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. "
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."
More embarassing moments at PC World.com