37. Redman "I'll Bee Dat" (1998)

Director: Director X

This video is a classic off one scene. You know what we're talking about. Hot girl rides her bike, waves at the homies, the homies wave back, and--BOOM--she runs into a parked car and totals her bike and face. Not a good look for the cyclist, but an unforgettable and hilarious moment in rap video history. Beyond that, Redman dancing with big girls, stealing a BMW, and pumping his own brands of cereal and cola all contribute to the sheer awesomeness of this clip.