Album: Unleash the Dragon

At the height of his career, one that included two platinum-selling records with the group Dru Hill, Sisqo decided the time was ripe to strike out on his own and try his hand at solo stardom. His first single, "Got to Get It," failed to drum up much attention. However, the next single would make the silver-haired singer a household name.

Ostensibly an ode to underwear, "Thong Song" would catapult Sisqo into superstardom despite being one of the silliest songs ever recorded. Have you read the lyrics? Let's forget the parts where he pleads to see a girl's thong. Let's instead focus on where he says the girl "cruise to the crew like connect the dots." What? What does that mean? And why is he singing it like his next bottle of hair dye depended on it? It's not surprising that Sisqo's solo career would careen down a cliff afterwards.—Damien Scott