The big news in the blogosphere today involves new details about Microsoft’s upcoming $300 million Windows ad campaign: It will apparently feature Bill Gates and Jerry Seinfeld, use the slogan “Windows, Not Walls,” and begin on September 4th. I’m not a professional ad critic, and I can’t even play amateur critic before I’ve seen the ads in question. But I can’t stop my mind from racing ahead, either.

So without any further ado, lemme throw out ten initial questions, impressions, and reflections about the campaign and Windows marketing in general–all of which are subject to revision and retraction once the ads hit the airwaves in a couple of weeks.

1. Bill Gates is doing Microsoft ads? The noted philanthropist? Didn’t he used to work there or something? It’s fascinating to see Microsoft come back to him as the public face of the company –it’s only been two months since all the tearful, nostalgic fuss about him passing on the torch.

2. Okay, it’s completely understandable why they’d decide to put Gates in Vista ads-he remains the human personification of Microsoft. Unless you can envision a Windows ad campaign built around, say, Steve Ballmer.
Er, actually, we already know what that would look like:

(Full disclosure: I like that video so much I just watched it three times…by choice! Wouldn’t rerunning it cost less than $300 million?)

3. But it’s still surprising to see Gates back so quickly. You gotta think that it’s absolutely mandatory that Microsoft being to to position Windows as part of the future of computing, not a legacy of the old way of doing things. The company would bristle at what I’m about to say, I’m sure, but Bill Gates is a representative of the past–more than even since his retirement. Long term, you gotta think it’s in Microsoft’s best interest to position itself as a company that’s vibrant, relevant, and forward-looking sans Gates.

4. Seinfeld? The Bee Movie guy? The husband of that cookbook author? The fellow whose sitcom (1989-1998, RIP) dates from the heyday of Windows 95? (Correction: When the show premiered, the current version of Windows was 2.0!) Again, it’s odd to see Vista associated with someone who’s most famous as the leading comedian of a previous era. Not that there’s anything wrong with that.

5. How big a problem is it that Jerry–at least the fictional Jerry on his show–was famously a Mac user? Does that affect the credibility of his pitch? Did he switch allegiances for an easy $10 million? Did he actually move to a PC in, say, 2001 or thereabouts, but nobody noticed? Is the whole question moot, since no rational person would choose an operating system because a famous comedian told them to?

6. Maybe tying Vista to the past is intentional, or at least shows Microsoft’s subconscious at work. I get the sense sometimes that Microsoft gets exceptionally wistful when it looks back at the Windows 95 launch. It’s certainly the best example of the company engaging in massive, massively successful hoopla. Perhaps that’s why the company is apparently associating Windows circa 2008 with a couple of guys whose fame arguably maxed out in the mid-1990s

7. Ultimately, I kinda think that Microsoft and celebrity spokespeople don’t mix very well. At least not in any way that involves any celeb hipness rubbing off on its products. Oftentimes the company goes with the safest, least imaginative possible option–Jay Leno, Regis Philbin, and Conan O’Brien have all been involved with Windows launches. Other times, no particular rhyme or reason seems to be at work: I went to a 2004 Windows Media Center event with Queen Latifah, and she was fun and engaging…but  it didn’t seem to be clear to anyone involved what she was doing sharing a couch with Bill Gates.

8. Hey, time out for a couple more videos! They both involve Bill Gates, celebrity guests, and misbehaving Windows demos! Fiest, let’s watch Regis attempt to contact Bill via a glitchy Webcam at the 2001 Windows XP launch in New York (I shot this video myself)…

It’ll be interesting to see if Seinfeld’s Windows testimonial can top Reege’s: “It really knocks you out–I guess the people who are more familiar with it are really impressed, and I am too, but I must tell you–there’s a lot to learn. But it’s easier this time to learn.”

Now here are Bill, Conan, and a balky Windows Media Center at the 2005 Consumer Electronics show.

9. “Windows, Not Walls?” It’s hard to gauge what that slogan means until you see the ads. (That may not be a good sign: Maxwell House doesn’t need to explain “Good to the Last Drop” to anybody.) At first blush, it sounds a little geeky. What are the walls? Who erected them? Apple? The Web? Do normal people worry about technological walls, or know what they are?

10. Obvious knee-jerk response to the slogan: Microsoft spent years building walls all around its products. It attempted to lock people into using Internet Explorer. It released Office upgrades with new file formats that made it hard to work with users of previous versions of Office, let alone other suites. For years, it seemed to work. These days it doesn’t. But when I think of Windows, I don’t think of it as an alternative to walls. I think of it imprisoning users within them.

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