MATT DAMON & BEN AFFLECK are now well established as Hollywood Gold, with a rich catalogue of great films and a string of awards to their name. But go back to 1994 when Damon, a jobbing actor, was sleeping on Affleck’s bedroom floor and things couldn’t be more different. When the pair agreed to team up and develop Damon’s 40 page college project into a full length screenplay, nobody could’ve guest they were on the long path to become record breaking Oscar winners.
In an in-depth interview with BOSTON MAGAZINE, they unveil the 4 year process from start to finish, with every set back, every twist and turn, including how a $600,000 deal with Castle Rock turned out to be a real stinker and how attaching the late ROBIN WILLIAMS proved to be the key to it all.
Matt Damon: I was in my fifth year at Harvard, and I had a few electives left. There was this playwriting class and the culmination of it was to write a one-act play, and I just started writing a movie. So I handed the professor at the end of the semester a 40-some-odd-page document, and said, “Look, I might have failed your class, but it is the first act of something longer.”
Anthony Kubiak (Damon’s professor at Harvard): The thing that they always say when you submit a script to an agent is that they read the first page and they read the middle, and they can tell if they want to continue. They can see whether you can capture the human voice and dialogue. And that was all over this work. It was very authentic and real.
Damon: I was gonna be getting out of school in two or three months when I got a part in the movie Geronimo: An American Legend. I went out to Los Angeles and stayed with Ben. I slept on his floor. I brought my Act I of the Good Will Hunting script and gave it to him.
Ben Affleck: Matt said, “Look, will you help me write this? I’m not sure what it is or where to go.” So we started writing it sort of back and forth.
Damon: The only scene that survived from that document—it survived verbatim, actually—is the first time that I meet Robin [Williams].
Chris Moore (producer): We had been working on Glory Daze—that’s how I met Ben. And I always liked Matt, because we’d met in Cambridge. They said they had this script they’d been working on. So I said, “Sure, I’ll read the script.”
Damon: It was the first thing we woke up thinking about and the last thing we thought about before going to bed.
Affleck: We came up with this idea of the brilliant kid and his townie friends, where he was special and the government wanted to get their mitts on him. And it had a very Beverly Hills Cop, Midnight Run sensibility, where the kids from Boston were giving the NSA the slip all the time. We would improvise and drink like six or twelve beers or whatever and record it with a tape recorder. At the time we imagined the professor and the shrink would be Morgan Freeman and De Niro, so we’d do our imitations of Freeman and De Niro. It was kind of hopelessly naive and probably really embarrassing in that respect.
Moore: They wrote a great script, and I read it and was like, “This is one of the best scripts I have ever read, and I would love to produce it.” The three of us agreed we would try to get it made.
The script was completed in 1994, at which point Damon and Affleck approached their agent, who started shopping it around.
Patrick Whitesell (agent): Matt had talked about the script he was writing with Ben. Usually when you get a script from actors you don’t have high expectations.
Damon: I didn’t realize the stereotype at the time was that every actor has a screenplay.
Whitesell: I read it over the weekend and I was blown away. It’s almost an impossible thing to get a movie made that is written by two actors who want to star in it, when no one knows who they are. The only time it happened that I know of was when Sylvester Stallone did it in Rocky.
Damon: Nobody knew us. They knew we’d worked. We had résumés with movies on them. I think Ben had done Dazed and Confused and we’d both done School Ties, so we had these résumés that had some professional work on them.
Whitesell: I went out with it on the weekend to every studio in town and we said, “Here are these guys, and they have to star in it.”
Damon: We never cared about money—we wanted to be in the movie. That was our only thing. That was our big ask.
Whitesell: In Hollywood, there’s a network of creative executives, and when they hear something is good it catches fire. My phone started ringing like crazy. Everyone wanted to sit down with Matt and Ben. It started getting hot. There was a bidding war.
Damon: Patrick Whitesell, in the span of just four days, kind of whipped the town into this frenzy. We sold it to Castle Rock, which was our very first choice. They had a great reputation.
