TO SAY THAT MICROSOFT has an image problem is like saying halitosis would make a bad jelly bean flavor. A fact made painfully clear 24-7 in endless Apple “I’m a Mac” commercials, Microsoft epitomizes über-nerddom—the bitter, pudgy, rumple-suited cube-dweller in thick glasses and a bad haircut. Enough! snorts the Redmond software company, which has ponied up $300 million to score cool cred. First it threw a bunch of that dough at ads featuring comedian Jerry Seinfeld playing his lovably sarcastic “Jerry” character opposite Bill Gates’s supposedly lovable mope. The two go on adventures (they buy shoes, they live with a family in the Seattle burbs) and exchange Seinfeldian banter, the idea being, “Look, everyone loves Jerry, and Bill hangs with Jerry, so…” Next came an ad that geek-slapped “I’m a Mac” with testimonials from cool people—actress Eva Longoria, hip-hop icon Pharrell Williams—swearing that they’re avid PC users.
Will any of it work? Not a Twinkie’s chance in Newman’s apartment, says Seattle branding consultant Rob Osler. “What works with the Apple ads is that they reflect the Apple brand convincingly and clearly,” chides Osler, whose clients include T-Mobile, Alaska Airlines, and, yes, at one point, Microsoft. “I’m not sure if the Microsoft campaign really is a true, authentic reflection of the core Microsoft attributes,” he says. It’s “big, powerful, technologically competent, but not a cutting edge innovator…. The Zune is a response to the iPod. Xbox is a response to PlayStation.” And the first of these ads was a response to a sitcom that was hot—a decade ago. A sitcom, by the way, in which the nerd opposite Jerry always lost.

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