Rocking this gorgeous orange and pink masterpiece, our 2000 pop princess won Album Artist of the Year for her second studio album, Oops!... I Did It Again, which included hit singles like "Stronger" and of course, "Oops!... I Did It Again."
Not to be defined by the artist's iconic name, Pink sported a rainbow pixie cut up top and a dress with flowing dollar bills while collecting her award for New Female Artist of the Year. Her dress was certainly a good prediction for the singer's bright future!
Owning her chic feathered hair cut with a trendy dip dye, this genie left her bottle to snag the award for Female Artist of the Year. In 2000, she was renowned for singles like "What a Girl Wants."
In the midst of 2000, we had no doubt this group would make a red carpet appearance! Slaying the runway, this band was trending with the release of their second album, Return of Saturn. Hi Gwen Stefani!
Still a popular track today, SisQó celebrated six wins at the 2000 Billboards including Male Artist of the Year, New Male Artist of the Year, R&B/Hip-Hop Male Artist of the Year, R&B Hip Hop Singles Artist of the Year, New R&B Hip Hop Singles Artist of the Year and Hot 100 Singles Male Artist of the Year for the iconic tune "Thong Song."
Just the first of several appearances for these three leading ladies, the red carpet was not ready for these gorgeous gowns. Of course, this photo was taken before slaying their live performance and taking some awards home later. We see you ladies!
We hope these coats make an appearance this winter! The No Strings Attached group shut down the awards show with their rendition of "Just Got Paid" before going home with Albums Artist of the Year (Duo/Group), Album of the Year and Top 40 Artist of the Year.
Stepping in sync and in the same pattern, these ladies took home four awards for their album, The Writings on The Wall: Hot 100 Singles Duo or Group of the Year, Hot 100 Singles Artist of the Year, Duo/Group of the Year and the highest award of the evening, Artist of the Year.
Just 17-years-old at the time, Mila joined her co-stars Wilmer, who played Fez, and Danny, who played Hyde, on the popular sitcom That 70's Show for a stroll down the red carpet. The show was in the middle of its third season. We only have one question: Where's Ashton?
Coming out of the ceiling in a giant cage, these ladies had a message: They cannot be tamed! Singing some of their top singles including "Independent Women," "Say My Name" and "Jumpin' Jumpin," these ladies were serving fierceness for four minutes straight.
Still at the beginning of her long career, the "Un-Break My Heart" singer walked away with R&B/Hip Hop Female Artist of the Year.
In 2000, long before A Walk to Remember stole our hearts, this triple threat placed in the Billboard Top 40 with her song, "I Wanna Be With You." We want to be with you too, Mandy!
Oh my god, they're back again! This Backstreet Boy member and his younger brother made their red carpet entrance with some personality. Check out those frosted tips!
The lead singer of the popular rock band Matchbox Twenty was not only celebrating the release of his second album, Mad Season, which charted top three on the Billboard 200. He also completed a year of marriage with his wonderful wife. Ah, young love!