The MTV VMAs were back in New York in 1999, but on a different stage this time around. MTV had brought back Funnyman Chris rock to host the show. Only this time it was a different venue in New York, the historical Metropolitan Opera House. Chris’s opening lines (“I may be the first black man in history to be on the stage of the Met without a mop”) gave the audience a feel of the history behind the Metropolitan Opera house. While Chris took a breather, a certain female rapper by the name of Lil’ Kim took to the stage with Diana Ross and Mary J Blige and got a collective gasp from the crowd that even Chris hadn’t managed. Lauryn Hill didn’t look so lost without the Fugees, she walked away with four Moonmen for her Doo Wop (That Thing). Fatboy Slim went home with three awards including the one for Breakthrough Video. Best Hip-Hop Video went to Beastie Boys and Eminem was awarded Best New Artist for his worldwide hit My Name Is. Eminem later performed on stage with Dr. Dre and Snoop Dogg.
Also on the bill at the awards were winners Lauryn Hill, Backstreet Boys and Ricky Martin. NSync and Britney Spears collaborated on Baby One More Time / Tearin' Up My Heart. The Show also witnessed a tribute to Madonna and a surprise visit from the mothers of slain artists Tupac Shakur and Notorious B.I.G. who came up with Will Smith to present the award for Best Rap Video. The show had it all, shockers, tributes, humor, unforgettable performances, et al.
List of Nominees and Winners at the MTV Video Music Awards 1999
Video of the Year
- Lauryn Hill - Doo Wop (That Thing)
- Backstreet Boys - I Want It That Way
- KoRn - Freak On A Leash
- Ricky Martin - Livin' La Vida Loca
- Will Smith f/ Dru Hill & Kool Moe Dee - Wild Wild West
Best Male Video
- Will Smith - Miami
- Eminem - My Name Is
- Lenny Kravitz - Fly Away
- Ricky Martin - Livin' La Vida Loca
Best Female Video
- Lauryn Hill - Doo Wop (That Thing)
- Jennifer Lopez - If You Had My Love
- Madonna - Get Ur Freak On
- Britney Spears - Baby One More Time
Best Group Video
- TLC - No Scrubs
- Backstreet Boys - I Want It That Way
- Limp Bizkit - Nookie
- NSYNC - Tearin' Up My Heart
- Sugar Ray - Every Morning
Best Pop Video
- Ricky Martin - Livin' La Vida Loca
- Backstreet Boys - I Want It That Way
- Jennifer Lopez - If You Had My Love
- NSYNC - Tearin' Up My Heart
- Britney Spears - Baby One More Time
Best Rap Video
- Jay-Z f/ Ja Rule & Amil - Can I Get A...
- 2Pac - Changes
- DMX - Ruff Ryder's Anthem (Stop Drop)
- Nas f/ Puff Daddy - Hate Me Now
Best R&B Video
- Lauryn Hill - Doo Wop (That Thing)
- Aaliyah - Are You That Somebody?
- Brandy - Have You Ever?
- Whitney Houston f/ Faith Evans & Kelly Price - Heartbreak Hotel
Best Hip-Hop Video
- Beastie Boys
- Busta Rhymes f/ Janet Jackson - What's It Gonna Be
- Lauryn Hill - Doo Wop (That Thing)
- TLC - No Scrubs
Best Dance Video
- Ricky Martin - Livin' La Vida Loca
- Cher - Believe
- Fatboy Slim - Praise You
- Jordan Knight - Give It To You
- Jennifer Lopez - If You Had My Love
Best Rock Video
- KoRn - Freak On A Leash
- Limp Bizkit - Nookie
- Kid Rock - Bawitdaba
- Lenny Kravitz - Fly Away
- The Offspring - Pretty Fly (For A White Guy)
Viewer's Choice
- Backstreet Boys - I Want It That Way
- NSYNC - Tearin' Up My Heart
- Jay-Z f/ Ja Rule & Amil - Can I Get A...
- KoRn - Freak On A Leash
- Ricky Martin - Livin' La Vida Loca
- TLC - No Scrubs
Best New Artist
- Eminem - My Name Is
- Kid Rock - Bawitdaba
- Jennifer Lopez - If You Had My Love
- Orgy - Blue Monday
Breakthrough Video
- Fatboy Slim - Praise You
- Busta Rhymes - Gimme Some More
- Eels - Last Stop: This Town
- Eminem f/ Dr. Dre - Guilty Conscience
- KoRn - Freak On A Leash
- U.N.K.L.E. - Rabbit In Your Headlight
Best Video From A Film
- Madonna - Beautiful Stranger
- Aaliyah - Are You That Somebody?
- Jay-Z f/ Ja Rule & Amil - Can I Get A...
- Will Smith f/ Dru Hill & Kool Moe Dee - Wild Wild West
Best Direction
- Fatboy Slim - Praise You
- Busta Rhymes f/ Janet Jackson - What's It Gonna Be
- Eminem - My Name Is
- KoRn - Freak On A Leash
- TLC - No Scrubs
Best Choreography
- Fatboy Slim - Praise You
- Ricky Martin - Livin' La Vida Loca
- Will Smith f/ Dru Hill & Kool Moe Dee - Wild Wild West
- Britney Spears - Baby One More Time
Best Special Effects
- Garbage
- Black Eyed Peas - Joints & Jams
- Busta Rhymes f/ Janet Jackson - What's It Gonna Be
- KoRn - Freak on a Leash
- Madonna - Nothing Really Matters
- Will Smith – Miami
Best Art Direction
- Lauryn Hill - Doo Wop (That Thing)
- Barenaked Ladies - One Week
- Busta Rhymes f/ Janet Jackson - What's It Gonna Be
- KoRn - Freak On A Leash
- TLC - No Scrubs
Best Editing
- KoRn - Freak On A Leash
- 2Pac - Changes
- Cher - Believe
- TLC - No Scrubs
Best Cinematography
- Marilyn Manson -The Dope Show
- Hole - Malibu
- KoRn - Freak On A Leash
- Madonna - Beautiful Stranger
- Will Smith – Miami
Winner: Marilyn Manson -The Dope Show