Details of the new Microsoft (NASDAQ:MSFT) "Windows, not walls" ad campaign are trickling out, and it seems as if comedian Jerry Seinfeld will be the cornerstone of the marketing push.

On the surface, this is just a matter of Microsoft's getting over one Jerry -- Yahoo! (NASDAQ:YHOO) CEO Jerry Yang -- for another.

Dig deeper, and you'll find a Microsoft that is sick of being the butt of the "I'm a Mac, I'm a PC" ads, and is ready to fight back against Apple (NASDAQ:AAPL).

Having Seinfeld on board is a win for Microsoft because he had a Mac laptop in his sitcom apartment, back before Apple was cool.

This morning's Wall Street Journal is pegging the value of the campaign at a whopping $300 million, with Seinfeld receiving about $10 million of that for his appearance in ads alongside iconic Microsoft chairman Bill Gates.

Microsoft isn't above spending aggressively when it comes to marketing. Anyone else remember when the company shelled out roughly $12 million to use The Rolling Stones' "Start Me Up" to launch Windows 95?

The marketing likely will be more conventional than Microsoft's Mojave Experiment this summer, the daring campaign that took a group of XP users with strong anti-Vista views and tricked them into seeing Vista with fresh eyes. There's a rub with the guerrilla-marketing tactic. The moral of the Mojave story is that consumers are stupid if they don't upgrade to Vista. The new ads likely will position consumers as smart if they do.

Microsoft isn't the only company that needs this strategy to make Mr. Softy cool again. Computer makers like Dell (NASDAQ:DELL) and Hewlett-Packard (NYSE:HPQ), which have been smarting over Apple's market-share gains and anti-Vista sentiment, could use the boost.

Seinfeld may seem like an odd choice. He certainly is no young hipster. His hit sitcom has been off the prime-time airwaves for several years. His Bee Movie didn't do as much for DreamWorks Animation (NYSE:DWA) as the computer animation studio's more recent releases.

However, as someone who caught Seinfeld performing at a sold-out arena three weeks ago, I can assure you that hero worship is still alive and well across generations.

Microsoft considered younger comedians, including Chris Rock and Will Ferrell, before going with Seinfeld. It settled on a great multigenerational choice. I guess we'll see how it pays off once the ads start in two weeks.

But "Windows, not walls?" Sounds hokey.

Not that there's anything wrong with that.

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Longtime Fool contributor Rick Munarriz is a fan of Yahoo! and Microsoft, but not of bad weddings. He does not own shares in any of the stocks in this story, save for DreamWorks Animation. Rick is also part of the Rule Breakers newsletter research team, seeking out tomorrow's ultimate growth stocks a day early. The Fool has a disclosure policy.