The 1999 MTV Video Music Awards aired live on September 9, 1999, honoring the best music videos from June 13, 1998, to June 11, 1999. The show was hosted by Chris Rock at Metropolitan Opera House in New York City. Lauryn Hill was the big winner of the night, taking home 4 Moonmen, including Best Female Video and the big one, Video of the Year
Highlights of the show included Diana Ross jiggling Lil' Kim's exposed breast in response to her outfit, which left her entire left breast uncovered, but for a small pastie on her nipple. The mothers of slain rappers Tupac Shakur and The Notorious B.I.G., Afeni Shakur and Voletta Wallace, came together to present the Best Rap Video Award. The Beastie Boys' Adam Horovitz made a plea for peace in the wake of the sexual assaults at Woodstock '99. Near the end of the night, MTV staged a tribute to Madonna, the most-nominated artist in VMA history, by presenting a host of male drag performers dressed as the singer her past music videos. Rapper DMX was scheduled to perform but was a no-show; as a result, Jay-Z's solo set was extended.
The show is most remembered for when Backstreet Boys came up and accepted their award for Viewer's Choice, a stranger came onto the stage and said, "Wake up at 3". The stranger's identity is unknown.
Read more about 1999 MTV Video Music Awards: Aborted Performance, Appearances
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