3 Unforgettable Moments from the 1999 MTV Video Music Awards

When the calendar flipped from 1999 to 2000, it didn’t just mark the end of a millennium. It was also the end of MTV’s cultural dominance.

According to Billboard, the 1999 Video Music Awards “represented peak MTV at the height of the Total Request Live era.” Music videos didn’t end, of course, but an audience tuning in collectively to watch the top videos of the day eventually gave way to entertainment on demand.

YouTube launched in 2005 and began pulling viewers from cable television. Also, by the mid-2000s, reality shows like Laguna Beach and its spinoff The Hills had pivoted MTV’s focus away from music television.

Though MTV continues to host an awards ceremony for music, the 1999 broadcast may have been the end of MTV’s classic era. Below are three unforgettable moments from when the VMAs peaked 25 years ago.

Britney Spears and NSYNC Made Their VMA Debuts

Britney Spears performed her first single “Baby One More Time,” which kick-started a new era for pop music. Her high school stage performance was followed by NSYNC singing and dancing through “Tearin’ Up My Heart.” This was a time when Justin Timberlake was just one part of a boy band. Both Spears and Timberlake became cultural obsessions whose personal lives consumed the tabloids. Their 1999 performances at the VMAs seemed innocent compared to what followed. Especially for Spears.

Eminem Wins Best New Artist

Eminem has received 15 Video Music Awards, more than any male artist. It began in 1999 when he won Best New Artist. Metallica’s Lars Ulrich introduced the Detroit rapper before performances of “My Name Is” and “Guilty Conscience” with Dr. Dre. His alter ego, Slim Shady, became a 2000s touchstone and lifted Eminem from the underground. In the following decade, he became the best-selling artist in the United States.

The Mothers of Tupac Shakur and The Notorious B.I.G. Present Best Rap Video

Perhaps the most memorable moment and certainly the most moving happened when Afeni Shakur and Voletta Wallace hugged onstage before presenting the award for Best Rap Video. Shakur and Wallace each lost sons to gun violence.

Ms. Shakur said, “In keeping with both our sons’ memories and contributions to the arts, we stand united as mothers preserving their legacies.” Then Ms. Wallace added, “The fact that we are even standing here shows what the power of faith, friends, family, loved ones, and fans can do to bring us all closer.”

Will Smith—the category’s first winner in 1989—introduced the award’s emotional presentation. Chris Rock hosted the 1999 VMAs and this happened 23 years before Smith slapped Rock onstage during the 94th Academy Awards.

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