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Minnie Driver Revealed the Gossipy Reason Why She Looked So Sad at the 1998 Oscars

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Minnie Driver is reliving 1998 gossip history, and she’s spilling a bit of the tea. A clip of Ben Affleck and Matt Damon‘s Best Original Screenplay win for Good Will Hunting recirculated on Instagram this week, and the now-53-year-old actress decided to chime in with her thoughts on the 25-year-old Hollywood story.

Her first comment under the post was a simple response. “My face 😂😂😂😂❤️,” she wrote. In the clip, Driver looked rather bittersweet at Damon and Affleck on the stage, exuberantly accepting their award. It was Affleck who praised her for her “brilliant” work in the film, but, at the time, she probably would have preferred the acknowledgment came from Damon. The couple was dating just weeks prior to the ceremony, and it’s alleged that he dumped her while live on the air on The Oprah Winfrey Show. 

A fan chimed in with their thoughts on the clip, adding, “Minnie looks so sad.” And leave it to Driver to give everyone the 25-year-old response we’ve all been waiting for. She responded under the comment, “Matt had ended our relationship a few weeks before this, and was at the Oscars with his new gf … I was devastated,” she wrote. “Wish I could have celebrated more as it was an amazing moment for all of us, and for this wonderful film! ♥️.”

And who was that rumored new girlfriend? Likely Winona Ryder, who dated Damon almost immediately after Driver. She was part of a power group foursome that included her, Damon, Affleck, and his then-girlfriend Gwyneth Paltrow. It’s a wild group to think of now since they are all in different places in their lives, but the paparazzi sure had some fun when they were out on the town together. 

Driver spoke about the awkward event to Entertainment Tonight in 2022, calling it a “strange, surreal dream.” The ABC cameras were aimed at her all night, so she kind of knew the Oscars producers were looking for some good television. She recalled, “[The cameraman] was just waiting for the moment that I was going to break, or something was going to happen, or I was going to get up and scream. He’d been told, ‘Stay on her, bud. Something’s gonna happen.’” But Driver isn’t out for revenge over two decades later, she only has sweet things to say about Damon now. Driver noted, “That was just a sweet romance that was just a sweet love affair in the center of all that stuff, but had a combustible ending, which then became the focus.”

Before you go, click here to see all the most shocking Oscars looks over the years.

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