35. Usher "My Way" (1998)

Director: Hype Williams
Album: My Way

"My Way" already hit high on the Billboard charts with its sexual, alpha male ambitions, so Usher had some leeway in this clip. The result: bowler hats, hockey sticks, intensely colorful blazers, and a dance-off. Think of an urbanized Clockwork Orange-style clip, with more Tyrese. -Brian Josephs