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?)