"If a book about failures doesn't sell, is it a success?" Perhaps not, but Microsoft hopes that a new $300 million ad campaign about the flailing Windows Vista will somehow turn it into a success with the help of comedian Jerry Seinfeld. The campaign will be one of the largest in Microsoft's history, and is expected to begin on September 4.

In fact, Seinfeld may not be the only celebrity involved in the new Windows Vista campaign. The ever-popular "people close to the situation" have informed the Wall Street Journal that Seinfeld is simply "one of the key celebrity pitchmen" that will appear alongside Bill Gates to discuss Vista's merits. According to the WSJ's sources, the company has also considered Will Ferrell and Chris Rock among a multitude of other personalities, although there was no indication as to whether they had also been hired as part of the campaign.

The new ads will be spearheaded by a new agency for Microsoft and one famed for a number of Burger King ads, Crispin Porter + Bogusky (boy, would I hate to be at that agency right now—talk about pressure!), and are expected to center around the slogan "Windows, Not Walls." Clearly, the idea here is to emphasize that Vista can help users connect with others and complete their tasks instead of providing obstacles. And of course, employing well-loved celebrities that are known for their widespread appeal can't hurt either... Microsoft hopes, anyway.

The move comes almost two years after the operating system was first launched to the public. Since then, there has been an unending stream reports about users and businesses downgrading from Vista back to Windows XP, spurred by any number of issues from sluggishness to numerous driver issues. Manufacturers like Dell and Lenovo have even offered to downgrade customers to XP for free thanks to user demand.

Vista's reputation has certainly taken a beating since its launch, and Microsoft said last month that it was finally going to do something about it. Microsoft's VP of Windows Vista consumer marketing Brad Brooks mentioned Apple by name as being a "noisy competitor" after having taken a number of pot-shots at Vista in its own Get a Mac campaign, and vowed to strike back with its own ad campaign. "You thought the sleeping giant was still sleeping? Well, we've woken up, and it's time to take our message forward," Brooks said during the company's Worldwide Partner Conference.

The new ad campaign will be part of Microsoft's general "Vista really is better than you think!" push that began earlier this year. Microsoft first started advertising the "real Vista story," and then soon followed up with the now somewhat-infamous Mojave Experiment, the Pepsi Challenge of the Windows world, where users learned that Vista isn't so bad after all. The question remains, whether the new advertising push will end up being too little, too late. Had a similar campaign been launched soon after Vista's release (and of course, if Vista's launch was a little more smooth for some users), perhaps the company wouldn't be scrambling right now to fight back against the little guy in order to resurrect sales.

In the meantime, Apple will continue to pummel Vista with its own somewhat-annoying, but apparently effective "Get a Mac" campaign. Will Seinfeld be able to out-funny John Hodgman and Justin Long? We await the results of this new front on the platform war with bated breath.