Oscars Flashback: Matt Damon and Ben Affleck 1998

In 1998, Matt Damon and Ben Affleck transcended from two aspiring actors and filmmakers to Oscar winners. As one can imagine, they and everybody they had ever known were ecstatic amid the exciting acclaim--so much so that Affleck received a call while in the press room.

Childhood friends from Cambridge, Mass., Damon and Affleck went on the ultimate journey together after writing Good Will Hunting and watching it come to fruition with them co-starring alongside Robin Williams.


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The film not only went on to rake in over $225 million at the box office ($318 million, inflation-adjusted) but also earned them high honors, including a Golden Globe and an Oscar for Best Screenplay.

The two were baffled and truly humbled by the success of their film. They brought their moms along as their dates to the Oscars and had a slew of family members and friends eagerly waiting to potentially watch them win their first Oscar that night.


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While Damon and Affleck are fielding questions from the media about winning the Best Original Screenplay award, Affleck fidgets about, pulls his StarTAC phone (the most technologically advanced phone at the time) out of his pocket, and answers it while Damon continues to answer the question.

After quickly hanging up his phone, Affleck recounts the comical experience of having his mother with him for the Oscars.


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"My mother told me that...she's considering this her grandson and she's holding it for ransom until she gets a real one," the then-25-year-old actor says.

As for the experience as a whole, Damon, who was also nominated for Best Actor, summed it up perfectly when asked which award he wanted to win more.

"Are you kidding me, man? I've never even been here before," he says. "I didn't care."

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