The 13 Most Embarrassing Web Moments

We’re probably all guilty of the occasional Web slip-up. Instead of IM-ing your coworker to complain about your wife, you get mixed up and IM your wife herself. Or instead of forwarding that note from the boss–along with a snarky comment–to your friend, you hit reply. Or for a quick hit of mortification, just take a look at your MySpace page.

Those little missteps, alas, are trifles compared with the most embarrassing incidents on the Web.

Hoping not to embarrass ourselves, we devised a few ground rules for our selection process: We excluded faux pas that ultimately made the “victim” millions of dollars (Paris Hilton); nor were we interested in grossly off-putting transgressions (former Congressman Mark Foley).

Still, we’re going to bet that the people and companies we’ve picked would love a “do-over” for their mistakes. Well, maybe not all of them…

13. He’ll Huff and He’ll Huff and…

The Smoking Gun pretty much dedicates itself to showing people during their most humiliating moments, but the celebrity mugshots of James Brown, Nick Nolte, and Yasmine Bleeth have nothing on poor Patrick Tribett, who was nabbed for “abusing harmful intoxicants,” namely huffing gold spray paint.

Whether Tribett intentionally chose gold to match his “Warriors” t-shirt or whether the color just makes for a good high remains a mystery; but his overall look, which recalls a child who has ploughed headlong into a birthday cake, is mortifyingly priceless. The pose even earned Tribett his own YTMND Web page.

12. Putting as Much of America Online as Possible

When AOL posted the search records of 658,000 subscribers (ithe names were redacted and replaced with a unique number), the company couldn’t even fall back on the “It was an accident!” excuse. The release was intentional, part of a horribly misguided research project to give academics a data set to see what people were searching for online. Turns out folks were looking for the usual stuff: American Idol, Britney Spears, cheap plane tickets, and a whole lot of porn. AOL removed the data, but only after it had been well mirrored, searched, and reported on. The company’s apologies fell on deaf ears: AOL is currently being sued over the matter.

11. Meow!

A little Photoshop can be a dangerous thing. Cat Schwartz had some professional photographs made of herself and posted them on her blog. As they were obviously cropped into odd shapes, it didn’t take long before admirers started to wonder what had been cut out of the pics.

Unfortunately, Schwartz hadn’t accounted for Photoshop’s thumbnailing system, which creates its (quite sizable) thumbnails based on the original shot, not the crop. Turns out Schwartz was topless during the photo shoot, and had actually posted nude photos of herself online by accident. What makes this especially embarrassing is that Schwartz works as a technology reporter and commentator and, one would assume, should have known better. (No, we’re not going to link to it, and yes, you can find it without much trouble…but you wouldn’t do that, would you?)

Most Embarrassing Moments #10 to #8

10. OMG U R SO F1R3D!11!1! TTFN!

Laying off 2500 people means bringing in an army to provide loss counseling, job placement programs, a pile of severance checks, and a truckload of tissues to stem the tears, right? Not! In 2003 British Amulet Group “made redundant” thousands via an SMS text message sent en masse to employees’ cell phones. At least the company had a quasi-excuse: It had just gone bankrupt and was in receivership.

9. Just a ‘Conversation Malfunction’

Women are known to engage in a little private chitchat in the ladies’ room, but how would they feel if the conversation was broadcast on CNN during a presidential speech? When newsreader Kyra Phillips made a pit stop, she unfortunately left her microphone on, broadcasting the news that her sister-in-law was a “control freak,” among numerous other pronouncements. Phillips later laughed it off and even provided a Late Show Top Ten list of excuses for why it happened. Sample: “How was I supposed to know we had a reporter embedded in the bathroom?”

8. I’m Not Dead Yet!

It’s common practice for major media outlets to prepare obituaries in advance–known in the news biz as “pre-bits”–for luminaries who seem as if they might croak soon. But in 2001 some intrepid Web spelunkers discovered that CNN’s obituaries for some famous but not-quite-dead folks were publicly accessible. Obits for the likes of Fidel Castro, Dick Cheney, and Nelson Mandela were widely disseminated before CNN.com caught wind and, much chagrined, yanked the pages.

