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 (the 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?)

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’ People are known to engage in a little private chitchat in the washroom, 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 caught wind and, much chagrined, yanked the pages.

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

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Jim Love, Chief Content Officer, IT World Canada

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