Gwyneth Paltrow Reflects on Oscar Upsets and Why Awards Are Ultimately Subjective

More than 25 years after one of the Oscars’ most debated outcomes, Gwyneth Paltrow is looking back on the night Shakespeare in Love beat Saving Private Ryan—and sharing why she believes awards are never as clear-cut as people want them to be.

At the 71st Academy Awards in 1999, Shakespeare in Love shocked many viewers by winning Best Picture over Saving Private Ryan, which had been widely expected to take the top prize. The romantic comedy went on to win seven Oscars, including Best Actress for Paltrow, while Steven Spielberg won Best Director for his World War II epic. The split decision immediately sparked controversy—and it’s a debate that still comes up today.

Speaking on The Awardist with host Gerrad Hall, Paltrow was asked whether she and Spielberg—who is also her godfather—have ever discussed the upset. While she didn’t dive into details, she recalled the irony of that night: Spielberg won for directing, and she won for acting.

“Steven had already been at this rodeo for a very long time,” she said, adding that even back then, he was no stranger to awards-season highs and lows.

Paltrow used the conversation to zoom out and talk about the Oscars more broadly, calling the process “arbitrary” and impossible to predict. To make her point, she referenced the infamous La La Land and Moonlight mix-up at the 2017 ceremony, when the wrong Best Picture winner was announced onstage.

“Both of those could have won,” Paltrow said, noting that moments like that prove how subjective awards really are.

She also described awards as more than just recognition. In her view, they are part of a larger business system that helps keep the film industry moving. Even being part of the conversation, she said, can be a win—bringing attention, audiences, and financial support to movies that might otherwise struggle to survive.

“There’s always going to be debate about what people like and don’t like,” Paltrow explained. “Art is subjective. That’s the point.”

Paltrow is now back in the awards spotlight with Marty Supreme, directed by Josh Safdie. In the film, she plays Kay Stone, a wealthy socialite and fading movie star who forms an unexpected bond with a young ping-pong prodigy played by Timothée Chalamet.

Whether or not Marty Supreme takes home trophies, Paltrow seems at peace with whatever the outcome may be—seeing awards not as final judgments, but as one small part of a much bigger, emotional conversation about art.