Year: 2009
1960s Mercedes-Benz

A video that later goes on to boast appearances from the likes of Harvey Keitel and LeBron starts off with one of the best music video cameos ever when Jay pulls up in an early model Benz chauffeured by none other than Lyor freaking Cohen. This is one of those simple, stand around and rap videos but is there really a need to do more when one of the most powerful men in hip-hop agrees to play chauffeur for a scene?