The 10 Most Uncool Moments in Tech

4. Bill Gates Goes for Laughs

What's the deal with that Microsoft-Seinfeld ad campaign? In what was easily one of the most bizarre moves in tech advertising, Microsoft spent $300 million on a short-lived series of commercials featuring Jerry Seinfeld and Bill Gates in 2008. The idea, Microsoft said, was to help "engage consumers in a conversation" and "create an emotional connection."

That connection started with a two-minute ad showing the odd couple eating churros and shopping for shoes.

Now, for the record, I thought this ad and its equally strange sequel were hilarious. But not everyone got the joke. A critic in AdWeek called the campaign "beyond bizarre," saying it "[shot] itself in Bill's size 10 Conquistadors several times." Computerworld's Preston Gralla wondered whether the spot was the "worst TV ad ever."

There may have been something to those ads about nothing, but it didn't last for long: Microsoft quietly put the kibosh on the concept after only two commercials, opting to move its campaign in a slightly less abstract direction. Not that there's anything wrong with that.

5. MC Clueless Drops a Beat

When it comes to creating clueless concepts, no one does it better--or worse, I should probably say--than the folks at the Software and Information Industry Association. The SIIA, as the organization's called, is perhaps best known for its jaw-droppingly bad early-90s rap video, "Don't Copy That Floppy."

The nearly 10-minute clip features a character named "MC DP" (that's "Disk Protector") and is loaded with more cheese than you'd find in a freshly nuked Hot Pocket. Don't take my word for it--watch for yourself.

"Don't Copy That Floppy" was rough enough, but the SIIA didn't stop there: The group came back in 2009 with an updated version of its anthem, "Don't Copy That 2." MC DP (this time, it's "Digital Protector") revises his rhyme to cover more modern forms of copyright violation. The technology may have changed, but DP's M.O. is the same: trying to convince America's youth that sharing files will result in fines and jail time.

Just wait for 2012, when MC DP releases his next teen-targeted single: "Don't Copy That Floppy, Smoke Cigarettes, Do Drugs, Drink, or Engage In Premarital Sexual Relations (All of Those Things Will Send You To Jail or Kill You)!"*

* Just kidding.**

** I hope.

6. Apple Goes to School

Regardless of what you think of its products, it's hard to deny Apple is brilliant at marketing. But the Cupertino crew didn't always have the magic touch.

Back in the mid-80s, Apple put out an ad for its Apple IIc computer. The spot, about a teenager's high-school nightmare, is misguided enough to leave anyone in a cold sweat.

At least we know if this whole tech thing ever turns sour, Apple has a bright future producing after-school specials.

7. Packard Bell Learns a Lesson

In the mid-90s, Packard Bell tried to jump on the cool train with an ad likening the outside world to some sort of post-apocalyptic jungle. Downtrodden humans push cars and walk over bridges in mindless unison. At the center of it all sits the public library, a run-down old relic with red-uniformed guards who march around shushing everyone in sight.

The ad's message: Why subject yourself to this kind of hell when you could stay at home and do everything from your Packard Bell computer?

The message, suffice it to say, failed to land (though it may have given that kid from Apple's ad a few new nightmares). In the end, the only thing that looked dated and out-of-touch was Packard Bell itself.

Next: Microsoft parties down with Windows 7

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