12. Jay-Z f/ UGK "Big Pimpin'" (2000)

Director: Hype Williams
Album: Vol. 3... Life and Times of S. Carter

"Big Pimpin'" wasn't just a song; it was a lifestyle. And nothing communicated that lifestyle quite like its big-budget, Hype WIlliams-directed video, filmed on a tropical yacht. Shot in Trinidad during the Carnival street parade, the video was a lavish spectacle of conspicuous hedonism. The definition of "pimping" became something you could buy into, a strange mutation from the world's second-oldest occupation to a wider escapist fantasy about power and absent consequence.