The last year of the 20th century and the MTV VMAs had one of its most unforgettable nights on September 7, 2000. The VMAs were back at Radio City Music Hall in New York and MTV put comedians Shawn and Marlon Wayans in charge of the show. They were a riot but it definitely wasn’t them that stole the limelight at the 2K VMAs. Eminem walked away with three awards including the Best Male Video and Video of The Year and even pulled out a bottle of pills (mistakenly) when reaching inside his pockets for his acceptance speech. He definitely got around to scaring quite a few of the audience when he walked into the hall performing and followed by hundreds of clones who all wore his signature blue jeans and white tees and had cropped blond hair. NSYNC won the Viewer’s Choice award for Bye Bye Bye and Macy Gray rightfully got her Best New Artist award for I Try.

Britney Spears made her mark with her flesh colored outfit that was beneath the tuxedo that came off approximately 40 seconds into her routine. Performers included, Rage Against the Machine, Sisqo, Red Hot Chili Peppers, Blink-182, and the unlikely pairing of Christina Aguilera and Limp Bizkit's Fred Durst. The truth said, the show stopper of the nightwas Rage Against The Machine bassist Tim Commerford who climbed up the scaffolding of the set and wouldn’t come down even after the audience chanted “Jump”. Well for all his efforts to make the night a memorable one he got arrested and spent a night in prison. The last year of the century and the VMAs got bolder than ever.

List of Nominees and Winners at the MTV Video Music Awards 2000

Video of the Year

  • Eminem - The Real Slim Shady
  • blink-182 - All The Small Things
  • D'Angelo - Untitled (How Does It Feel)
  • NSYNC - Bye Bye Bye
  • Red Hot Chili Peppers – Californication
Winner: Eminem - The Real Slim Shady

Best Male Video

  • Eminem - The Real Slim Shady
  • D'Angelo - Untitled (How Does It Feel)
  • Kid Rock - Cowboy
  • Ricky Martin - Shake Your Bon Bon
  • Moby - Natural Blues
Winner: Eminem - The Real Slim Shady

Best Female Video

  • Aaliyah
  • Christina Aguilera - What A Girl Wants
  • Toni Braxton - He Wasn't Man Enough
  • Macy Gray - I Try
  • Britney Spears - Oops!...I Did It Again
Winner: Aaliyah

Best Group Video

  • blink-182 - All The Small Things
  • Dave Matthews Band - I Did It
  • Foo Fighters - Learn To Fly
  • NSYNC - Bye Bye Bye
  • Red Hot Chili Peppers – Californication
Winner: NSYNC - Bye Bye Bye

Best Pop Video

  • NSYNC - Bye Bye Bye
  • Christina Aguilera - What A Girl Wants
  • blink-182 - All The Small Things
  • Destiny's Child - Say My Name
  • Britney Spears - Oops!...I Did It Again
Winner: NSYNC - Bye Bye Bye

Best Rap Video

  • Dr. Dre f/ Eminem
  • DMX - Party Up
  • Eminem - The Real Slim Shady
  • Eve f/ Faith Evans - Love Is Blind
  • Jay-Z f/ U.G.K. - Big Pimpin'
Winner: Dr. Dre f/ Eminem

Best R&B Video

  • Destiny's Child - Say My Name
  • Toni Braxton - He Wasn't Man Enough
  • D'Angelo - Untitled (How Does It Feel)
  • Brian McKnight - Back At One
Winner: Destiny's Child - Say My Name

Best Hip-Hop Video

  • Sisqó - Thong Song
  • Lauryn Hill - Everything Is Everything
  • Juvenile - Back That Thang Up
  • Limp Bizkit f/ Method Man - N 2gether Now
  • Q-Tip - Vivrant Thing
Winner: Sisqó - Thong Song

Best Dance Video

  • Jennifer Lopez - Waiting For Tonight
  • Ricky Martin - Shake Your Bon Bon
  • NSYNC - Bye Bye Bye
  • Sisqó - Thong Song
  • Britney Spears - You Drive Me (Crazy)
Winner: Jennifer Lopez - Waiting For Tonight

Best Rock Video

  • Limp Bizkit - Break Stuff
  • Creed - Higher
  • Kid Rock - Cowboy
  • KoRn - Falling Away From Me
  • Metallica - I Disappear
  • Rage Against The Machine - Sleep Now in the Fire
Winner: Limp Bizkit - Break Stuff

Viewer's Choice

  • NSYNC - Bye Bye Bye
  • Christina Aguilera - What A Girl Wants
  • Eminem - The Real Slim Shady
  • Sisqó - Thong Song
  • Britney Spears - Oops!...I Did It Again
Winner: NSYNC - Bye Bye Bye

Best New Artist

  • Macy Gray
  • Christina Aguilera - What A Girl Wants
  • Papa Roach - Last Resort
  • Pink - There You Go
  • Sisqó - Thong Song
Winner: Macy Gray

Breakthrough Video

  • Björk - All Is Full Of Love
  • Blur - Coffee & TV
  • Nine Inch Nails - Into The Void
  • Supergrass - Pumping On Your Stereo
Winner: Björk - All Is Full Of Love

Best Video From A Film

  • Aaliyah
  • Aimee Mann - Save Me
  • Metallica - I Disappear
  • R.E.M. - The Great Beyond
  • Sisqó - Thong Song
Winner: Red Hot Chili Peppers - Californication

Best Direction

  • Red Hot Chili Peppers - Californication
  • D'Angelo - Untitled (How Does It Feel)
  • Eminem - The Real Slim Shady
  • Foo Fighters - Learn To Fly
  • Lauryn Hill - Everything Is Everything
Winner: Red Hot Chili Peppers - Californication

Best Choreography

  • NSYNC - Bye Bye Bye
  • Aaliyah - Try Again
  • Christina Aguilera - What A Girl Wants
  • Jennifer Lopez - Waiting For Tonight
  • Alanis Morissette - So Pure
Winner: NSYNC - Bye Bye Bye

Best Special Effects

  • Björk - All Is Full Of Love
  • Lauryn Hill - Everything Is Everything
  • Metallica - I Disappear
  • Red Hot Chili Peppers - Californication
  • Supergrass - Pumping On Your Stereo
Winner: Björk - All Is Full Of Love

Best Art Direction

  • Red Hot Chili Peppers - Californication
  • Filter - Take A Picture
  • Macy Gray - Do Something
  • Supergrass - Pumping On Your Stereo
Winner: Red Hot Chili Peppers - Californication

Best Editing

  • Aimee Mann - Save Me
  • Blaque - I Do
  • Eminem - The Real Slim Shady
  • Metallica - I Disappear
  • R.E.M. - The Great Beyond
Winner: Aimee Mann - Save Me

Best Cinematography

  • Macy Gray
  • Filter - Take A Picture
  • Madonna - American Pie
  • Metallica - I Disappear
  • Stone Temple Pilots - Sour Girl
Winner: Macy Gray