel. Try making a mother hate her baby or force people to believe that pizza tastes bad. Making people feel that Windows is cool or think that Vista isn’t a resource hog is pushing far beyond the market’s experience and mindset. Microsoft needs baby steps in resurrecting Vista’s image. They need to lead the trend for using the net. They need to make the operating system a relevant partner to the electronically integrated world.

That would be cool.