41. Donell Jones f/ Left Eye "U Know What's Up" (1999)

Director: David Nelson
Album: Where I Wanna Be

Donnell Jones' 1999 hit "U Know What's Up" would become his biggest, topping the R&B charts and reaching No. 7 on the Billboard Hot 100. The video is a strange meta-commentary on watching music videos, as it follows air ducts in a variety of apartments where some alternate version of Donnell Jones' video is playing on the TVs in each apartment. After a quick CGI-enhanced A/C airshaft voyage, we're transported to a room where a DJ is practicing his scratches, or where a girl is braiding her boyfriend's hair, or where one woman pole dances for a seated audience.

After guest rapper Left Eye strides through the halls dressed in angelic white, we arrive at a party in-progress, before the video ends with Donnell and his girl sitting together watching himself on TV. The video may have been a little off the familiar path, but it helped set the stage for the song's success. Where I Wanna Be, the album from which it was culled, went on to ship platinum, Jones' highest-selling record. -David Drake