See Your Favorite Stars' Golden Globes Looks From 20 Years Ago for the Ultimate Fashion Flashback

See what Gwyneth Paltrow, Halle Berry, Julia Roberts, Reese Witherspoon, Cameron Diaz, Matt Damon and more stars wore to the 2000 Golden Globes.

By Elyse Dupre Jan 04, 2020 1:00 PMTags
Watch: 2020 Golden Globes: By the Numbers

It's almost time for the 77th Annual Golden Globe Awards! 

The award show takes place Sunday, Jan. 5 at The Beverly Hilton in Beverly Hills, Calif. Ricky Gervais is hosting the big event for the fifth time in his career.

Marriage Story is the most-nominated film of the night with a total of six nods. However, The Irishman and Once Upon a Time…in Hollywood follow closely behind with five nominations apiece. As for TV's top contenders, Chernobyl, The Crown and Unbelievable lead the pack with four nods each. 

Of course, the event isn't just about the accolades. There's also the star-studded fashion. If the red carpets of the past are any indication, viewers can expect to see some showstopping looks. They can also look forward to seeing how stars' styles have evolved. 

In honor of the 2020 Golden Globe Awards, here's a look back at celebrities' 2000 looks and how their styles have changed over the last 20 years.

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Enjoy the blast from the past!

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.