Technology's 10 Most Mortifying Moments

Tech history is full of moments that make you say 'ouch.' Check out our favorites, then cast your vote for the most mortifying moment of all.

We've all had excruciatingly embarrassing moments. We say something loud and inappropriate at a party and the room abruptly falls silent and stares. Or we misbutton our shirt and it takes half a day to figure out why everybody's giving us funny looks. That sort of thing.

For most of us, these mortifying moments pass quickly. But when they occur in the relentlessly interconnected world of technology, they spread through the Internet like a bad cold that won't go away.

Here are our nominations (in no particular order) for the 10 most mortifying moments in technology history. These aren't bad business decisions or introductions of lousy products (for those, see Don't Believe the Hype: The 21 Biggest Technology Flops).

Rather, they're incidents in which deep, red-faced embarrassment by specific individuals and companies was -- or should have been -- the order of the day. These are the moments when the technology world stops and stares.

After you've read our nominations, please help us pick tech's most mortifying moment by voting in our reader poll -- and let us know what embarrassing technology moments we missed in our comments area.

Let the Nominations Begin

Let's start our list with mortifying Microsoft moments. Oh, where to begin? There was the time Bill Gates obfuscated so severely at the DOJ vs. Microsoft antitrust trial that he made the judge laugh, and the time Gates, while demonstrating Windows Media Center, couldn't get a remote control to work while Conan O'Brien provided running commentary.

Or how about the photo of a very young Bill draped moony-eyed over a monitor? (Catch the embarrassing moments of two other well-known Silicon Valley figures on the same page.)

For our money, though, here are the three best Microsoft mortifiers:


Bill Gates Gets a BSOD


Windows 95 provided a much spiffier interface than its predecessor, Windows 3.1, but it was neither very feature-rich nor very stable. Microsoft promised that Windows 98 would be much more solid.

However, we should have gotten a clue about what the future of this operating system held when Gates' presentation at Comdex Spring in 1998 went seriously awry, ending in a very public BSOD (Blue Screen of Death).


Monkey Boy Runs Amok


Bill Gates might be the visionary behind Microsoft, but CEO Steve Ballmer has long been the suit behind the vision. So what got into this billionaire that made him dance around like, well, a monkey boy when coming on stage at a 2001 employee gathering?

Was he trying show he's more fun than Steve Jobs? Was it job stress? Had he joined a cult? We may never know.


Vista Has Trouble With


Speech Recognition

speech recognition gone awry

Bill Gates once predicted that speech recognition would someday equal the use of keyboards as a leading input technique. It seems, however, that we have a ways to go.

The technology has rarely been put in a worse light than in a nightmarish 2006 presentation of Windows Vista's speech-recognition capabilities, in which nearly every word spoken by a Microsoft executive came out wrong on-screen.

Although Gates and Co. seem to have had more than their share of embarrassing missteps, we'll stop picking on Microsoft now. To be perfectly fair, many other companies have had disastrous demos as well -- including the ultrahip Apple and its leader Steve Jobs. And demos are just the beginning -- there are plenty of other highly awkward moments in technology, as the rest of our list shows.

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