Note to Seinfeld: beware, Microsoft's made some bad TV ads

The comedian may need to find his inner Man of Steel if he's to succeed in changing the world's impression of Windows Vista.

We all know Jerry Seinfeld's into Superman. Now, the comedian may need to find his own inner Man of Steel if he's to succeed in changing the world's impression of Windows Vista.

Let me get you caught up: Seinfeld struck a deal to become the face of Microsoft's most expensive ad campaign ever. The goal, of course, is to undo the damage done by the bad rap Vista's gotten -- both from word-of-mouth and from that pesky Apple campaign portraying Windows as the outdated dork.

Rest assured, then, these new ads won't be about nothing. The $300 million campaign will center on the slogan "Windows, Not Walls." Seinfeld will appear with Microsoft Chairman Bill Gates in the spots, securing a cool $10 million for his time -- and, Microsoft hopes, giving its struggling software a new start.

Seinfeld may be ad-worthy, but he has a big task ahead of him. We thought we'd take a look back at his predecessors to see what it truly takes to master Microsoft's domain. With that, I present the Top 10 Most Memorable Microsoft Ads of All Time. And by "memorable," I don't always mean good. Get ready to laugh.

1. MicroSex Talk about targeted marketing. This XP ad shows a guy struggling to get his girl's bra off -- then, like magic, Windows shows up to save the day. If only he had the password...

2. Oh-So-Eighties Current chairman Steve Ballmer is way too excited in this very-80s ad for Windows 1.0. Highlights: The plaid jacket, the Miami Vice references, and the touting of Microsoft Paint's awesome power. We can only hope this thing never actually made it on-the-air.

3. He's Baaack... Apparently, Ballmer didn't bomb enough with the 1.0 push, so he came back for an encore performance with XP's introduction a decade-and-a-half later. Maybe Jerry can get some pointers from this gem of an ad.

4. Lost in Translation This Japanese ad for Windows 3.1 may leave you feeling more frightened than inspired, but the weird little guy yelling into the camera at the end is priceless. If Jerry remakes this, I will break down and buy Vista.

5. Yo! MS Raps Watch out, Puff Daddy: The DOS rap crew is ready to drop a beat on your C prompt. This video appears to be some kind of promotion for the groundbreaking DOS 5.0 upgrade, which -- ready for this? -- features an "undelete" feature! (Warning: While watching this commercial may bring back memories, it may also make you cringe, cry, or strike yourself repeatedly with a blunt object.)

6. Why Vista Didn't Succeed This spot -- said to be an internal promotional video for Vista SP1 -- may explain why Vista never caught on. Enough said.

7. The Bad Breaker-Upper Here's one our old pal Elaine might appreciate. A woman spends a full minute going through a long-winded breakup speech with her computer, seemingly because it came from a "secondary PC market." Yadda, yadda....yadda.

8. The Moneymaker Get Windows and get rich -- at least, that's what the woman in this Australian commercial from the mid-90s seems to think might happen. You know, my cousin Jeffrey works for the Parks Department and makes a very good living. Maybe I'll set the two of them up.

.9. Animal Act What's the deal with animals in advertisements? Seinfeld will have to stand up to the legacy left by this rabbit in the Microsoft spokesperson hall of fame. This furry fella sure knows a lot about using Office, too. Advantage rabbit

10. The Psychic Spot Our final entry seemed to have a psychic sense of the struggles to come. The ad, for an early version of Office, says: "It never starts out brilliant. It starts out ridiculed because it's different." Hey, maybe Microsoft can just reuse this concept and tack a five-second Seinfeld appearance onto the end. "I'm Jerry Seinfeld, and I approve this message."

Looking back on the past, one thing's for sure: Jerry has his work cut out for him to go out on a high note this go-round. Let's hope he doesn't have to look for a job at Vandelay Industries by the time it's all over.

By the way, for what it's worth, our comedian compadre had a Mac in the back corner of his apartment throughout his show's nine seasons. Not that there's anything wrong with that.

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JR Raphael

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