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Minnie Driver Just Revealed Why She Looked "Devastated" When Ex Matt Damon Won His Oscar

The two actors dated after meeting on the set of Good Will Hunting.

The 1998 Academy Awards were a huge night for the team behind Good Will Hunting. The film was up for nine awards, including Best Picture, and ended up winning two: Best Supporting Actor for Robin Williams and Best Original Screenplay for Matt Damon and Ben Affleck. (To refresh your memory, the even bigger winner of the ceremony was Titanic.) The screenplay award was considered an upset, as Good Will Hunting was the first script by Damon and Affleck, who were both in their 20s at the time. When the friends took to the stage, they gave a joyful, enthusiastic speech that remains one of the evening's most memorable moments. But one person looking on from the audience didn't seem too happy: Good Will Hunting co-star and Damon's ex Minnie Driver, who just opened up on social media about what she was feeling when it happened.

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In an Instagram comment, Driver addressed why she looks upset in a clip of their acceptance that includes the audience's reaction. In October, the Instagram account @movieshmood posted a video of Affleck and Damon's speech that also shows some of their co-stars and director Gus Van Sant watching from the crowd. When the clip flashes to Driver, she is not smiling. The account @commentsbycelebrities pointed out in a recent post that Driver commented, "My face" with four crying-laughing emoji and a heart, on the @movieshmood video.

Another Instagram user commented, "Minnie looks so sad."

"Matt had ended our relationships a few weeks before this, and was at the Oscars with his new gf… I was devastated," Driver, who was nominated for Best Supporting Actress for Good Will Hunting, wrote in reply to that comment. "Wish I could have celebrated more as it was an amazing moment for all of us, and for this wonderful film!"

Damon and Driver met when they started filming Good Will Hunting and began dating. But, the relationship came to an end before the movie was honored at the Oscars. According to Driver, Damon announced their split when he was on The Oprah Winfrey Show, which was reportedly the first she'd heard of it.

"It's unfortunate that Matt went on Oprah; it seemed like a good forum for him to announce to the world that we were no longer together, which I found fantastically inappropriate," Driver told the Los Angeles Times in July 1998. "Of course, he was busy declaring his love for me on David Letterman a month previously."

It seems that the girlfriend Driver referred to in her Instagram comment was Winona Ryder. While Damon and Ryder were not photographed together at the Oscars, she was at the Vanity Fair Oscar Party that year, and they were photographed at the Miramax Films Pre-Oscar Party. The actors are known to have started dating around this time before breaking up in 2000.

Matt Damon and Winona Ryder at the Miramax Films Pre-Oscar Party in 1998
Jim Smeal/Ron Galella Collection via Getty Images

As for Damon's date to the actual show, that was his mother, Nancy Carlsson-Paige. In an April 2023 video for Vanity Fair, Damon and Affleck looked back on their awards show evening. "I remember how everyone had made such a big thing out of it as if this was such a novelty," Affleck said of them bringing their mothers. "And I remember thinking, being insecure, like, 'Why? Why is it weird that we're bringing our moms?' Like, 'Who else do you think we would bring?'"

Driver and Damon have both long moved on from their split, which happened 25 years ago. On a 2021 episode of the podcast Keep It! (via Today), Driver said that she had run into Damon more recently. "That was last summer and it was actually very nice to see him, and his kids, and his wife and it all felt quite middle-aged actually, which was reassuring," she said. "I feel like so much of the folly of youth went on with our initial relationship, like it was amazing and tabloid-y. So that was nice to just have sort of a middle-aged conversation about the weather and stuff."

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Lia Beck
Lia Beck is a writer living in Richmond, Virginia. In addition to Best Life, she has written for Refinery29, Bustle, Hello Giggles, InStyle, and more. Read more
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