You Vista Vista'd Over The Best Part!

Microsoft wants to be funny like Apple, and it's going to pay Jerry Seinfeld $10 million to help out, the Wall Street Journal reports.

According to the Journal, new ads for Windows Vista featuring Seinfeld will focus on connecting people and ideas using some form of the phrase "Windows, Not Walls."

That's a better catch phrase than anything we came up with piggybacking off Seinfeld's eponymous show: "This operating system is making me thirsty"?; "Helllloooo, APPLE"?; "No boot for you!"? We've got nothing.

Why Jerry Seinfeld was chosen to fight back against Apple's 'Mac vs. PC' ads on behalf of Microsoft isn't exactly clear. The software company wants to shed its stiff, stale brand image, yet Seinfeld's trademark humor is curmudgeonly and pessimistic. Not to mention the fact that he has already appeared in an Apple ad aired after his show's final episode.

Seinfeld has wide name recognition, but if Microsoft is looking to appear "cool" and "with it" with a younger crowd, Jerry Seinfeld is not going to do the trick. His sitcom ended in 1998 and since then he's done little besides voice and write Dreamworks' Bee Movie last year. Twenty-somethings view him is a comedic old-timer and prefer the likes of Seth Rogen and Steve Carell.

Seinfeld might have been a better choice for Microsoft in, say, 1998, when he was in the prime of his career -- that's when American Express picked him up for a string of commercials in which he appears opposite Superman. But since then, America Express has moved on to more current comedians like Tina Fey and Ellen DeGeneres.

Even if Microsoft had managed to snag a currently hot commodity like Steve Carell, at the end of the day, when has a stand-up comedian ever been used by a "hip" brand? Dennis Miller pitched for Net Zero, Bill Cosby for Jell-O, Don Rickles for Glad Bags, and Chevy Chase for Doritos. Those brands neither started out cool, nor became cool in the process.

Our one cause for hope is that producing the work for Microsoft is Crispin Porter + Bogusky, a cutting edge agency which has turned out fresh and entertaining spots for Burger King, Coke Zero, and Volkswagen. So hopefully, they know what they're doing.

Liz Gunnison