22. Enrique Iglesias, "Escape"
2001's fizzy yet determined "Escape" was accompanied by a clip that allowed Iglesias and his then-girlfriend, Russian tennis player Anna Kournikova, to let viewers in on how tough dating while famous can be. Stolen moments in a ladies' room and a parking lot are steamy, but cut short by eagle-eyed security guards – until Iglesias' concert ends and Kournikova sticks around for a long-awaited kiss. "It was my first video and it was pretty sexy," Kournikova told the British Mirror, "but that's not difficult when you're acting with Enrique."