Directing a 'Lesser Known' Ben Affleck and Matt Damon 'Was an Advantage' for 'Good Will Hunting'

Ben Affleck and Matt Damon star in 'Good Will Hunting' (1997).

More than 25 years ago, Ben Affleck and Matt Damon were just a couple of unknown actors that Gus Van Sant had trouble tracking down after reading their script.

The Good Will Hunting director, who earned his first Oscar nomination for the 1997 movie, told me he was almost passed over by Miramax boss Harvey Weinstein, but Affleck and Damon's "lesser known" status brought him back into play.

"Something went wrong with the deal; I kind of was tossed aside, and they continued looking," he recalls. "I probably wanted a final cut or something, which I was getting by then, and so there was a problem there. They kept searching, and a lot of very big directors considered it and got interested in it. But because Matt and Ben were not like Brad Pitt and Leo DiCaprio, directors actually dropped out. They said, 'We're not sure. We just can't tell.'"

Gus continues, "And on my side of things, I always want my characters to be lesser known, so you have a chance to meet somebody new as opposed to a film where you're going to see a particular person play a role. I always want the audience to get lost in the character. So, to me, that was an advantage. So, I was still around by the time they couldn't find anyone else, basically."

Set at MIT, Good Will Hunting follows genius school janitor Will Hunting (Damon), who gets discovered by a professor (Stellan Skarsgard) after solving a graduate-level math problem. Affleck co-starred as Will's streetwise friend Chuckie Sullivan.

In addition to Gus’ Best Director nomination, the movie earned Oscar nods in the Best Picture category and Best Actor for Damon. The film won Best Supporting Actor for Robin Williams, as well as Best Original Screenplay for Damon and Affleck.

Gus Van Sant directs Matt Damon in a scene from 'Good Will Hunting' (1997).

Gus previously worked with Williams in developing an early version of his 2008 movie Milk, a biopic about Harvey Milk. He also met Damon when the young actor auditioned for a role (that ultim ately went to River’s younger brother Joaquin Phoenix) in Gus’ previous film To Die For.

"I really wanted him to play the character that Joaquin played, but we had to admit that he really looked more like a very good-looking jock," recalls Gus of the 1995 camp hit about a small-town weather reporter (Nicole Kidman) who seduces teenager Jimmy (Phoenix) and convinces him to kill her husband (Matt Dillon).

"And it would change the structure of the idea that Nicole Kidman's character was actually just using this helpless kid just to get rid of her husband. And he was not as forlorn as Joaquin," he adds. "We sort of had to face that, which was too bad. And Matt was really trying to go for it, really trying to lose weight and trying to be in that film."

But their paths would cross again shortly after when Damon and Affleck sold their first screenplay, big news for the trades of the time.

"There was a picture of Matt and Ben holding a check that they had gotten from Castle Rock for their script," Van Sant explained. "And it was like a big deal that an actor or a pair of actors had written a script, which is funny because it seems like a lot of actors today, a lot of different people write scripts. But it warranted a photo on the cover of the daily Variety."

Gus ended up reading the script for Good Will Hunting after a Miramax exec sent it his way, and the rest is Hollywood history.

"I immediately called; I tried to find Matt or Ben just to tell him that I liked the script, not that I wanted to direct it," he said, noting that by the time he actually reached them, he was all in. "It was hard to find them."

Good Will Hunting is now available to stream on Max.