1. Britney Spears and NSYNC — “…Baby One More Time”/ “Tearin’ Up My Heart” 
In their VMA debut performance the guys shared the stage with Britney Spears — who also happened to be making her first appearance.
2. “This I Promise You”/ “Bye, Bye, Bye”/ “It’s Gonna Be Me” 
The guys gave an iconic performance of hits from their then-latest album No Strings Attached.
Unfortunately, their video for “Bye Bye Bye” did not win Video of the Year that night — it lost to Eminem’s “The Real Slim Shady.” But the guys didn’t leave empty handed, their video took home the Moonman for Best Pop Video, Best Choreography in a Video, and Viewer’s Choice.
NSYNC stole the show that night by bringing on none other the “King of Pop,” Michael Jackson, during their performance of “Pop.”
Also, check out Justin Timberlake beat-boxing in the background.