OPINION
Selling Windows 7: The Good, the Bad and the Tragically Hip

So Microsoft (Nasdaq: MSFT) has a new operating system. Can the company still make average computer users care?

By the time you read this, Windows will have officially launched, and there will probably be a new round of commercials for the operating system -- and the new touchscreen computers containing it -- filling the time between weekend NFL games and MLB playoff action on your TV. The Thursday press conference in New York starring CEO Steve Ballmer will have provided its share of sound bites and feature demonstrations for the cable business channels. Banner advertising will fill a host of Web sites. The reviews will start hitting the media outlets.

However, the original question still stands: In a Google (Nasdaq: GOOG) and Facebook-centric world -- where smartphones are the new notebook computers, Apple (Nasdaq: AAPL) has been the king of tech cool for eight years running, and the consumer has more power than ever -- can Microsoft still sell its products?

The computer industry is counting on it. Recession clouds may finally be lifting, and just like the good old days of the mid-'90s, new Windows-laden machines flying out the doors of Best Buy (NYSE: BBY) could help put some profits back in a lot of tech company bottom lines. For those of you who still get old media delivered to your doorstep, get ready to shake a colorful blizzard of consumer electronic store ad inserts out of your Sunday newspaper. (That scene in and of itself should tell you what kinds of obstacles Microsoft faces with Windows 7 -- the media and ad industries are shifting tectonically, but money will still be spent on loud, four-color newspulp selling Windows machines.)

I like Microsoft's chances, but only because Vista was deemed to be unworthy of an upgrade and Windows 7 is better. Also, anyone with an eye on buying a new computer will be taking a hard look at a sub-US$500 Windows netbook in these budget-conscious times. More businesses -- those scared off by Vista -- will probably upgrade those XP and Windows 2000 machines sitting in cubicles. And for God's sake, even in a tough year, has anybody checked to see how much cash Microsoft still has on hand? We're talking tens of billions, folks. Never count out a company like that.

But those buying decisions will all be based on price and convenience, and in all likelihood not some Microsoft commercial that breaks new ground in persuasive tactics. Kylie, the extremely cute yet annoyingly tech-savvy star of the company's first round of Windows 7 ads, won't be cited by customers as they leave their neighborhood electronics retailers with a new laptop in hand. She may, however, remind people to pick up that hot new Wii game for the kids.

When Microsoft Marketing Moved Mountains

Speaking of Windows 2000, fire up the wayback machine, because all this talk of software launches, marketing and press conferences is reminding me of February 2000 and the Moscone Convention Center in San Francisco.

Back then, Bill Gates and company still had the juice, even fresh from a spanking by the Clinton Administation's Justice Department. I had just interviewed Gates for CNBC and was hustling back to find a seat in the audience to catch the festivities -- and I mean festivities, because in 2000 a new Windows OS was still an "event," not just in the tech world but for business overall, for reasons mentioned above. It also meant money spent on hoopla, staging and celebrities. When Gates wasn't extolling the virtues of Windows 2000 and introducing various product managers for demonstrations, he was tossing to comedy skits featuring John O'Hurley, "Seinfeld's" Mr. Peterman.

The best part came at the end, when Gates mentioned something about Windows 2000 providing a smooth transition for computing into the 21st century. On cue, an entire section of the stage floor actually lifted up to unveil Carlos Santana and the opening notes of his then-hit, "Smooth." Now that was entertainment. And marketing muscle. And the clout of a groundbreaking tech company in its prime.

Santana's power-chords have long faded into memory, and now Apple (naturally) is the one bringing out the musical acts for new iPods, iPhones and all its iGear. The Vista launch nearly three years ago had its share of stunts as well, including the "human billboard" in Times Square and lots of butterfly-themed motifs at the 2007 Consumer Electronics Show in Las Vegas, but the bad reviews for the OS and the rapidly changing tech industry landscape soon eclipsed the marketing.

It's Square to Be Hip

So far, the television marketing for Windows 7 has tried to build off of the positive vibes that were engendered by the anti-Mac ads Microsoft commissioned earlier this year. They featureed a slew of supposedly real people visiting a store that looked an awful lot like a Best Buy -- where they sell both Macs and PCs -- and griping in voiceover about the high cost of Apple computers and the just-right price tags for Windows machines. Coming during the height of a recession, the ads struck the intended chord and actually did what was seemingly impossible: made Windows laptops look like computers "for the rest of us," in the famous words of Steve Jobs.

The Kylie ads continued the Apple-inspired themes by playing up multimedia functions that are so easy to use that this 6-year-old could manage to put together online scrapbooks featuring positive reviews of Windows 7, all set to the supremely cheesy '80s rock hit, Europe's "The Final Countdown." (If memories of an arena rock one-hit wonder band don't make you want to race out and buy a PC, then apparently nothing will). A different ad plays the theme song from another 1980's artifact, "The A Team," which starred Mr. T.

I pity the fool who doesn't get the connection here: The musical selections are designed to hit the key part of the temporal cortexes of the demographic now making computer-purchase decisions for homes and offices.

Which is why the "launch party" videos from Microsoft are now drawing lots of derisive laughter in Facebook update links nationwide. A Stepford Neighbors group of people load up snacks and drinks in a typical suburban kitchen, chattering away about how neat it would be for everyone to have their own get-together on the night before Windows 7's Oct. 22 launch. Many of my Facebook friends are wondering if Microsoft's ad agencies weren't shooting for "Saturday Night Live" commercial parody territory with this one, and ended up being too subtle and post-ironic for their own good.

The "Family Guy" tie-in episode set for Nov. 8 seems more in line with the intended target audience, but it also reeks of a company trying desperately to appear hip by linking itself to a show that regularly violates the good-taste line. (Keep Kylie locked in her room for this one, folks.)

Other ads coming soon will make it seem as if everybody who had complaints about Windows Vista was actually part of the mother of all beta testing groups for Windows 7 -- a potentially smart move, as long as the new OS delivers the goods.