What Were You Thinking, Microsoft?

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I wasn't the only one left scratching my head after the first of the Jerry Seinfeld ads for Microsoft (Nasdaq: MSFT) aired last night. Was the 90-second spot of Seinfeld and Bill Gates shopping for shoes supposed to be funny? Was it supposed to be informational? Was it supposed to be conversational? It only seems to have succeeded on that final point, because the blogs are ablaze with chatter over the eclectic ad this morning.

The ad certainly didn't go for the jugular. If anything, it was a nod to the very companies that the software giant is battling. The notion that computers will eventually become food? Is that subtly conceding the market to Apple (Nasdaq: AAPL)? The Conquistadors running tight? Is that a shot at its own fading dynasty or the passing of the baton to Google (Nasdaq: GOOG)? Gates as a platinum member of the Clown Club with his infamous mug shot to match? That almost got a chuckle, but what's the point?

There is nothing wrong with self-effacing humor, but how can you tackle the effective "I'm a Mac, I'm a PC" ads by pitching your products as delicious? This is the launch of a $300 million marketing campaign. The stakes are real. When you have Dell (Nasdaq: DELL) pitching $349 Linux-based Ubuntu-powered mini laptops this week, you don't "clown" around.

History may redeem Microsoft here. This offbeat ad may be the spark that turns Microsoft cool again, cutting down rivals like Apple and Google that are nibbling away at market share at Microsoft's expense in computing and cyberspace respectively. It certainly doesn't seem that way now, but Microsoft has had enough time to map out what should be a well-orchestrated campaign. Last night's ad isn't going to inspire Vista upgrades, but it is getting people to talk about Microsoft again.

It's a start. It's a strange start. OK, it's a bad start. But only Microsoft knows where this ends. The only thing for sure is that this will be a case study dissected by business schools once the campaign has run its course.

If the shoe fits, of course.