Microsoft’s hiring of Jerry Seinfeld to do a new line of commercials seemed strange, and most “tech news pundits” seemed to have the same conclusion. I like Seinfeld, but he’s kind of “1990s cool,” which is exactly what Microsoft doesn’t want to be seen as when Apple’s done tremendously well at painting them as yesterday’s technology, and as someone who tries, almost pathetically, to seem hip.

I’m still not terribly sure why they picked Seinfeld, actually, but I just watched the ad, and have to agree with CNET’s Reality Check: I might not go so far as to call it “superb,” but I don’t think it was bad. And kind of like what I just got done saying in the comments elsewhere about Chrome, this ad isn’t the “final product.” It’s a first step.

It’s admittedly a little weird. But Microsoft’s marketing department is no stranger to running ads that people don’t get or are just downright bizarre. Seinfeld is walking around a mall eating a churro, when he walks into a shoe store and sees Bill Gates trying on shoes. (Later, Bill is eating a churro, too.) Seinfeld walks in and appears to push aside the salesman, giving Bill Gates much better information about the shoes. As he’s talking, a Hispanic family comes up to the window and comments on the shoes in Spanish, saying the same things about the shoes as did Seinfeld. (Via the subtitles.) The two chat for a while, and at the very end, Seinfeld complains about his computer and asks Bill if they’re ever going to come out with something that works. (Err, without the negative overtones that my sentence gives it.) He tells Bill to “adjust his shorts” (I think that’s what he says?) as a signal if they are. And then… Bill Gates appears to wiggle his butt in response. Many have called this fairly disturbing.

Despite the fact that the ad is pretty weird and barely talks about Vista, I’m not sure that means it’s a total failure. A few thoughts:

• If Microsoft came out with an ad in which Jerry Seinfeld stood around talking about the great features of Vista, it probably would have been a failure. You maybe could have made it a little bit funny, and worked in some jabs at Apple. But I think it would have been viewed as trying to copy the Mac vs. PC ads. And frankly, hearing a listing of Vista’s features would probably be boring.
• The hard sell, in my opinion, is a bad idea anyway. When was the last time you saw an ad for Coke that talked about its preferable flavor?
• In a way, I think it’s just the sort of “maintenance marketing” that companies at the top of their fields can get away with. For a long time, Apple dominated ads, and seemed to become more and more popular. Meanwhile, we didn’t really hear much of anything from Microsoft. It almost seemed like Microsoft was sinking while Apple grew. So I think another thing this ad accomplishes is just reminding us that Microsoft’s still in the game. If I was an investor, I’d be very happy.
• The oddness, although, well, odd, drew me in. Why is Bill Gates at a shoe store? Why is Jerry Seinfeld eating a churro while wandering around a mall by himself? Why is Jerry apparently an expert on shoes, and why does Jerry take over the sale of the shoes for Bill? Why is Bill Gates depicted as shopping at a budget shoe store anyway? Why is there a Hispanic family, speaking in Spanish, talking about the shoe Bill Gates is buying? And, more importantly, what does any of this have to do with Windows, or even Microsoft? It’s almost a little bit of mystery and suspense. They could have tried to answer some of those questions, perhaps, but they got me to watch it. Twice.
• People seem to have a tendency to view Microsoft as an evil corporation. Besides the fact that Apple doesn’t have too many people who think it’s evil (though it definitely has some, and I think it’s a growing crowd), they also have the advantage that Steve Jobs is a very prominent, fairly-likable spokesperson. So the involvement of Bill Gates, I think, was actually a brilliant move. Especially because it turns out that Bill Gates is a pretty charismatic guy. I’m not terribly sure why, but some quality about him almost reminds me of Mr. Rogers. Especially in this ad, he comes across as someone we can relate to, and someone who’s pretty friendly. The ad wasn’t about boosting his image, of course, though it definitely does. But in doing so, I think it puts a face to Microsoft. (And a positive one, at that!) They’re not an evil corporation, but instead, they’re friends of Bill Gates, who buys shoes at a discount shoe store in the mall, eats churros, hangs out with Jerry Seinfeld, and works on improving computers for you and I. I think this is where it succeeds the most.
• There’s a bit of humor. It’s hardly as funny as Cake Wrecks or Borat, but intense humor doesn’t belong in an ad. But you get a little bit of Seinfeld’s quirkily-humorous personality, mixed with a little bit of a good-natured humor about Gates: like when he presents his discount card, proudly mentioning that it’s a Platinum card, and when you see that it bears a goofy picture of him about the time he started Microsoft.
• It’s (presumably) the first of a series. I have a hunch they were more just trying to “introduce” Gates and Seinfeld as characters in this one, and that subsequent ads will at least make passing references to Microsoft and Vista.