The 13 Most Embarrassing Web Moments

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Most Embarrassing Moments #4 to #1

4. The Force Is With Him

Star Wars kid
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:

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

The "Dean Scream"
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

Microsoft head cheeleader Steve Ballmer
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.

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