Cityfile: New York's Most Notable and Influential

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.More