16. Jay-Z "Girls, Girls, Girls" (2001)

Director: Marc Klasfeld
Album: The Blueprint

Every girl Jay-Z mentions in the song is depicted so accurately in this video. Carmen Elektra plays the girl who thinks she's Bo Derrick, the narcoleptic girl has her head propped with a rope because she's always "sleepin' on Hov," they're all on point. Plus Biz Markie has a special guest appearance to help out with the hook. Just as an aside, this was long before Beyonce.