Apple's "Mac vs. PC" ads are advertising legend now, and in 30 seconds can do more to spotlight the differences between Apple and Microsoft than just about anything else.

So effective, they even annoyed Bill Gates, who says when he first saw them, he didn't get them; didn't understand them.

Apple's

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[AAPL  Loading...      ()   ] ads are almost appointment television: you move a little closer to the screen, you turn up the volume a little more. They just work.
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Apple: CNBC Intelligence

- Fast Money's Take on Apple

- Jim Cramer: Play Apple -- Carefully

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And all the while, Microsoft

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[MSFT  Loading...      ()   ] investors and fans have been waiting for the company to answer. To come up with something that takes a swipe back. For Microsoft to fight back.

And for years, Microsoft has been silent. Quietly letting Apple paint its opponent. Control the message. And it has been working. Mac sales are soaring, Microsoft shares have gone nowhere, and Vista is largely viewed as a dog. And not a cute puppy, but a dog that doesn't perform.

Apple has owned the message.

So imagine Madison Avenue's surprise when The Wall Street Journal reported today that Microsoft will embark on a $300 million image campaign for Vista, and use comedian Jerry Seinfeld as its pitchman, paying him a reported $10 million for the gig.

If anything shows how Microsoft still doesn't get it, it's this quizzical move. Why in the world would a company trying to blunt the coolness factor from Apple choose a comedian-turned-professional-pitchman (see Jerry's American Express commercials) as the face of Vista? I'd get it if this were ten years ago and Seinfeld was at the height of his popularity.

But he's spent his years post-"Seinfeld" (the show) doing occasional standup, the "Bee Movie," some other little projects here and there that may or may not generate revenue -- and largely living off the spectacular residuals his one great idea, his TV show, generated.

Kind of like Microsoft itself: it comes up with a blockbuster operating system and then spends the rest of its time living off the residuals. So I suppose in that respect, I get the choice here. (Oh, and Seinfeld's a professional kvetcher and complainer, so I guess as a spokesman for Vista he has a lot in common with so many of the software's users. But I digress.)

The Journal says Microsoft considered Will Ferrell and Chris Rock too. Either would have been far better choices. What about Will Smith? Jack Black? Geez, Jeremy Piven or Kevin Spacey? Patrick Dempsey? Somebody cool. Relevant. Edgy. Fun.

Instead, Microsoft makes the safe choice; the one that might seem to be the least disagreeable.

Which is unfortunate. You want to generate emotion. Go on the offensive. Get your story told in a compelling, captivating way that generates business and shuts down the competition. I just can't see Jerry Seinfeld, at this stage in his career, being the effective face Microsoft hopes he can be.

But I certainly can see a new set of "Mac vs. PC" ads:

Mac: "Hello, I'm a Mac."
PC: "And I'm a PC. As in Politically Correct!"
Mac: "What's up PC?"
PC: "Nothing, just making sure that I'm as inoffensive as I can possibly be so I don't make anybody angry and scare them away from buying me."
Mac: "Well, some might say buggy software that doesn't do what it promises is kind of offensive."
PC: "Yada, yada, yada."

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- eBay

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