Who won Video of the Year in 1999 for “Doo Wop (That Thing)”?

Lauryn Hill won Video of the Year at the 1999 MTV Video Music Awards for “Doo Wop (That Thing)”.

The video presented Hill in a split-screen concept: one side evoked 1960s doo-wop and soul, while the other reflected contemporary hip-hop culture. Directed by Monty Whitebloom and Andy Delaney, it visually reinforced the song’s dialogue between musical eras and social perspectives.

Hill was the night’s biggest winner, taking four awards. Her Video of the Year victory was historically significant because “Doo Wop (That Thing)” became the first hip-hop video to win the category. It also made Hill the first solo Black artist to receive that top VMA honor.

A common mix-up is to credit the Fugees, Hill’s former group, rather than Hill herself. The 1999 award recognized Lauryn Hill as the solo artist behind the video, following the release of her landmark album The Miseducation of Lauryn Hill.