The 1999 MTV Video Music Awards (stylized as 9999 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 the Metropolitan Opera House in New York City.[1] Ricky Martin was the most-awarded artist of the night, winning two primary awards for Best Pop Video and Best Dance Video, and three additional awards in the International Viewer's Choice categories for "Livin' la Vida Loca".[2] Martin and Korn were the most nominated artists of the night, both with 9 nominations for their songs, "Livin' la Vida Loca" and "Freak on a Leash", respectively. Martin was also the first Latin artist in history to receive a nomination in Video of the Year category,[3] but lost to "Doo Wop (That Thing)" by Lauryn Hill, which became the first Hip hop video to receive the award.[4][5]
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 in 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. Another moment of the ceremony was the debut of Britney Spears performing her debut single "...Baby One More Time", and then, NSYNC, performed their song "Tearin' Up My Heart".
As Backstreet Boys came up and accepted their award for Viewer's Choice, a stranger came onto the stage and said, "Wake up at 3". This person was later revealed to be John Del Signore, who crashed the ceremony in a failed attempt to sell Viacom a show idea.[6]
The awards show featured a line-up of sponsors and cross-promotions, most notably with SEGA, as the date of the show also coincided with the launch of their Dreamcast game console.
^Queen, Alexis (December 25, 2023). "Why the 1999 MTV Video Music Awards Were the Death of the '90s". Throwback Pop. Archived from the original on February 1, 2024. Retrieved March 9, 2024.
^Kaufmang, Gil (September 10, 1999). "Ricky Martin, Lauryn Hill Dominate at MTV Video Music Awards". MTV News. Archived from the original on June 26, 2020. Retrieved May 24, 2021.
^Unterberger, Andrew (July 21, 2020). "Who'll Be Nominated For Video of the Year at the 2020 VMAs? Sizing Up the Most Likely Contenders". Billboard. Archived from the original on May 24, 2021. Retrieved May 24, 2021.
^Weingarten, Christopher R. (August 25, 2018). "Flashback: See Lauryn Hill Perform Lush Version of 'Lost Ones' at MTV VMAs". Rolling Stone. Archived from the original on August 26, 2018. Retrieved March 21, 2021.
^Anthony, Kiyonna (September 10, 2021). "5 Best Hip Hop Moments From The 1999 MTV Video Music Awards". iHeartRadio. Archived from the original on September 11, 2021. Retrieved September 11, 2021.
^Del Signore, John (November 6, 2009). "Bite Me, Kanye! I Bum-Rushed the MTV Video Music Awards, Ten Years Ago This Week". The Awl. Archived from the original on March 28, 2013. Retrieved August 25, 2013.
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