Which VMA Video Of The Year Winner From The Last 20 Years Is The Most Timeless?

by (@unclegrambo)

11. VIDEO: Lauryn Hill, “Doo Wop (That Thing)”
YEAR: 1999

Speaking of people who were poised to be the Next Big Thing but promptly fell off the map, Lauryn Hill’s legacy is one of the saddest of all. Currently serving time in state prison on tax evasion charges, the world was Hill’s oyster when she dropped The Miseducation of Lauryn Hill on the heels of the worldwide fame she garnered as a member of The Fugees. “Doo Wop” is a timeless track, and an equally timeless video that was a direct influence on future Video Of The Year award winners like Outkast’s “Hey Ya.”

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