The rival who became Matt Damon’s first Hollywood nemesis: “He’s a very savvy businessman”

Everyone knows that Matt Damon and Ben Affleck leaned on each other while trying to make a name for themselves in Hollywood, with the Bostonian best friends living together, sharing a bank account, and trying to drag each other up by the collar until Good Will Hunting launched them into the mainstream.

Their bond has evolved into one of Hollywood’s greatest love stories, and every story needs an antagonist. For Damon, there was one actor who was part of the circle he and Affleck travelled in during the early 1990s who seemed to thwart him at every turn, leaving him to question how they made it as a star before he did.

The cast of Robert Mandel’s 1992 drama School Ties features almost all of them. Damon was the second-billed star behind Brendan Fraser; Affleck played a minor role, with Randall Batinkoff and Anthony Rapp also among the ensemble. The quintet regularly auditioned for the same projects, but the sixth member of their supposedly close-knit group, Chris O’Donnell, had his own agenda.

Scent of a Woman happened right during School Ties,” Damon shared with Vanity Fair in 1997. “The whole cast went down to audition for it. Chris O’Donnell was a business major at Boston College, and he’s a very savvy businessman.” The gang were all excited by the prospect of potentially sharing the screen with Al Pacino, but they were at a disadvantage when O’Donnell refused to share.

“I go up to Chris and I say, ‘Have you heard about this movie?'” Damon continued. “And he says, ‘Yeah’. So I say, ‘Do you have the script?’ ‘Yeah.’ ‘Can I see it?’ ‘No, I kinda need it’. Chris wouldn’t give it to anybody. Later, Ben, me, Randall, Brendan, Anthony Rapp, we’re all commiserating about our auditions, talking about how they didn’t go well. Except for Chris.”

Of course, O’Donnell’s decision not to let his so-called friends read the script worked out very well for him when he was cast opposite Pacino in Scent of a Woman, earned a Golden Globe nomination for ‘Best Supporting Actor’ and was singled out as one of the industry’s brightest new stars.

That eventually led him to his blockbuster debut in Joel Schumacher’s Batman Forever, where he played Robin. With his newfound status, O’Donnell wanted more money to suit up alongside Val Kilmer than he’d initially been offered, which saw Damon brought in to audition as a honeytrap of sorts to convince the director’s number one choice to accept the offer.

Even when Good Will Hunting won him an Academy Award and opened the doors that had previously remained shut, Damon still couldn’t believe O’Donnell’s luck. Whereas he said his average salary across Good Will Hunting, Francis Ford Coppola’s The Rainmaker, and Steven Spielberg’s Saving Private Ryan was “significantly under half a million per picture,” his nemesis was rolling in cash.

“Chris O’Donnell made $10 million last year,” he said incredulously. “Chris… O’Donnell… made… ten… million… dollars… last year,” Damon added for emphasis. Fast forward three decades, though, and it’s fair to say things worked out better for him than they did for his early career rival.

Damon is one of the industry’s biggest, most dependable, and versatile stars and has been for a long time, while O’Donnell hasn’t even been in a movie since 2010. He may have lost the early battles, but he’s easily won the long-term war.

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