Most Embarrassing Moments #7 to #5

7. Two Words: Ketchup Trousers

Who says the British are eternally polite? After his secretary spilled a little ketchup on his pants, London lawyer Richard Phillips demanded restitution from her–via e-mail–in the amount of a measly £4. The subject line of that e-mail: “Ketchup Trousers.” The secretary failed to pay immediately, owing to her mother’s sudden death, but quickly made the David vs. Goliath matter public, humiliating Phillips. His firm later said that Phillips had resigned, but it was careful to note that the departure had nothing to do with the trousers incident. Which we totally believe.

6. The Case of the Wrong ‘Guy’

It was an honest mistake. The BBC, seeking to interview a technology expert in the “Apple Computer vs. the Beatles’ Apple Corps” dispute, booked Guy Kewney to appear on the air. But someone goofed and instead brought one Guy Goma to the set . His stunned look, when a reporter started asking him questions, is something you just can’t fake. Goma, originally reported to be a cab driver, actually turned out to be at the studio for a job interview. He later said he had thought the whole thing was some kind of initiation stunt. The BBC has since been vigilant about forcing online video sites to remove the embarrassing footage.

5. Well, It’s Not How PR Usually Works

A lot of companies make in-house motivational videos to rally the troops, but rarely do the films feature racial slurs and nudity. Kirk Reynolds, public relations director for the San Francisco 49ers, probably didn’t think his cheeky 15-minute primer on dealing with the press would actually be seen by the press, but of course it was quickly leaked. Reynolds was immediately fired, having forgotten the fundamental rule in his own tape: “Everything you say and do is being covered by the media.”

Most Embarrassing Moments #4 to #1

4. The Force Is With Him

In 2002 a 14-year-old Canadian boy named Ghyslain Raza innocently swung a golf-ball retriever around in a quiet corner of his high school, pretending he was The Phantom Menace’s Darth Maul. But he videotaped it. And he left the tape at school, where it was found several months later. Raza immediately became an Internet sensation, known today as the “Star Wars kid,” with fans adding light-saber effects and music, and creating video revisions that number over a hundred. The embarrassing footage has since become one of the Internet’s most popular memes, having been spoofed on TV shows ranging from American Dad to The Colbert Report to Arrested Development. In 2003 Raza sued those who posted the video online, but the case was settled earlier this year.

Honorable Mentions, Personal Embarrassment Category:

• Mahir “I Kiss You!” Cagri (The “real” Borat?)
• Randy “Peter Pan” Constan

3. I Scream, You Scream, We All Scream for Howard Dean

No one can be sure whether Howard Dean’s 2004 presidential campaign speech completely killed his chances of winning the Democratic nomination (he’d just finished third in the Iowa caucus), but the infamous “Dean Scream” has become a political cautionary lesson as infamous as Michael Dukakis’s “Snoopy” appearance in 1988.

Dean gave a passionate speech reeling off the states he would soon conquer, and then, overcompensating for crowd noise, punctuated the affair with a yell that was part rodeo call, part slasher movie sound effect, and part yodel. A sheepish Dean dropped out of the race days later after the episode received heavy TV airplay. It’s now a remix staple. (Don’t miss “Deansane in the Brain.”)

2. Guns Don’t Kill People, They Just Blow Off a Toe or Two

Never mind that in 2004 some misguided Florida children’s group invited Lee Paige, a 45-year-old Drug Enforcement Agency officer, into an auditorium with a loaded gun to demonstrate weapons handling. That’s bad enough, but the bigger embarrassment is actually Paige’s, which came just after he told the young kids, “I’m the only one in the room that I know of that’s professional enough to carry a Glock .40.”

Paige promptly shot himself in the foot, and then actually tried to continue his speech, hobbling around and asking for an assault rifle until a terrified room of kids begged him to stop. Caught on film, Paige was (rightly) ridiculed to the point where he has sued the government for “illegally” making the tape in the first place. Good luck with that.

1. That’s One Way to Rally the Troops

Steve Ballmer, CEO of Microsoft, will stop at nothing to keep the legions of Microsoft employees motivated and entertained, even at his own expense.

It must have been this spirit that prompted Ballmer to take the stage during a 2001 company event to the tune of Gloria Estefan’s “Get on Your Feet,” performing what was quickly dubbed “The Monkey Boy Dance.” Part “Skip to My Lou” and part Nazi goose step, Ballmer “danced” while screaming at his minions: “Wooooo! Get up! Come on! Give it up for me!” A few days later, an unrepentant and sweat-drenched Ballmer would lead a crowd to repeatedly chant “Developers!” Video remixes of both performances abound.