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LIFE Picture Collection via Getty Images
A Star Is Born
Witherspoon was nominated for Best Performance by an Actress in a Motion Picture, Musical or Comedy, at the ceremony for her performance in Election.
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ONS/ZUMAPRESS.com
First Time Nominee
The actress, who donned a gorgeous strapless dress to the award show, was nominated alongside Janet McTeer, Julianne Moore, Julia Roberts, and Sharon Stone.
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LIFE Picture Collection via Getty Images
LOL
Witherspoon shared a laugh with photographers on the red carpet.
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AP Photo/Mark J. Terrill
Wave to Cameras
Witherspoon attended the ceremony with her then-husband, Ryan Phillippe.
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Frank Trapper/Corbis via Getty Images
A Walk Down Memory Lane
The actors first met in 1997, a few years before they starred in Cruel Intentions together.
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Steve Granitz/Getty Images
Red Carpet Couple
The duo, who tied the knot in 1999, share kids Ava and Deacon Phillippe.
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Berliner Studio / BEImages
After-Party
Phillippe and Witherspoon stopped by an after-party following the 2000 Golden Globes.