Affleck: I remember it was printed in Daily Variety that we were going to get $600,000 on it. We had no credit, so we went to rent this house that was $3,000 a month, and we used a copy of the Daily Variety to get the place. I was like, “I don’t have credit, but this is who we are.” And the landlord was like, “All right, sure.” We thought $600,000 would take care of us for 20 years, so we rented nicer apartments and each bought Jeep Cherokees. And we were completely broke in a year.
Damon: We started working out because we were like, “We gotta get in shape for the movie”—four years before it got made. I remember just feeling like the film moved at such a glacial pace.
Moore: Rob Reiner at Castle Rock said, “Look, you have two movies in this script, and the movies are fighting each other. There’s the thriller aspect of the kids from Southie thwarting the big government agency, and then there’s this really awesome character story about this math genius and his relationship with this shrink. And we don’t think those two can live together.” And to their credit, Castle Rock said, “You guys wrote a great script and you’re the stars of the movie, so we’re putting it to you. You’ve got to pick one.”
Damon: At first we were terrified because we had this 120-to-130-page script, and once we removed the NSA stuff it was 60 pages. We were going, “What’s the movie then? What happens?”
Affleck: It was a complete overhaul.
Castle Rock liked the new script, which focused on Will Hunting, but disagreements over who would direct the movie almost torpedoed the project.
Affleck: When the question came up, we would say, “We’ll direct it!” and there would be silence in the room. It was a polite silence, like, “Are you high?” But it was the beginning of my own directorial ambition.
Moore: So Castle Rock, in my opinion, did the right thing, and said, “Okay, we have a creative disagreement. Even though we own the script and we could fire you guys, we’ll give you time to go out and find somebody who will buy your version of the movie. But there’s a price tag: We want to get our money back, and if you can’t find anybody to buy it, when it comes back to us, you guys are not the stars.”
Affleck: They told us that someone else would direct it, rewrite it, act in it, and that we’d be lucky to fucking get invited to a premiere. But instead of scaring us, it kind of emboldened us. Because then we really thought, Fuck this. We’re gonna go out there and do it.
Damon: At that point Castle Rock was having us do these rewrites and we were going in circles.
Affleck: We were so frustrated that Castle Rock wasn’t reading the script, so we felt like we had to develop this test. We started writing in screen direction like, “Sean talks to Will and unloads his conscience.” And then: “Will takes a moment and then gives Sean a soulful look and leans in and starts blowing him.”
Damon: They weren’t reading the script closely anymore. It was literally probably a full paragraph about what these two characters were doing to each other.
Affleck: We would turn that in, and they wouldn’t ever mention all those scenes where Sean and Will were jerking each other off.
Damon: Over the following weeks, we went back to meet with all of the studios who had bid on it who we hadn’t gone with, and basically everybody took the meeting just to tell us to go fuck ourselves.
Affleck: We went back to Ted Field at Interscope, who had offered us a million dollars. And then we got in the room with him and he was like, “I’ll tell you why I took this meeting: Because I’m going to tell you I’m going to pass.” I actually used that as inspiration for a scene in Argo. That’s when the dryness started to take hold in the back of the throat. Like we might be cooked.
Damon: Ben gave it to [Chasing Amy director] Kevin Smith and said, “Will you please save us? Will you direct this movie?” And Kevin read the script and was unbelievably kind. I still remember the message. He said, “I wouldn’t dare direct this movie, this is so beautiful.” Kevin went in personally to Harvey Weinstein’s office at Miramax and handed him the script, and basically said, “Drop everything you’re doing right now and read this.”
Affleck: Kevin said, “I read it on the toilet, and I stayed on the toilet the whole time because I was so into the script.” We had a lead that Harvey might do it from Kevin, and then we just attacked. And he said yes, and it really felt like a miracle.
Damon: I still remember the phone call with Harvey. He had two notes on the script that were excellent, both very minor things. In one of his notes, he said, “I don’t like the chess thing”—there was a thing where Will played chess—“take that out.” And he goes, “And the blow jobs gotta come out, guys.” And we were like, “Okay, we found a home.”
Weinstein ended up buying the movie from Castle Rock for more than $1 million in 1995. Damon and Affleck started to meet with a new batch of potential directors, including Gus Van Sant.
