5 Best Hip Hop Moments From The 1999 MTV Video Music Awards

On September 9, 1999, the sixteenth annual MTV Video Music Awards took place at the Metropolitan Opera House in New York City, and instantly claimed the title as one of the most memorable, controversial and iconic moments in music history — Hip Hop specifically. With the end of the millennium looming, the impeachment trial of President Bill Clinton coming to an end and tensions rising in the Black community with law enforcement; most of the world was exhausted, on edge and in need of some entertainment.  

Hip Hop was in it's golden age at the time, turning artists like DMX, Lauryn Hill and Eminem into global superstars. The 1999 VMAs, hosted by Chris Rock, gave the culture a plethora of legendary moments to feed on forever. Here are five of the greatest Hip Hop moments from the 1999 MTV Video Music Awards.

The mothers of late rappers Tupac Shakur and The Notorious B.I.G., Afeni Shakur and Voletta Wallace, came together to present the Best Rap Video Award along with Will Smith.

Lil Kim donned the infamous purple pasties outfit, and Diana Ross (more infamously) playfully grabbed her breast.

Lauryn Hill’s “Doo Wop (That Thing)” becomes the first Hip Hop video to the award for Video Of The Year, beating out Ricky Martin who became the first Latin Artist to receive a nomination in the category. Hill went on to win four awards that night.

DMX was scheduled to perform but didn’t show up. As a result, Jay-Z's solo set was extended, bringing what was then deemed “hardcore hip hop” to the MTV audience.

Eminem performed on the big stage for the first time and took home the award for Best New Artist.