While reading other blogs and news sites on the announcement that Jerry Seinfield will be appearing in future Microsoft Vista ads, I particularly enjoyed Computerworld's Ten Reasons Why the Seinfeld-Microsoft Partnership Doesn't Work .
Here is reason one: There are eight seasons of Seinfeld out there with a Macintosh sitting on the corner of his desk. It will be hard to convince people he's switched to Windows Vista with all of that legacy Mac cred - especially now that Macs are gaining ground on Windows.
The whole thing has "I will do anything for enough money" stamped all over it, and I just don't believe that is going to help Microsoft's credibility, much less rehabilitate Vista's poor public image. When you have to bribe pay one of your competitor's high-profile users to shill for your own product, it is nothing more than perfuming the hog.
Also, I have viewed Apple's newest "I'm A Mac" commercials, and they are perfectly positioned preemptively in an area that Microsoft is likely to strike: it is too hard to switch.
For example, here are the "PC's" theme statements in two of these commercials:
Off the Air: Fear of switching is the foundation of customer loyalty for PCs.
Throne: Vista is something of a hassle, but switching computers is an even bigger hassle.
Of course "Mac" counters this by emphasizing that Apple store employees can move a new user's data easily over to a Mac for free so that switching is actually easy. Also, having a cute Mac genius explain this in one of the commercials certainly doesn't hurt.