The 1999 VMAs Were A Culmination Of Hip Hop’s Transcendence

Written by: Zachary Draves


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Twenty-five years ago, the MTV Video Music Awards celebrated the diversity of hip hop during an impactful year. 

By the dawn of the new millennium, hip-hop was at a crossroads. 

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There was still a significant void after the killings of Tupac Shakur in 1996 and the Notorious B.I.G. in 1997. Their deaths stemmed from an intense east coast/west coast turf war where nobody dared to cross enemy lines. 

Allegiances were seemingly set in stone, but cracks started to show in 1999. There was plenty of talent to go around regardless of the fealty of one particular region.

Jay Z, Nas, and DMX respectively took over New York. Eminem put Detroit on the map with the release of The Slim Shady LP. Snoop Dogg found peace with Master P’s No Limit Records after tumultuous tenure with Death Row Records and the release of his No Limit debut No Limit Top Dogg. Cash Money Records featuring Lil Wayne, B.G, the Hot Boys, and Juvenile helped to sustain the south. 

The phenomena of nu-metal, a unique blend of rap, heavy metal, and grunge, were pervasive with Limp Bizkit and Korn.

Women in hip hop reached critical mass in 1999. Lauryn Hill was riding high off the success of her groundbreaking album The Miseducation of Lauryn Hill. Lil Kim was coming into her own post Biggie with her blistering lyricism and fashion sense as she prepped for her second album The Notorious K.I.M. Missy Elliot held double duty as a trendsetting artist, producer, and music video revolutionary with her sophomore album Da Real World. TLC came back from a five year hiatus with their fan appreciation album Fanmail

The moral panic surrounding the perceived social ills of popular music and its connection with youth culture had shifted towards the satanism of Marilyn Manson and so called “goth music”. In the aftermath of that year’s shooting at Columbine High School in Littleton, Colorado the shooters were accused of being influenced by the music.

A few years prior it was “gangsta rap” being subjected to congressional hearings and organized boycotts of  Time Warner and other major labels by civic leaders such as C. Delores Tucker alongside former Reagan Education Secretary William Bennett. 

By 1999, hip hop was an embedded part of American popular culture. It was infused into everything from movies, commercials, sports, and fashion. 

Those elements came to the fore at the Metropolitan Opera House in New York City during some notable moments. 

Lauryn Hill took home four awards, including the VMA for the coveted Video Of The Year for “Doo Wop (That Thing).” 

Lil Kim rocked a lavender pasties outfit inspired by Missy Elliot, and Diana Ross jiggled her breast while presenting the award for Best Hip Hop Video alongside Mary J. Blige, where The Beastie Boys won for their song ”Intergalactic”

It was during the acceptance speech that Adam Horovitz made a plea about respect for women and girls and safety at music festivals after the horrific acts of violence on display at that summer’s Woodstock 99, where there were multiple incidents of sexual assault. 

In a heartfelt moment, Will Smith introduced Afeni Shakur (Tupac mother’s) and Voletta Wallace (Biggie’s mother) to present the award for Best Rap Video, which went to Jay Z for “Can I Get A…” ft. Ja Rule and Amil off the Rush Hour soundtrack. 

Eminem won for Best New Artist Video for “My Name Is” while also performing alongside Snoop Dogg and Dr Dre. TLC performed “No Scrubs,” and the video won for Best Group Video. 

In replacement of DMX, who was scheduled to perform, Jay Z took the stage and performed “It’s A Hard Knock Life”, “Can I Get A…”, and “Jigga My N—-”.

The 99 VMAs were more than an annual award ceremony honoring the best in music at the dawn of a new century; they solidified hip hop’s forever place in the broader culture. 

There wasn’t a need for any singular voice or even a handful to carry the weight, a collection of artists with a vast array of skills from all regions of the country kept the music alive.