Reese Witherspoon
The actress was up for her first Golden Globe that year. She was nominated in the Best Performance by an Actress in a Motion Picture (Musical or Comedy) category for her role in Election.
Gwyneth Paltrow
The brunette beauty posed for pictures in a yellow top and black pants. She also rocked some serious bling. Paltrow won a Golden Globe for her performance in Shakespeare in Love the year before.
Halle Berry
The Introducing Dorothy Dandridge star turned heads in this red and white number and won the award in the Best Performance by an Actress in a Limited Series or a Motion Picture Made for Television category.
Matt Damon & Winona Ryder
That year, Damon was nominated in the Best Performance by an Actor in a Motion Picture (Drama) category for his work in The Talented Mr. Ripley. Ryder joined him at the event; however, the former couple broke up later that year.
Angelina Jolie
2000 was the third year in a row Jolie won a Golden Globe. That year, she took home the trophy for her work in Girl, Interrupted.
Hugh Grant & Elizabeth Hurley
The actor was nominated for a Golden Globe that year for his role in Notting Hill. While he brought Hurley as his date, the two split later that year.
Julia Roberts
Speaking of Notting Hill, the actress was also up for a trophy for her role in the film. She looked ravishing in red at the award show.
Catherine Keener & Cameron Diaz
The Being John Malkovich co-stars smiled from ear to ear on the red carpet—and for good reason. Not only did they both earn Golden Globe nominations but the movie also secured a nod.
Denzel Washington
The Hurricane celeb looked dapper in his suit and won the award in the Best Performance by an Actor in a Motion Picture (Drama) category.
Tom Cruise & Charlize Theron
The Magnolia star was all smiles as he posed alongside Theron and held his trophy for Best Performance by an Actor in a Supporting Role in any Motion Picture.
Sarah Jessica Parker
It was no surprise that the Sex and the City star hit the red carpet in style. She also took home the trophy that year in the Best Performance by an Actress in a Television Series (Musical or Comedy) for her role as Carrie Bradshaw.
Penélope Cruz
Cruz wowed in white at the big award show.
Hilary Swank
Swank won the Golden Globe that year in the Best Performance by an Actress in a Motion Picture (Drama) category for her role in Boys Don't Cry.
Keri Russell
The Felicity star looked pretty in pink at the 57th Annual Golden Globe Awards.
Meryl Streep
That year, the actress was nominated for Best Performance by an Actress in a Motion Picture (Drama) for her role in Music of the Heart.
Meg Ryan
The actress opted for a fitted gray shirt and a sunny yellow skirt for the red carpet.
Angela Bassett
Bassett glimmered in gold on the red carpet.
Jim Carrey & Renée Zellweger
As fans will recall, the Me, Myself & Irene co-stars briefly dated before calling it quits later that year.
Natalie Portman
That year, the celebrity was up for Best Performance by an Actress in a Supporting Role in any Motion Picture for her work in Anywhere But Here.
Jennifer Love Hewitt
The actress dazzled in a sparkly number on the red carpet.