The 10 Most Uncool Moments in Tech - CIO.com - Business Technology Leadership

PC World — 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.

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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 "I'm 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 realize 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."

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