Microsoft's $300 million makeover

Remember that $300 million consumer ad campaign that Microsoft awarded earlier this year?

New specifics are emerging on how the ad agency that won the deal -- Crispin Porter + Bogusky -- is starting its task of rebranding Microsoft as a cool company. Crispin Porter counts Burger King, Molson, Volkswagon and Virgin Atlantic among its high-flying clients.

The Crispin folks say they like a challenge. They have one on their hands with the Softies. From the Fast Company article on the ad agency:

"Microsoft's already problematic reputation in some circles -- as the soulless, power-hungry purveyor of lackluster products -- has suffered a series of self-inflicted wounds. It spent two years and $500 million on the media blitz around the long-delayed Windows Vista launch, only to see the January 2007 'Wow' campaign, which likened Microsoft's new operating system to Woodstock and the fall of the Berlin Wall, derided as arrogant and creatively void."

Can Microsoft ever be seen as hip as Apple? Seems like a tall order. The article continues:

Countering that (Microsoft) nebbishy, pocket-protected image now falls to Crispin. And Bogusky's team is revved up at the prospect. 'There was a time,' says Jeff Hicks, Crispin's CEO, 'when it was Avis against Hertz, Coke against Pepsi, Visa against American Express. I think Microsoft is at the epicenter of the great brand challenge of the next decade -- or millennium.'"

If you were helping Crispin spend that $300 million, what would you do to try to help Microsoft out of its Vista marketing morass? One blogger thinks Microsoft would be well-served to use Chairman Bill Gates, in spite of his imminent retirement from day-to-day duties at Microsoft, as the centerpiece of its campaign. Thoughts?