44. Ol' Dirty Bastard f/ Kelis "Got Your Money" (1999)
Director: Nzingha Stewart, Scott Kalvert, Hype Williams, D'Urville Martin
Can you imagine trying to manage ODB during a video shoot? The always idiosyncratic rapper is missing from most of this video, which is mostly footage from the blaxplotation film Dolomite with ODB's face planted over characters here and there. It was so absurd and unexpected, that it came off as fairly brilliant.