Year: 2002
Director: Chris Robinson

Diddy and his entourage move into the white suburbs, and hilarity ensues. The cameos are unmatched—this man has some serious friends. Dave Navarro?

YOU AUGHTA KNOW:
Director Chris Robinson also made Alicia Keys' "Fallin'" and "You Don't Know My Name", "Roc Boys" by Jay Z, "One Mic" by Nas, and "Bonnie & Clyde '03" by Hov and B.