44. R. Kelly "I Believe I Can Fly" (1996)

Director: Hype Williams
Album: Space Jam: Music From and Inspired by the Motion Picture

Before the cornrows, there was the cornfield. R. Kelly's video for his inspirational Space Jam single keeps it simple, but all it takes is a few striking images to burn into your memory forever. The strongest of them all? Kellz leading an orchestra, complete with conductor wand and hands-free headset. His career, or look, hasn't been the same since. -Ernest Baker