MTV Video Music Awards | 1999

MTV Video Music Awards

1999 Video Music Awards

Host: Chris Rock
Venue: Metropolitan Opera House
City: New York City, NY
Date: September 9, 1999

Video of the Year: Lauryn Hill "Doo Wop (That Thing)"

1999 Video Music Awards

Ping-pong being one of the favorite pastimes at MTV, we switched coasts again in 1999, bringing the Video Music Awards back into New York after a lengthy one year stint in Los Angeles. But we were in the mood to break the mold a bit, so no more Radio City Music Hall for us. We went uptown, staging the VMAs at an even more respected venue, the Metropolitan Opera House. Oh yeah, it was time to desecrate the arts!

No, no, no. Not really. But it was odd to put a show that's known for its insane and outrageous pop culture moments into a place where the idea of culture is something that is ageless and far more refined. Knowing that we were in rarified air, we decided to bring back Chris Rock as host, cuz he's sensitive, right?

Diana Ross and Lil' KimSo, sensitive he's not. But he's sure as hell funny. But anything Chris did or said was upstaged by a diminutive female rapper named Lil' Kim. We got our first glimpse of Kim and her outfit during a pre-show interview. When the show started, our collective jaw was still on the floor at having seen, well, her entire boob, save for the bit covered by a pasty that matched her outfit!

But maybe it wasn't Lil' Kim who stole the show at the 1999 MTV Video Music Awards. See, we weren't the only ones fixated on that breast. None other than R&B royalty Diana Ross couldn't get enough of that thing, either, and when she took the stage with Kim and Mary J. Blige to present the Best Hip-Hop Video, she couldn't resist reaching over for a feel. Did you catch that? No? Let us sum it up: DIANA ROSS COPPED A FEEL OFF OF LIL' KIM ON TELEVISION. Second base, right before our very eyes. We admit it, we were jealous.

Well, it was the first time in VMA history that MTV presented a hip-hop award, and it went to the Beastie Boys for "Intergalactic." It was a solo Lauryn Hill who won big, taking three Moonmen for "Doo Wop (That Thing)," including Video of the Year. She didn't need no Fugees, now did she? Nope.

For the second year in a row, the Backstreet Boys took the Viewer's Choice Award for "I Want It That Way," a song they performed during the broadcast. *NSYNC also performed in a pairing with Britney Spears (remember the innocent days of Britney and Justin?) for her "Baby One More Time" and their "Tearin' Up My Heart."

Indeed, the boy band age was at its peak and going out on top. On its way in was a long-overdue Latin explosion. For that, Ricky Martin was honored with the Best Dance Video award for "Livin' La Vida Loca," a song and video that was so ubiquitous that your mom knew all of the words.

The 1999 VMAs were a coming out party for Marshall Mathers (the kids on the street call him Eminem), who won the Best New Artist award for "My Name Is." Because there's no street cred in performing on the VMAs, Slim Shady made up for it by bringing the street on stage, performing "My Name Is/Guilty Conscience/Nuthin' But a 'G' Thang" with Dr. Dre and Snoop Dogg.

The show also featured Run DMC with Aerosmith's Steven Tyler and Joe Perry and Kid Rock opening the proceedings with a medley of "King of Rock," "Rock Box," "Bawitdaba" and "Walk This Way." Rock's diminutive side-kick/hype man Joe C also joined in the fun, making him the biggest little ladies man at the show.

With Nine Inch Nails, TLC and Jay-Z also on the bill, the 1999 show was a performance monster, breaking down genre walls and more or less blowing the roof off of the staid surroundings at the Met.

And the night featured honors of a bigger nature. First, Madonna -- the most nominated artist in VMA history -- was fetted with a tribute in the form of men in drag dressed in outfits from every one of her music videos. And while that was touching, it couldn't hold a candle to Afeni Shakur and Voletta Wallace, the mothers of slain rappers Tupac and Notorious B.I.G., appeared onstage together to present the Best Rap Video award.

See, we're good for some honorable things, too.