There was no shortage of pop culture moments in 2006.
Millennials were moving and grooving to Nelly Furtado's "Promiscuous" in the club, families awaited Taylor Hicks' victory in season five of American Idol and fans were lining up at the box office for tickets to Pirates of the Caribbean: Dead Man's Chest and Mission: Impossible III.
And in Hollywood, stars were buzzing with excitement to see who would take home a shiny new trophy at the Oscars. Indeed, with films like Brokeback Mountain, Capote and Munich up for gold during the 78th Academy Awards, celebs hit the red carpet in the most 2006 way possible.
It was an award season of bold colors, chiffon pieces and halter necklines. Keira Knightley—who was nominated in the Best Actress in a Leading Role category for Pride & Prejudice—stepped out in a Vera Wang burgundy taffeta gown, featuring a dramatic mermaid skirt and pleating along the top.
It was an evening to remember for Brokeback Mountain costars Heath Ledger and Michelle Williams—nominated for Best Actor in a Leading Role and Best Actress in a Supporting Role—as they made the annual ceremony a date night. The latter turned heads in her canary-yellow Vera Wang column dress, paired perfectly with a candy-apple-red lip.
That's not to say neutral colors weren't also in style, however. While Kiera and Michelle were visions in jewel tones, stars like Uma Thurman, Jennifer Garner and Jessica Alba sparkled in creams and beiges. In fact, the Kill Bill actress was angelic as she arrived in a white Versace number, complete with a sheer, ruched top and chiffon godet panels along the skirt.
Among the most memorable looks was Reese Witherspoon's 1955 Christian Dior silvery beaded gown. And fittingly so, the then-29-year-old ultimately won Best Actress in a Leading Role for Walk the Line.
And as Reese held her Oscar tightly, she paid homage to her character and style icon June Carter Cash.
"People used to ask June how she was doing, and she used to say: 'I'm just trying to matter,'" she reflected. "And I know what she means. I'm just trying to matter and live a good life and make work that means something to somebody. And you have all made me feel that I might have accomplished that tonight.”
As movie lovers wait to see who wins gold at the 2026 Oscars on March 15, keep reading for a look back at the award show 20 years earlier.
Reese Witherspoon
What, like looking good at the Oscars is hard? Not for Reese Witherspoon, who arrived in a 1955 Christian Dior silvery beaded gown. In fact, it was the perfect look for the Walk the Line star to wear as she won Best Actress in a Leading Role for the project.
Michelle Williams
The Brokeback Mountain star—who was nominated for the Best Actress in a Supporting Role—was anything but blue in her canary yellow Vera Wang gown.
Jessica Alba
The Fantastic Four actress was sweeter than honey in Versace.
Salma Hayek
The Frida star looked phenomenal from dusk till dawn in her show-stopping blue Versace look.
Ben Stiller
The Zoolander star knew how to look really, really, ridiculously good-looking with his blue steel pose.
Charlize Theron
The actress—who was nominated in the Best Actress in a Leading Role category for North Country—was ready to have a golden evening in this olive green Dior gown adorned with a statement bow on her shoulder.
Jennifer Garner
The 13 Going on 30 actress was electric as she sparkled in her butter yellow Michael Kors gown.
Heath Ledger
Jennifer Aniston
It's the one where the Friends alum hit the red carpet in a black fit and flare number from Rochas.
George Clooney
No heist needed for the Ocean's Eleven alum. After all, he arrived onto the red carpet in a classic suit before accepting the Best Actor in a Supporting Role trophy for his role as Bob Barnes in Syriana.
Keira Knightley
Keira Knightley—who was nominated in the Best Actress in a Leading Role category for Pride & Prejudice—proved she was a treasure in her burgundy Vera Wang gown.
Jennifer Lopez
Before the "Jenny From the Block" singer could get loud at the Vanity Fair afterparty, she stepped out in a vintage chartreuse Jean Dessès look.
Uma Thurman
Dancing like Uma Thurman is one thing, but embodying her style? Impossible. After all, the Pulp Fiction star looked ethereal in her pale Versace ensemble.
Jake Gyllenhaal
The evening was anything but dark for the Brokeback Mountain star, who was up for Best Actor in a Leading Role.