Affleck: We met with Mel Gibson, and Braveheart had just come out, and was as hot as could be. But we hadn’t seen Braveheart and Harvey was like, “YOU HAVEN’T SEEN BRAVEHEART? FUCKING LIE TO HIM AND TELL HIM YOU LOVE BRAVEHEART.” So the first thing we said was, “We just want to tell you how much we loved Braveheart!”
Moore: Mel Gibson developed it for a few months. Matt at one point said directly to Gibson, “Look, man. We’re getting too old. If this keeps going by, Ben and I can’t play these parts. Is there any chance you’d just let it go?” And to Mel’s credit, he said, “I totally understand what you’re saying.” That was a real stand-up thing to do.
Gus Van Sant (director): I was in New York, and Miramax sent the script to the hotel. Usually when I read a script, after a few pages, I put it down—but this kept me going.
Moore: Gus was not as established as he is now, and so Harvey wasn’t jumping on the Gus bandwagon. It wasn’t because he didn’t believe that Gus could make a great movie, it’s just Harvey is a marketer and knew Mel Gibson is a lot different than having, you know, Gus Van Sant.
Van Sant: I got in touch with Ben Affleck because I knew [Ben’s brother] Casey—we did To Die For. Ben and I had a meeting at Denny’s on Sunset here in L.A.
Affleck: Denny’s was sort of normal for us. Where else would we go? We didn’t even have any frame of reference of what famous people were supposed to do.
Damon: At that point we moved back to Boston. But for a year, the movie didn’t get made because Gus and Harvey fell out over final cut. So we’re living in Davis Square, Gus Van Sant wants to do our movie, but we can’t do it. We’re pretty crestfallen at that point. Then Harvey put Lawrence Bender on the movie as a producer.
Van Sant: So Lawrence Bender became the super producer and all of a sudden I was just on it. Lawrence said, “Okay, you’re doing it.” And I was doing it. But the moment where Harvey really wanted to get the movie done was partly due to Matt being cast in John Grisham’s The Rainmaker, by Francis Ford Coppola.
Whitesell: That was the period of time when Grisham was the biggest thing in Hollywood. It validated the fact that Matt was a leading man.
Damon: I sent Harvey a fax that literally said, “Dear Harvey, I am the Rainmaker.” He called me and he was like, “What does that mean?” He thought I was getting a lawyer or something. I was like, “No man, I got the Coppola movie, they cast me as the lead.” And Harvey goes, “THE GRISHAM MOVIE? THOSE THINGS MAKE $100 MILLION!”
Affleck: Matt told you the story about “I am the Rainmaker”? I can’t believe Matt would tell that story about himself. That is what happened, but Harvey didn’t then green-light the movie. I think he was buoyed by it, but Robin [Williams] really was the rainmaker.
Damon: Robin had just done Jack with Francis Ford Coppola. When he read the script and really liked it, his one question for Coppola was, “Who are these guys?”
Robin Williams (Sean Maguire): That used to be the joke, “I want to see some ID.” I read it and went, “This is really extraordinary.” The Sean character had such history that I was going, “Where did it come from?” I found out later that it’s based on Matt’s mother and Ben’s father, kind of a synthesis of the two.
Moore: Robin signing on definitely was the linchpin for the movie getting made.
After landing Robin Williams, the team spent a hectic few months in early 1997 scouting locations in Toronto and casting actors in New York. They rounded out their Southie foursome with Ben’s younger brother, Casey Affleck, and the actor Cole Hauser. While in Toronto, however, they realized that they would need to shoot some scenes in Boston to capture the city’s character.
Moore: The biggest role that we spent a lot of time casting was the Skylar role.
Lawrence Bender (producer): We were casting in New York, auditioning all these girls. And in walks Minnie Driver.
Van Sant: It was early in the morning and we were in the Bowery Hotel, and for whatever reason we had stayed up really late, so we were in a vulnerable state. And she was really good. I mean she is a really great actress, so she just blew us away.
Bender: The other really hard role was the one that Stellan Skarsgard played, Gerry Lambeau. It was such a pivotal role, and we just couldn’t find the right person.
Stellan Skarsgard (Gerald Lambeau): I was in Rhode Island shooting Amistad with Spielberg, and I was sent the script. I didn’t consider turning it down, ever. I had to go to Boston and see the boys and Gus. We went out to some bars in South Boston. The driver was so afraid that his black car would be destroyed there. It was pretty dangerous back then.
