21. OutKast "Hey Ya!" (2003)
Director: Bryan Barber
Album: Speakerboxxx/The Love Below
By the time Andre 3000 reached the "Hey Ya" era of his career, not a single fuck was a given over whether or not he was acting "Hip-Hop" enough. In this 60s-inspired video Dre's hair is pressed and straightened, and the video shows 3-Stacks in his own rock band, where each member is inadvertently a version of himself throughout his career. It's a total reflection of how much Andre Benjamin has reinvented himself throughout the tenure of Outkast. Imagine how many more personalities could be added to this video now?