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 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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Emily Robison, Natalie Maines, Martie Maguire, Dixie Chicks

Ron Galella/Ron Galella Collection via Getty Images

Whitney Houston


98 Degrees

Vinnie Zuffante/Getty Images

Paula Abdul

Jim Smeal/Ron Galella Collection via Getty Images

LeAnn Rimes, Celine Dion


Celine Dion

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Carmen Electra

Ron Galella, Ltd./Ron Galella Collection via Getty Images

Will Smith, Jada Pinkett


NSYNC, Joey Fatone, Justin Timberlake, Chris Kirkpatrick, Lance Bass, JC Chasez

Ron Galella, Ltd./Ron Galella Collection via Getty Images

Melissa Joan Hart


Britney Spears

Jeff Kravitz/FilmMagic, Inc

Garth Brooks, Kiss


The Backstreet Boys

Frank Trapper/Corbis via Getty Images

Boy George, Enrique Iglesias

Ron Galella, Ltd./Ron Galella Collection via Getty Images

Jennifer Love Hewitt

Steve Granitz Archive 1/WireImage

Tia Mowry, Tamera Mowry

Patrick McMullan/Getty Images

Stephan Jenkins, Charlize Theron

Barry King/WireImage

Bill Maher, Snoop Dogg

Jeff Kravitz/FilmMagic


Ron Wolfson/Getty Images

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