19. Jay-Z "Hard Knock Life (Ghetto Anthem)" (1998)
Director: Steve Carr
The video for "Hard Knock Life" isn't particularly complicated or flamboyant, as no video about growing up in poverty should be, but it's not a trite account of "the struggle" either. If anything, the video that made Jay-Z a superstar was refreshingly honest-a low-frills joyride in an era exploding with over-the-top visuals. It's the video that added a welcome new dimension "hanging out in my old hood" clips, and made putting little kids in rap videos a thing for a couple years after. From the moment Hov cracks open that quarter water in the bodega to final shot of children perched on his blue Bentley, it gets an even more classic sheen on each viewing.