It is one of those frozen-in-time Hollywood moments. You know the one. It’s 1998, the 70th Academy Awards, and two young guys from Boston are jumping up and down on stage like they just won the lottery. Ben Affleck and Matt Damon had just secured the Oscar for Best Original Screenplay for Good Will Hunting. The camera pans to the audience, searching for the leading lady, the one who played Skylar and grounded the whole film.
There she is. Minnie Driver.
But she isn’t jumping. She isn't cheering with the same wild abandon as everyone else in the Shrine Auditorium. Instead, she looks... hollow. Her eyes are glassy. Her smile is the kind you put on when you’re trying to survive a car crash in slow motion. For twenty-five years, people speculated about that look. Was she just overwhelmed? Was she tired of the "Matt and Ben" show?
Nope. She was heartbroken. And she was watching her ex-boyfriend celebrate the biggest night of his life while sitting just a few rows away from his new girlfriend.
The Set of Good Will Hunting: Where It All Began
They met where most actors do—at work. In 1997, Matt Damon and Minnie Driver were at the absolute center of the cultural zeitgeist. Damon was the wunderkind writer and star; Driver was the established British talent who had already made waves in Circle of Friends.
The chemistry you see on screen between Will and Skylar? It wasn't just acting. It was real. "I was blown away by his commitment to me as an actor," Driver told The Telegraph years later. She admitted she fell for him hard—an "occupational hazard," as she put it.
But the road to that romance wasn't easy. Harvey Weinstein, the producer who looms over that era of film history like a shadow, actually didn't want Driver in the movie. He famously told the creators she wasn't "hot enough" for the part. Damon and Affleck, to their credit, fought for her. They knew she was the heartbeat of the story. That shared struggle, the "us against the world" mentality of an indie film turning into a juggernaut, created a bond that felt unbreakable.
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Until the world actually arrived.
The Oprah Interview: A Breakup Heard 'Round the World
If you think modern celebrity breakups are messy because of Instagram, you clearly didn't live through the late 90s. There were no "Notes app" apologies back then. There was just Oprah.
In early 1998, Matt Damon sat down with Oprah Winfrey. At this point, everyone assumed he and Minnie were still the "It" couple. A month earlier, he’d been on Letterman gushing about how she "rocked his world."
Then, the bombshell.
"Well, I'm single," Damon told Oprah. "I was with Minnie for a while, but we're not really romantically involved anymore."
Imagine being Minnie Driver. You’re at home, or maybe you’re out, and suddenly your phone starts blowing up because your boyfriend just told the most powerful woman in media—and millions of viewers—that you guys are done. Driver later called the move "fantastically inappropriate." Honestly? That’s putting it lightly. It was a brutal way to find out your relationship status had changed.
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What Most People Get Wrong About the 1998 Oscars
For decades, the narrative was that they had a "mutual" split before the awards. But thanks to some recent social media honesty from Driver herself, we know the truth is much grittier.
In late 2023, a clip of that Oscar win resurfaced on Instagram. Driver, now in her 50s and far past the need to protect anyone’s ego, hopped into the comments. She explained that Matt had ended things just a few weeks before the ceremony.
To make matters worse, he didn't show up alone. He was there with Winona Ryder.
So, when the camera cut to Minnie Driver during that iconic acceptance speech, she wasn't just "overwhelmed" by the film's success. She was a 25-year-old woman watching the man she loved win an Oscar while he was literally dating someone else in the same room. "I was devastated," she wrote. "Wish I could have celebrated more as it was an amazing moment for all of us."
Why Matt Damon and Minnie Driver Still Matters Today
It's easy to dismiss this as old gossip, but the Matt Damon and Minnie Driver story is actually a case study in the "folly of youth," as Driver calls it.
Damon was rocket-shipping into a level of fame that few people ever experience. He went from a struggling actor to an Oscar winner and a global sex symbol in the span of about eighteen months. When that happens, people often don't behave well. They get "tone deaf," as Driver pointed out decades later during the #MeToo movement when she called out Damon for some of his comments on sexual misconduct.
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But there’s a silver lining here.
In 2021, Driver revealed that she ran into Damon on a beach. It was the first time they’d spoken in twenty years. He was with his wife, Luciana Barroso, and their kids. Driver was there with her own family. They had what she described as a "middle-aged conversation" about the weather and life.
The heat was gone. The resentment had evaporated into the salt air.
Lessons from the Fallout
- Workplace Romance is High-Risk: As Driver’s family warned her at the time, dating a co-star during a "perfect storm" of fame is a recipe for disaster.
- The Medium Matters: Ending a relationship via a nationally televised talk show is never the right move, no matter how famous you are.
- Perspective is a Gift: Driver’s recent comments show that you can acknowledge the "agony" of a past version of yourself without letting it bitter your present.
If you find yourself looking back at a "combustible" ending in your own life, take a page from Minnie Driver’s book. She doesn't regret the "magic" of the Good Will Hunting era. She just wishes she could go back and give that 25-year-old girl a hug and tell her it was all going to be fine.
Because it was. She went on to have a massive career, a beautiful family, and the dignity of having stayed silent when she could have screamed. Damon, too, found stability far away from the tabloid-heavy romances of his youth.
Next Steps for the Nostalgic:
If you want to see the performance that started it all, re-watch the "Skylar at the outdoor cafe" scene in Good Will Hunting. It remains one of the most raw, vulnerable pieces of acting from that decade—made even more poignant knowing now exactly what was happening behind the scenes. You can also pick up Driver's memoir, Managing Expectations, where she dives deeper into the reality of being "the wronged woman" in the eyes of the 90s press.