The company, whose recent quarterly profit growth has been upstaged by Apple, is hoping that the 54-year-old comedian will help make Windows seem less stale and outdated. But the choice of Mr. Seinfeld--who is most associated with his eponymous, and quintessentially '90s, New York-based sitcom--has left more than a few industry observers scratching their heads, especially since Mr. Seinfeld will reportedly appear in ads with 52-year-old Microsoft chairman Bill Gates. After all, there is a reason Steve Jobs recruited Drew Barrymore's ex-hottie Justin Long to be the cool young Mac representative, and glasses-wearing author John Hodgman as the uncool PC, in the "I'm a Mac, I'm a PC" ads, rather than appearing in any ads himself.

The campaign was conceived by Crispin Porter + Bogusky, a Miami-based ad agency recently hired by Microsoft to redefine its image. The new ads are expected to premiere Sept. 4 and will use a variation of the slogan "Windows, Not Walls," according to several people close to the deal that the WSJ was able to reach off the record. Also considered for the ads were comedians Will Ferrell and Chris Rock.

Robert Passikoff, the president of the New York branding firm Brand Keys, said of Microsoft, "They are not seen as cool. Apple is cool. Can anyone even recall a Microsoft ad? No."

From the article:

At least they knew what they wanted.