1999 MTV Video Music Awards


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 four 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 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.
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.

Nominations

Winners are in bold text.

Video of the Year

Lauryn Hill – "Doo Wop "
Will Smith – "Miami"
Lauryn Hill – "Doo Wop "
TLC – "No Scrubs"
Eminem – "My Name Is"
Ricky Martin – "Livin' la Vida Loca"
Korn – "Freak on a Leash"
Lauryn Hill – "Doo Wop "
Jay-Z – "Can I Get A..."
Beastie Boys – "Intergalactic"
Ricky Martin – "Livin' la Vida Loca"
Madonna – "Beautiful Stranger"
Fatboy Slim – "Praise You"
Fatboy Slim – "Praise You"
Fatboy Slim – "Praise You"
Garbage – "Special"
Lauryn Hill – "Doo Wop "
Korn – "Freak on a Leash"
Marilyn Manson – "The Dope Show"
Red Hot Chili Peppers
Backstreet Boys – "I Want It That Way"

[MTV Australia]

Silverchair – "Anthem for the Year 2000"
Raimundos – "Mulher de Fases"
A. R. Rahman – "Dil Se Re"
H.O.T. – "Make a Line"
Ricky Martin – "Livin' la Vida Loca"
Ricky Martin – "Livin' la Vida Loca"
Shino Lin – "Irritated"
Ricky Martin – "Livin' la Vida Loca"
Parokya ni Edgar – "Harana"

Pre-show

Pre-show