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You know Microsoft is hopelessly out of touch when the opening paragraph of the Wall Street Journal article that's supposed to be touting the tech giant's marketing coup starts off something like this: "Microsoft Corp., weary of being cast as a stodgy oldster by Apple Inc.'s advertising, is turning for help to Jerry Seinfeld." Huh? Microsoft is hoping to appeal to the Gen Y demo—people in their 20s—by hiring a spokesman who is 54? Better yet: Seinfeld will be appearing in the commercials alongside Bill Gates himself, who doesn't exactly conjure up an image of cool with iPod-listening, Macbook-carrying hipsters on the L train. The $300 million campaign, which will debut on Sept. 4th, will be promoting Microsoft's Vista operating system, which, company officials acknowledge, has generated a "negative public perception." (That's probably because it sucks.) Why did Seinfeld decide to participate? We're guessing it may have had something to do with the $10 million paycheck.

Microsoft came up with the near-retiree on purpose: "People familiar with the Microsoft campaign say that the company was aware of trying too hard to pander to youth, so didn't want a celebrity that was too hip, or a possible flash-in-the-pan."

This makes sense, of course. Hiring the Jonas Brothers wouldn't have been the wisest move. But then again, hiring someone who hasn't had a hit in a decade doesn't quite add up either. And considering the agency involved is Crispin Porter + Bogusky, which famously came up with those viral Burger King commercials, you have to wonder if Microsoft could have come up with something more inventive. But there's a silver lining! Seinfeld won't be playing the role of Superman this time around. And Jessica Seinfeld will have her Barneys bill covered for the next year or two.

Microsoft Enlists Jerry Seinfeld In Its Ad Battle Against Apple [WSJ]