Can You Really Buy "Hip"?

Microsoft is getting lots of press about its $300M campaign to fix the Vista public image. My first thought is, "Why not spend $300M to fix Vista?" I have to admit I haven't used it much but there are no shortage of web reports by Windows enthusiasts panning it. I do know a few of the guys in the Microsoft Mac business unit and they seem to me like stand up guys trying to make a good product. Then again, they work on Macs.

Regardless, part of this campaign involves paying $10M to Jerry Seinfeld to pitch Windows along side that famous straight man, Bill Gates. This just seems wrong to me on so many levels. First, let me say as someone who has never met either man, I generally like and respect both Jerry and Bill. However, I don't see them making much of a difference for Visata's problem. From my very casual sideline seat, it seems to me that Microsoft is really losing this battle on the college campuses and 20-somethings. If they really wanted to stop the avalanche of switchers, they should use somebody younger than a 90's sitcom star (where his character always used Macs) and a retired CEO. Also, even if you could buy "hip", are these guys really selling it? Maybe I will be proven wrong but I'm already thinking these commercials are going to do more harm than good to Microsoft.