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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.[1] 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

1999 MTV Video Music Awards
DateThursday, September 9, 1999
LocationMetropolitan Opera House, New York City
CountryUnited States
Hosted byChris Rock
Television/radio coverage

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.[2]

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.



Winners are in bold text.

Video of the YearEdit

Lauryn Hill – "Doo Wop (That Thing)"

Best Male VideoEdit

Will Smith – "Miami"

Best Female VideoEdit

Lauryn Hill – "Doo Wop (That Thing)"

Best Group VideoEdit

TLC – "No Scrubs"

Best New Artist in a VideoEdit

Eminem – "My Name Is"

Best Pop VideoEdit

Ricky Martin – "Livin' la Vida Loca"

Best Rock VideoEdit

Korn – "Freak on a Leash"

Best R&B VideoEdit

Lauryn Hill – "Doo Wop (That Thing)"

Best Rap VideoEdit

Jay-Z (featuring Ja Rule and Amil) – "Can I Get A..."

Best Hip-Hop VideoEdit

Beastie Boys – "Intergalactic"

Best Dance VideoEdit

Ricky Martin – "Livin' la Vida Loca"

Best Video from a FilmEdit

Madonna – "Beautiful Stranger" (from Austin Powers: The Spy Who Shagged Me)

Breakthrough VideoEdit

Fatboy Slim – "Praise You"

Best Direction in a VideoEdit

Fatboy Slim – "Praise You" (Director: Torrance Community Dance Group)

Best Choreography in a VideoEdit

Fatboy Slim – "Praise You" (Choreographers: Richard Koufey and Michael Rooney)

Best Special Effects in a VideoEdit

Garbage – "Special" (Special Effects: Sean Broughton, Stuart D. Gordon and Paul Simpson of Digital Domain)

Best Art Direction in a VideoEdit

Lauryn Hill – "Doo Wop (That Thing)" (Art Director: Gideon Ponte)

Best Editing in a VideoEdit

Korn – "Freak on a Leash" (Editors: Haines Hall and Michael Sachs)

Best Cinematography in a VideoEdit

Marilyn Manson – "The Dope Show" (Director of Photography: Martin Coppen)

Best Artist WebsiteEdit

Red Hot Chili Peppers (

Viewer's ChoiceEdit

Backstreet Boys – "I Want It That Way"

International Viewer's Choice AwardsEdit

MTV AustraliaEdit

Silverchair – "Anthem for the Year 2000"

MTV BrasilEdit

Raimundos – "Mulher de Fases"

MTV IndiaEdit

A. R. Rahman – "Dil Se Re"

MTV KoreaEdit

H.O.T. – "Make a Line"

MTV Latin America (North)Edit

Ricky Martin – "Livin' la Vida Loca"

MTV Latin America (South)Edit

Ricky Martin – "Livin' la Vida Loca"

MTV MandarinEdit

Shino Lin – "Irritated"

MTV RussiaEdit

Ricky Martin – "Livin' la Vida Loca"

MTV Southeast AsiaEdit

Parokya ni Edgar – "Harana"



See alsoEdit

External linksEdit


  1. ^ "Lauryn Hill, Ricky Martin and Fatboy Slim Dominate TheFinal MTV Video Music Awards Of The 20th Century". Business Wire. 10 September 1999. Retrieved 2011-05-20.
  2. ^ "Archived copy". Archived from the original on 2013-03-28. Retrieved 2013-08-25.CS1 maint: Archived copy as title (link)
  3. ^ "Kids ThinkLink - CultureLink". Archived from the original on 2009-07-22. Retrieved 2009-06-30.