Technology's 10 Most Mortifying Moments

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).

Bill gates gets a BSOD.

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 Peach 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.


IBM Exec Inflates Resume

Jeff Papows' tenure as head of IBM's Lotus Development division was successful from a business standpoint, but in 1999 it emerged that he had falsified his resume and made some less-than-truthful claims to co-workers through the years. Instead of being a Marine captain and a heroic jet fighter pilot, he was a lieutenant air-traffic controller. Rather than a Ph.D. from a prestigious university, he had a degree from a correspondence school. And it turns out he wasn't really an orphan after all.

With an upper lip apparently made of steel, Papows refused to be publicly embarrassed, claiming that the errors were the result of water cooler talk that took on a life of its own. Nor was IBM particularly mortified, allowing Papows to stay on the job until he resigned in 2000 to lead an Internet start-up.


iPhone Bills Kill Trees

If the iPhone had been introduced a few thousand years ago, it would have been carried into the capital city on a palanquin and those en route would have prostrated themselves until it passed.

Fortunately for those who rebel against that sort of pomp, there were also a few embarrassing moments for Apple, such as when the company eliminated its 4GB model and cut the price of the 8GB model by $200 just two months after the devices had launched. Even ardent fanboys and girls used language that was so surprisingly sharp that Apple agreed to give early adopters a $100 store credit.

But the most embarrassing iPhone moment came at the expense of the device's U.S. cellular carrier, AT&T Inc. The company's extraordinarily detailed billing process resulted in some users receiving bills this August that ran dozens or even hundreds of pages long, as captured in blogger Justine Ezarik's video of her unwrapping a 300-page phone bill. (It came in a box.)

300-page iPhone bill

Without actually admitting embarrassment, AT&T said it would start sending out more svelte bills to iPhone users.


Kid Cracks Porn Filter

It goes without saying that it's a good thing to protect our children from pornography and other unsavory elements available on the Internet. So who could blame the Australian government for a project that would provide a so-called porn filter to parents?

The problem was that the software, released in August of this year, cost $84 million -- and that a 16-year-old Melbourne boy, Tom Wood by name, cracked the filter in about 30 minutes. Young Tom's assessment: "It's a horrible waste of money."

A federal official responded by saying that the government knew all along that some kid would come along and crack the scheme and that "the vendor is investigating the matter as a priority."


Sony Hacks Its Customers' PCs

Cynics will tell you that the recording industry is paranoid and slow to enter the digital age. The industry insists it is merely trying to ensure its artists are fairly compensated.

But Sony BMG came down squarely on the side of paranoia in 2005 when, in the name of copy protection, it placed invasive rootkit software on an estimated 15 million music CDs by more than 100 artists. When a CD owner put one of these CDs in a PC drive, the software was automatically installed on the computer without the user's knowledge. Perhaps this system provided copy protection, but it also opened the user's computer to various types of spyware, malware and other nuisances.

A number of users and states sued the bejabbers out of Sony, which paid out big bucks to settle the matter. Apparently Sony wasn't too embarrassed, though -- it recently pulled the same stunt again, this time placing rootkits on USB drives it was selling.


Tech Reporter Reveals Too Much

Many of us have had nightmares about being out in public without our clothes on. So you can only feel for somebody when that really happens, as it did in a virtual sort of way to TechTV reporter Cat Schwartz in 2003.

The gist of the story is that Schwartz had a photographer take provocative pictures of her. The pictures were taken while she was topless, but she cropped the images to be more modest and posted them online.

Cat Schwartz

The problem was that she didn't realize how Photoshop, or possibly the camera itself, included the original image as a viewable preview of the cropped image. Not surprisingly, this mistake spread around the Web rapidly, giving Cat Schwartz an additional 15 minutes of fame, or at least of mortification.


NSA Offspring Cripples the Internet

Let's take a trip down memory lane, back to 1988. This was a time when widespread security threats were starting to become known, but we hadn't yet reached our current hypervigilant state. That's also when a Cornell student, Robert Morris, Jr., released what many believe was the first major worm to be spread via the Internet. He claimed it was a relatively innocent exercise.

The so-called Morris worm brought down a big chunk of the Internet. Of course, in those days the Internet was a relatively small network, largely limited to academics and the military establishment, so the worm didn't do nearly as much damage as it would today. Still, it caused, by some estimates, $15 million in damage. Morris apologized for releasing the worm, was convicted and received probation.

Now the truly embarrassing part: Morris' father, Robert Sr., was a well-known, highly regarded security expert who worked for the National Security Agency. However, while Dad was undoubtedly mortified at the time, he surely must be proud of his progeny, who is now a professor at MIT.


Just About Everybody Shines Up Their Wikipedia Write-ups

What do Microsoft, the Vatican, the FBI, Al Jazeera, Exxon Mobil and Amnesty International have in common? They -- and many other organizations with household names -- have been busted for altering Wikipedia entries that don't flatter them.

To read more please read this article