25 Years Later: The 5 Most Shocking And Iconic Moments Of The 2000 MTV Video Music Awards

The 2000 MTV Video Music Awards (VMAs) was not just an awards show; it was a cultural flashpoint that defined the transition into the new millennium. Held on September 7, 2000, at the legendary Radio City Music Hall in New York City, the ceremony—hosted by the Wayans brothers, Marlon Wayans and Shawn Wayans—delivered a chaotic, unpredictable, and ultimately unforgettable night of pop culture history. From a controversial performance that sparked global conversation to an unprecedented sweep by a rap icon, the 2000 VMAs solidified its place as one of the most significant and talked-about nights in music television, with its moments still being revisited and analyzed as of today, December 14, 2025. The event perfectly captured the raw energy and boundary-pushing spirit of the era, showcasing the biggest names in pop, hip-hop, and rock. While Eminem dominated the winner's list, the night’s legacy is truly cemented by a single, daring performance that challenged the conservative norms of the time and launched a new, bolder image for a pop princess. Revisiting the 2000 VMAs is a journey back to the peak of Y2K celebrity, fashion, and musical dominance.

The Definitive List of 2000 MTV VMA Winners and Nominees

The 2000 VMAs was a night of clear winners, with two artists, Eminem and Aaliyah, taking home the biggest genre awards. The nominations were a perfect snapshot of the diverse music landscape at the turn of the millennium, featuring pop titans, hip-hop legends, and rock favorites.

Eminem's Domination and Major Awards

The undisputed champion of the night was the Detroit rapper, Eminem, whose video for "The Real Slim Shady" was a critical and commercial phenomenon. His success was a clear indication of hip-hop's growing mainstream power.

• Video of the Year (Winner): Eminem – "The Real Slim Shady"
• Best Male Video (Winner): Eminem – "The Real Slim Shady"
• Best Rap Video (Winner): Eminem – "Forgot About Dre" (with Dr. Dre)
• Video of the Year (Nominees):
  • Britney Spears – "Oops!... I Did It Again"
  • *NSYNC – "Bye Bye Bye"
  • Rage Against the Machine – "Sleep Now in the Fire"
  • Christina Aguilera – "What a Girl Wants"

Key Winners Across All Categories

The awards also recognized the incredible talent of R&B, pop, and rock artists who were defining the sound of 2000.

• Best Female Video (Winner): Aaliyah – "Try Again"
• Best Group Video (Winner): blink-182 – "All the Small Things"
• Best Pop Video (Winner): *NSYNC – "Bye Bye Bye"
• Best New Artist in a Video (Winner): Macy Gray – "I Try"
• Best R&B Video (Nominees):
  • TLC – "Unpretty" (Winner)
  • Destiny's Child – "Say My Name"
  • Sisqó – "Thong Song"
• Breakthrough Video (Winner): Björk – "All Is Full of Love"

The Performance That Changed Pop: Britney's Nude Bodysuit Controversy

The most talked-about moment of the 2000 MTV Video Music Awards—and arguably one of the most iconic performances in VMA history—belonged to Britney Spears.

"Oops!... I Did It Again" and the Stripping Reveal

Britney Spears took the stage to perform her smash hit, "Oops!... I Did It Again." The performance began with the global pop star wearing a conservative, full-coverage black suit and fedora, a stark contrast to her bubbly, schoolgirl image. In a choreographed move that shocked the live audience and viewers worldwide, she dramatically stripped off the suit to reveal a flesh-colored, nude-toned, two-piece outfit. This "nude bodysuit" was instantly controversial, sparking intense media coverage and public debate over her image and sexuality.

Other Unforgettable Stage Moments

While Britney’s performance was the most controversial, the night was packed with high-energy sets from other major artists.

• Eminem's Army: Eminem performed "The Real Slim Shady" with an army of look-alikes, creating a truly memorable visual moment that reinforced his anti-establishment brand.
• Christina Aguilera's Medley: Christina Aguilera delivered a powerful medley of her hits "Genie in a Bottle" and "Come On Over," showcasing her vocal prowess.
• Red Hot Chili Peppers: The rock legends performed "Californication," bringing a necessary dose of alternative rock energy to the pop-heavy show.
• Janet Jackson's Tribute: Janet Jackson performed "Doesn't Really Matter," adding a layer of sophisticated R&B to the evening's line-up.
• blink-182's Chaos: The punk-pop band blink-182 brought their signature irreverence to the stage, performing "All the Small Things."

Y2K Glamour: The Most Iconic Red Carpet Fashion Statements

The red carpet at the 2000 VMAs was a showcase of late 90s/early 2000s fashion, featuring daring, experimental, and sometimes polarizing looks that have become legendary in retrospect.

The Daring and the Defining Looks

The red carpet fashion perfectly encapsulated the Y2K aesthetic, blending high-fashion glamour with pop-star audacity.

• Jennifer Lopez's White Ensemble: Jennifer Lopez arrived with Sean "Puffy" Combs in a stunning, all-white outfit that exuded pure star power and cemented her status as a fashion icon of the era.
• Destiny's Child's Coordinated Style: The trio of Beyoncé, Kelly Rowland, and Michelle Williams showcased their signature coordinated style, wearing matching, yet distinct, hip-hop-inspired ensembles that were true to their "Say My Name" era.
• Pink's Sea Urchin Dress: The then-emerging artist Pink wore a truly unique, sea urchin-inspired pink dress, an early indicator of her willingness to challenge fashion norms and embrace controversy.
• Gisele Bündchen's Chic Debut: Supermodel Gisele Bündchen made her VMA debut in a sophisticated, form-fitting black turtleneck gown, offering a moment of understated elegance amidst the chaos.
• Sisqó's "Thong Song" Statement: Sisqó, nominated for his massive hit "Thong Song," arrived in an outfit that was as memorable as his music, featuring a metallic sheen and bold accessories.

The 2000 MTV Video Music Awards remains a cultural touchstone because it was a moment where the music, the fashion, and the celebrity culture of the new decade collided in an explosion of unforgettable moments. From Eminem's lyrical genius to Britney Spears' controversial reinvention, the night at Radio City Music Hall was a true masterclass in pop spectacle.