In 1998, the world was introduced to a pair of shy actors-turned-filmmakers who had just made their first Oscar-winning project.
It was 25 years ago, and Matt Damon and Ben Affleck weren’t quite yet the household names we know and love today.
Damon, then 27, and Affleck, 25, were hot off the heels of Good Will Hunting, a film they had co-written and starred in when they lived together as roommates.
Good Will Hunting, which also starred the late comedy legend Robin Williams, was lauded as a box office hit and critically acclaimed when it was released in 1997.
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But it wasn’t the first time the Hollywood powerhouse duo had worked together.
Affleck and Damon had first met in the 1980s as children in their hometown of Cambridge, Massachusetts. They went to the same high-school and their careers soon followed a very similar trajectory.
I remember thinking, being insecure, like, ‘Why? Why is it weird that we’re bringing our mums?
In 1989, they both starred in their first film together: Field of Dreams, which also featured Kevin Costner.
As the ’90s progressed, the former school mates continued to star in the same projects, including School Ties in 1992 and Glory Daze in 1995.
Though it was their joint project Good Will Hunting, written as they briefly lived together, that catapulted them both into international stardom.
It was art imitating life as Damon played the title character of Will and Affleck played his best friend, Chuckie.
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The movie was a smash-hit and went on to earn the pair an Oscar for Best Original Screenplay in 1998.
This was Damon and Affleck’s very first Oscars ceremony and it thrust them into the entertainment world stage.
If you needed further proof these young actors were still on the cusp of A-list success, they both actually brought their mothers as their dates to the 1998 Oscars.
The men both arrived on-stage and gave the first of many acceptance speeches in their careers.
“I just said to Matt, ‘Losing would suck and winning would be really scary’,” Affleck told the audience. “And it’s really, really scary…”
Earlier this year, Affleck recalled their decision to bring his mother Chris Boldt and Nancy Carlsson-Page to the 70th Academy Awards.
Speaking to TODAY in the US, he explained: “We were sitting next to our mums and we won, and we kind of hugged our mums.”
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“And I remember how everyone had made such a big thing out of it. As if this was such a novelty.”
He continued: “And I remember thinking, being insecure, like, ‘Why? Why is it weird that we’re bringing our mums?’ Like, ‘Who else do you think we would bring?’ You know what I mean?”
Both men would each go on to earn their own Oscar nominations. Affleck even won Best Picture in 2012 for his film Argo.
In 2021, Damon spoke about how the production of the film was one of the best and most artistically fulfilling experiences of his career.
“Sometimes those moments sneak up on you,” he told GQ. “And that was another one of those moments we never thought was going to arrive.”
“Just, I guess, a mixture of joy and disbelief. And relief. And gratitude. That would probably be it. That was a really nice moment. I’m not ashamed to say it.”
And 25 years later, Damon and Affleck are still teaming up together on films. The 2023 movie Air, which follows the creation of Nike’s best-selling Air Jordan, marks their ninth project together.
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