The 13 Most Embarrassing Web Moments

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."