The 2019 American Music Awards are right around the corner, but first we’re taking a detour down memory lane.
In advance of the annual show and red carpet, it only seems right to revisit one of the most historic nights in award show history: the 1999 American Music Awards. It was a night that saw numerous stars from basically ever genre in music. Britney Spears, N’SYNC, Backstreet Boysand more musicians represented the pop music area, while Shania Twainand Garth Brooks to serve as the country music crowd.
Plus, the red carpet fashion in itself deserves to be remembered. As the ’90s drew to a close and the ‘aughts were ushered in, new and unforgettable styles were beginning to emerge. Funnily enough, 20-years later those same trends are beginning to be en mode once again.
Then, there’s the music, which has pretty much ingrained itself in America’s culture. Who can forget the iconic Big Willie Style album from Will Smith?
To take a trip down memory lane, check out the gallery below!

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Cher
If we could turn back time, we’d go back to 1999 to witness this red carpet lewk in real life.

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Dixie Chicks
These country singers are blowin’ us away with their ’90s chic red carpet ensembles.

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Whitney Houston
And IIIII will always love this purple and black coat.
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98 Degrees
We say “I Do” to this boy band’s red carpet appearance.

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Paula Abdul
The former American Idol judge is “Straight Up” killing it in this all pink ensemble.

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LeAnn Rimes & Celine Dion
Name a more iconic duo. We’ll wait
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Celine Dion

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Carmen Electra
The Baywatch star proves her bombshell status on the red carpet.

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Will Smith & Jada Pinkett Smith
This family photo is something we will (red table) talk about until the end of time.
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NSYNC
Frosted tips for the win.

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Melissa Joan Hart
The Sabrina the Teenage Witch star makes a bewitch-ing appearance.

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Britney Spears
“Gimme More” red carpet looks as angelic as this.
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Garth Brooks & KISS
These stars clearly wanted to rock and roll all nite.

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Backstreet Boys
These boys were living larger than life on the 1999 AMAs red carpet.

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Boy George & Enrique Iglesias
The U.K. meets Spain with these two pop stars.
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Jennifer Love Hewitt
Who else had a stylish red choker like this?

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Tia & Tamera Mowry
Talk about a blast from the past.

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Stephan Jenkins & Charlize Theron
Third Eye Blind lead singer brings the famous actress as his date to the show.
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Bill Maher & Snoop Dogg
These two always know how to drop it like it’s hot.

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Brandy
Animal print never goes out of style.