Damon: And then one night we took Robin to the L Street Tavern….
Affleck: Robin wanted to get a taste of Boston. I remember thinking, This is a fucking mistake. I mean, you gotta remember Whitey Bulger was still around and running things. And then it just turns into a mob scene. Guys got really drunk and wanted to fight me because I had my hat on backwards.
Williams: I remember this guy came up with a heavy Irish accent, I couldn’t understand a word he was saying, and another guy, a Southie guy, said, “He wants to know where your private plane is.”
Charlie Harrington (Boston location scout): The whole neighborhood found out about it, and we kind of got mobbed and left. I remember Matt and Ben looking at it and thinking, I wonder if this will ever happen to me?
Damon: When Robin got a feel for that place, he called Harvey and was like, “We have to shoot this bar,” even though he wasn’t in any of those scenes. So then we got a message from Harvey and he was like, “DON’T TAKE ROBIN TO ANY MORE LOCATIONS!” It was because of Robin that we got to shoot at the L Street.
Shooting started on April 14, 1997, and was completed in just nine weeks.
Missy Stewart (production designer): We would talk about what would make it more “Boston.”
Moore: We had this costume designer, Beatrix, who came from Eastern Europe. The wardrobe she picked for the first day for the four guys so freaked us out that we had this mini meltdown. They were working class, but she dressed them almost like homeless people. Casey and Ben were trying to convince her, Look, these guys are poor, but the way they show their thing is they buy name-brand shit. They wear the Nike sweatsuit or the Adidas sweatsuit. In one of those panicked producer calls, I called Reebok and was like, “Look, I need some sweatpants.” It was five in the morning because we were trying to get a shot when the sun came up and this lady from Reebok got out of bed, showed up, brought all the stuff. Then there were the marketing people, who were hoping we would use chain restaurants so that maybe they could get a marketing tie-in. Matt and Ben kept saying, “No. We gotta go to Kelly’s Roast Beef. We gotta eat at the Tasty.”
Bender: I’ll never forget the first day of shooting. After it, Matt and Ben and Gus went in for this big hug. This was their baby, more than anyone else.
Damon: The very first day, I remember we started crying, because it was a scene between Robin and Stellan. And when Gus called action and we watched these guys—I mean accomplished actors—do our scene verbatim, we had waited so long for this to happen. I remember just sitting next to Ben and I had tears rolling down my cheeks because I was just so happy and relieved that it was really happening.
Affleck: We did tear up a little bit. But why is Matt saying this shit? Like, he holds his fucking tongue for 15 years and now because it’s Boston magazine, he says he started crying? His career is not over, you know what I mean? He needs people to believe that he’s like Jason Bourne or whatever!
The movie was centered on the relationship between Will Hunting, played by Damon, and therapist Sean Maguire, Robin Williams’s character.
Van Sant: The main scene for me in the movie is the first time Will meets Sean, that was always kind of the best scene. And it was also the original scene that Matt wrote. Sean was a sad character, and Will discovers that he has this Achilles’ heel.
Williams: It was reacting to him and listening to him, as a therapist and also a therapist who has a history, and him kind of pushing my buttons and me trying to stop him from doing that and literally going, “I know what you’re doing here.” And finally he pushes the wrong button and the next thing, Sean just snaps.
Su Armstrong (executive producer): I think the scene that comes back to me a lot—it was such a surprise when we were shooting—is when Will attacks Sean about his wife and Sean just slams him against the wall and basically says, “Don’t you talk about something you don’t know.” I was so shocked the set didn’t fall down, because it was so violent.
Williams: You know that line, “I’ll end you”? Matt or Ben said that they were in a bar when they saw this big guy picking on this little guy and saying, “Hey, I’ll kick your ass,” and all of a sudden the little guy got right in his face and said, “I will fucking end you.”
Moore: When Robin and Matt were shooting the scene on the bench in the Public Garden, in the movie it seems like they’re the only people in the park. And Robin at this time is a massive star. The Boston police deserve a lot of credit for helping us with this because it was not part of our deal with them. We ended up at one point with over 3,000 people out there, watching that scene.
