The 1990s were a transformative and influential decade. And the 1999 MTV Video Music Awards marked a turning point that signaled the end of an era.
This iconic event — held at the Metropolitan Opera House in New York City — encapsulated the changing cultural landscape at the time. It also foreshadowed the shifts that would define the new millennium.
From the performances to the fashion choices, the 1999 VMAs were not just a celebration, but the beginning of the end of the greatest decade ever.
Remembering the 1999 MTV Video Music Awards
The 1999 VMAs were hosted by comedian Chris Rock. And while his “shock comedy” shtick was super 90s (and doesn’t age too well), the real highlight of the show was the music. After all, it’s what we all remember most about that generation of MTV.
Under the bright lights, Britney Spears performed “…Baby One More Time” in a provocative schoolgirl outfit. Eminem rocked the crowd with his first big hit, “My Name Is.” Heck, it doesn’t get any more 1999 than “All Star” by Smash Mouth — the very first live performance on the pre-show.
While acts like Britney Spears and the Backstreet Boys represented the mainstream pop explosion, there was also a presence of alternative rock bands like Korn and the Red Hot Chili Peppers. Jay Z and Fatboy Slim were huge stars at the time, too.
This diverse array of musical styles was a huge influence on anyone who grew up watching MTV regularly in the late 90s.
The Y2K Fashion Trends Were Everywhere
The fashion choices at the 1999 VMAs mirrored the evolving aesthetic of the late ’90s.
Artists like Lil’ Kim and Christina Aguilera pushed boundaries with bold and risqué outfits. These futuristic outfits challenge the more subdued fashion of the earlier ’90s. Flamboyance and experimentalism were in and grunge and minimalism were out.
A New Face of Fame
The rise of reality TV and celebrity culture was another element of the 1999 VMAs that marked the end of the ’90s. The event saw the presence of reality TV stars. This indicated a shift towards a new form of celebrity culture that would become increasingly dominant in the 2000s.
The line between fame and infamy began to blur. This set the stage for the celebrity-obsessed culture that would define the following decade.
The 1999 MTV VMAs 25 Years Later
In retrospect, the 1999 MTV Video Music Awards can be seen as the death knell of the 1990s. The event encapsulated the changing musical landscape. It highlighted the evolving fashion trends. And it showcased the emergence of a new celebrity culture.
While the ’90s left an indelible mark on popular culture, the 1999 VMAs marked the end of an era, paving the way for the dynamic and unpredictable landscape of the 2000s.