The 10 most uncool moments in tech

From cringeworthy rapping to crazy on-stage antics, tech companies sure have made some big marketing blunders.

By JR Raphael / Wednesday, June 30 2010

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That Jeff Lebowski was one cool dude. Aside from the fact that he actually referred to himself as "The Dude," the iconic character from The Big Lebowski just had something about him--a kind of pure coolness that's hard to describe.

His secret? He didn't try.

Tech companies, on the other hand, try with all their might to come across as cool. Sometimes, they succeed--Apple's "Get a Mac" ads managed to project an air of coolness that stuck for years--but equally often, their attempts to connect with consumers make them look more out of touch than Mr. Magoo at a Megadeath concert.

Ultimately, it all comes down to something I call "The Dude principle of coolness": If you're actually trying, odds are, you're failing. And the harder you try, the greater those odds become.

Here are 10 times when tech companies' attempts failed miserably.

1. MSI takes a crack at viral video

MSI tried to hop on the pop culture bandwagon with this astoundingly disturbing video published to the Net in 2009. The clip shows a couple of guys in Spandex onesies (strike one) throwing laptops at each other (strike two) and catching them in certain unmentionable crevices (strike three...you're out!).

Take a look: MSI's concept, from what I can best surmise, was to show off the superthin profile of its new X-Slim laptops. And given the popularity of shows like MTV's "Jackass," you can see how a team of suit-wearing hacks might have seen the stunt as a cheeky way (so to speak) of grabbing college kids' attention.

What MSI failed to realise was that there's a difference between making people cringe and making them want to buy your product. This asinine stunt fails to accomplish the latter--no ifs, ands, or butts about it.

2. Sony gets a bad rap

Talk about a flop: Sony's 2006 attempt at connecting with the "cool kids" was so bad, the company actually had to apologize.

Remember this one? Sony hired a marketing company to create what was supposed to look like a teenager's blog. That "teenager," of course, was an employee who blogged exclusively about how he and his pals really wanted a Sony PlayStation Portable for Christmas.

The crowning moment came when a video surfaced showing the blogger's "cousin" Pete rapping about the PSP. Pete's lyrics included such insightful prose as: "Games so crazy / they totally amaze me / gotta ask my mom for one / fo' shizzy."

Savvy web surfers soon discovered that the blog's domain--Alliwantforxmasisapsp.com--was registered to an agency called Zipatoni. And then, everything fell apart.

Sony posted a note on the site admitting it was behind the effort. Days later, the blog and all the videos magically disappeared (hint: you can still see them via archive.org). In a statement made to BusinessWeek, then-Sony PR boss David Karraker called the concept "a marketing idea that was poorly executed."

Poorly executed, eh? As Cousin Pete might say, "fo' shizzy."

3. Microsoft gets musical

For a different type of musical disaster, we turn to our always-reliable friends over at Microsoft (who, as you'll soon see, make this list three times). In 2009, the gang from Redmond created a four-minute video promoting their new Songsmith software. The software lets you sing along with customized backing tracks while recording your best "American Idol"-esque efforts.

The video, unfortunately, came across more like a bad sketch than anything. Entertainment blog Videogum hit the nail on the head when it said it was like Microsoft had "found some kind of home-schooling Christian commune in the woods and hired them to make their commercial."

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." US 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.

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