3. PARIS HILTON

Music Video: "Just Lose It" (2004)
At the height of Paris Hilton's fame as a socialite turned one-time porn star, she appropriately made a cameo in one of Eminem's silliest celeb-roasting videos (the targets this time: Michael Jackson and Madonna, among others). Hilton plays a club girl who punches Em in the stomach to satisfy his apparently sadomasichistic request. We speculate that casting directors thought she was perfect for the slightly S&M role after they accidentally sat through an episode of The Simple Life.