So... MSFT are desperate, but although this feels like a desperation move to me as well, I don't know if it's entirely fair to say that hiring Jerry Seinfeld is an act of desperation in and of itself.
Microsoft's "name" comes (came?) from reliability in the business industry, where code you wrote almost two decades ago DOS 5 would run on Windows XP today (assuming you used their APIs for everything). Windows 2000 was a fast, snappy, and efficient OS that got the job done. Windows XP has a bit more "homey" but as the years passed and the service packs came in, it grew to fit that same role.
Windows has never been advertised as a truly "fun" OS until Vista's "the WOW starts now" campaign; unfortunately, I get the feeling that they're turning to the hip crowd because they've failed to stand out in any other way. From performance to reliability, Vista has flopped (I'm using it now, fulltime) - so they're looking for anything else that may save them some face.
So while it's no biggie for Apple to start advertising through Sienfeld, it is for Microsoft who have never been the sort of people to do this kind of thing.
Mac vs PC is not a symmetric fight.
If apple wins 1% of windows users, its a big win (somewhere around 10% increase in sales). But it doesn't work both ways. If windows 'steals' 25% of mac users, it's less then a 2% increase in windows sales. (& reaching those markets with airtime costs the same)
Windows could have beaten that just by reducing replacement time by a few months.
Going after Apple's (tiny) market, with their hands tied (Vista isn't fun) for meagre rewards isn't smart.
Microsoft probably benefits from low volatility in the market, while Apple and Linux benefit from high volatility.
And Microsoft's name... Well... They did have some fine products in the 80s.
If there's one surefire way to convince everyone Vista is cool, cutting edge and not liable to get frazzled by life's minor complications, it's hiring a 1990s sitcom star and professional kvetcher! Who, um, very visibly owned a series of Macs on his show.
http://gawker.com/5039828/mac+loving-seinfeld-endorsing-micr...
This reminded me of something that happens with tired regularity in advertising: Company executives hire the spokespersons that they identify with, instead of the spokespersons their customers identify with, because it gives them a thrill to brag that so-and-so endorses their product.
Another distinct possibility is that Microsoft knows exactly what they are doing, which is appealing to an older segment of the market, perhaps the IT managers that dictate corporate standards.
We may laugh, but they may be acting reasonably.
I mean, it's an OS, not a gaming console. I don't want it to be funny, hip, cool, or otherwise "in" - if that's what I had wanted I'd have switched to Mac a long time ago. What I want is an OS that... works. But it seems that I'm asking for too much, so now I'm stuck between a rock and a hard place (win32 systems developer, who really prefers Ubuntu as an OS).