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Microsoft Fails at the Worst Possible Time

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Two years ago, Apple (AAPL) was wiping egg off its face.

Months before it unveiled the much-ballyhooed iPhone 4, Cupertino had the wind sucked from its sails when a prototype of the device fell into the hands of Gizmodo, which promptly reviewed the design and spoiled much of the surprise.

So as Steve Jobs took the stage, he was already covering familiar ground. But something even worse occurred during the presentation: The device he was demoing failed. Perhaps a precursor to the widely publicized Antennagate, or it truly was too many bloggers flooding the convention's Wi-Fi, it was the worst time for Apple to suffer another embarrassing blow. (Though when Steve asked for a solution and an attendee shouted "Verizon (VZ)!" that was pretty hilarious.)

Glitches during keynotes and product launches are like the original British version of The Office: chock-full of squirming hilarity.

There was Sony's (SNE) Wonderbook hiccups at E3 earlier this month. The first day of Google's (GOOG) I/O conference last year went completely black as the keynote stream went down for most of the day. And the sweaty "Developers! Developers! Developers!" chant given by Microsoft (MSFT) chief Steve Ballmer was enough of a misstep to qualify as a technical gaffe.

And while Redmond continued that cringing tradition with its bizarre final presentation at this year's CES convention, its grand introduction of the Surface tablet had an even bigger fail just as it was attempting to prove it could go toe-to-toe with the iPad.

As Steven Sinofsky, president of the Windows division at Microsoft, was demonstrating the versatility of the device and tried to run Internet Explorer, the Surface froze -- right around the time Sinofsky says, "I can browse smoothly," and "I can have a great experience just with browsing."

Still, it's not as embarrassing as ASUS' Jonney Shih introducing the Padfone.

(See also: BlackBerry Deemed 'Coolest Brand' in Shocking Survey and iPhone Can't Match Android's Versatility, Says Steve Wozniak)

Twitter: @mcs212
POSITION:  No positions in stocks mentioned.