Flashback! See Britney Spears, Cher and More at the 1999 American Music Awards

Relive the show where N'SYNC, Britney Spears and more pop stars dominated the red carpet at the 1999 American Music Awards

By Cydney Contreras Nov 21, 2019 1:00 PMTags
Watch: American Music Awards 2019: By The Numbers

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 SpearsN'SYNCBackstreet Boys and more musicians represented the pop music area, while Shania Twain and 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?

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To take a trip down memory lane, check out the gallery below!


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

Dixie Chicks

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

Whitney Houston

And IIIII will always love this purple and black coat. 

98 Degrees

We say "I Do" to this boy band's red carpet appearance. 

Paula Abdul

The former American Idol judge is "Straight Up" killing it in this all pink ensemble.

LeAnn Rimes & Celine Dion

Name a more iconic duo. We'll wait

Celine Dion


Carmen Electra

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

Will Smith & Jada Pinkett Smith

This family photo is something we will (red table) talk about until the end of time.


Frosted tips for the win.

Melissa Joan Hart

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

Britney Spears

"Gimme More" red carpet looks as angelic as this.

Garth Brooks & KISS

These stars clearly wanted to rock and roll all nite.

Backstreet Boys

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

Boy George & Enrique Iglesias

The U.K. meets Spain with these two pop stars.

Jennifer Love Hewitt

Who else had a stylish red choker like this?

Tia & Tamera Mowry

Talk about a blast from the past.

Stephan Jenkins & Charlize Theron

Third Eye Blind lead singer brings the famous actress as his date to the show.

Bill Maher & Snoop Dogg

These two always know how to drop it like it's hot.


Animal print never goes out of style.