14. Lauryn Hill "Doo Wop (That Thing)" (1998)
Director: Big TV!
Album: The Miseducation of Lauryn Hill
"Don't be a hard rock when you really are a gem," was Lauryn's advice for women in her one and only No. 1 hit, "Doo Wop (That Thing)." The two-time Grammy winning track off The Miseducation of Lauryn Hill got split-screen visuals in the Big TV! produced video. Taking place in Washington Heights, Lauryn performed at two block parties from two generations—1967 and 1998, which displayed the vast differences between men and women during the 30-year gap. —Lauren Nostro