What The Stars Wore To The Oscars 20 Years Ago

By Shayna Spero

February 5, 2020

20 years ago, the Oscars red carpet at The Shrine Auditorium was filled with stars like Angelina Jolie, Denzel Washington, 2000s Hollywood golden couple Jennifer Aniston and Brad Pitt and mega popular boyband, *NSYNC. While it seemed as if fitted gowns and plunging necklines were the fashion theme of the night, stars like Hilary Swank, who took home an Oscar for Best Actress that year, stunned in ballgowns.

As we approach the first Academy Awards ceremony of the decade this Sunday (February 9), we'd like to take a look back at the red carpet style 20 years ago. From Angelina's formfitting gothic look, to Charlize Theron's chic orange gown, find out what the rest of the stars wore on the Oscars red carpet in 2000 below!

Angelina Jolie

Winona Rider

Cate Blanchett

Jennifer Aniston and Brad Pitt

Tom Green and Drew Barrymore

Gwenyth Paltrow

Salma Hayek

Tyra Banks

*NSYNC

Nicole Kidman

Cameron Diaz

Lucy Liu

Ethan Hawke and Uma Thurman

Heather Graham

Charlize Theron

Hilary Swank

Dame Judi Dench

Jude Law and Sadie Frost

Garth Brooks and Sandy Mahl

Haley Joel Osment

Erykah Badu

Gloria Estefan

Denzel Washington and Pauletta Washington

Angela Bassett

Photos: Getty Images

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