Williams: While shooting the scene that day, I would ask Gus what to do, and he would say, “Just keep talking to him, just keep listening to him.” It was intimate, simple. I’m sitting down with him in this beautiful place in the Public Garden, and it was kind of this surreal thing with these swan boats.
Damon: Robin’s best addition is the last line of the film. There was nothing scripted there. He opens the mailbox and reads the note that I had written him. Gus and I were right next to the camera, because every time he came out for a new take I would read the letter to him because it’s a voiceover. He came out saying different lines every single time. When he said, “Son of a bitch stole my line,” I grabbed Gus. It was like a bolt, it was just one of those holy-shit moments where, like, that’s it.
The most famous scene in the movie involves Will coming to the defense of his best friend, Chuckie, who’s being taunted by a cocky Harvard graduate student at a Cambridge bar. After Will dresses down the grad student, he wins over Skylar.
Affleck: Shooting in Harvard Square was a big deal for me. It’s a quarter-mile from our high school, Rindge & Latin—and we’d go there after school, and out there to drink when we got older. It was sort of the nexus of our social life in a lot of ways. So getting to bring the circus home was a really fun thing.
Chris Moore: The Harvard bar scene has got so much going on. He has to meet the girl, we have to learn he hates smart people, that these guys are townies, and that his boys have his back. Then it wraps up with the famous “How do you like them apples?” It is, entertainment-wise, one of my favorite scenes.
Scott William Winters (the Harvard grad student): We didn’t do a lot of takes. I think Gus liked what I was doing. And Matt and Ben were really complimentary. Matt was like, “You know, dude, if you can find a way that gets you out of the room that’s more dignified….” I really appreciated it, but I told them I thought that the way it was written was spot-on.
Affleck: “How do you like them apples?” is a saying people said all the time—at least when we grew up. All we did was affix that joke to our story where a guy basically trumps another guy over a girl, a sort of Rocky, underdog, working-class hero over this smug, Ivy villain, which was a little bit cartoonish, but we thought maybe we could get away with it.
As both a working stiff and an intellectual, Will Hunting embodied Boston’s dueling identities.
Will is encouraged by MIT professor Gerald Lambeau to pursue a career in math, but he hedges, unwilling to leave his friends in Southie behind—until Chuckie tells him, “You got something none of us have” and would be a fool not to take the opportunity. “You don’t owe it to yourself,” Chuckie says. “You owe it to me.” It was a scene that they had practiced hundreds of times in their living room.
Affleck: Matt and I worked construction a couple of summers for a guy named Paul Maggiore. That, to me, felt like those moments where I was taking real-life things and putting them in the movie. Things that mattered to me.
Damon: I remember vividly the scene where Ben tells me to leave town, where he says,“If you’re still here to come over and watch the Patriots game, I’ll fucking kill you.” That scene, we did three takes on Ben. He got it in the first take and I knew we were done, we could go home. And he had this kind of stunned look on his face and Gus was like, “Would you like to do another?” And Ben was like, “Yeah, yeah,” so he did another one, which was great. And Gus said again, “Would you like to do another one?” This has taken 15 minutes, at the most, for Ben to do these three takes. I was like, “Honestly, you got it on the first one.” And he knew it, but he couldn’t believe that it was over.
Affleck: It was like a lot of things, where the buildup is bigger than the event itself, and the event is over pretty quickly.
Damon: He had been waiting to do this for so long. And he’d done everything he wanted to do with it. It was simple, it was honest, it was beautiful. But there was still the shock of, he can’t be done, you know?
Affleck: I had been thinking about the scene and how it was gonna play out, and then reading it out loud, and writing it, and rewriting it, and rehearsing it in my mind over years and years. It was just kinda like, “Is it over?” It’s just hard to almost internalize the fact that, okay, we’re going to wait four years, and it’s gonna be over in five seconds. Kind of like losing my virginity.
The movie had a limited opening in December 1997—just beating the end-of-year deadline for the 1998 Academy Awards—but opened across the country in January 1998. Its nine Academy Award nominations included best screenplay, best supporting actor, and best picture.
Missy Stewart: It was an amazing lineup that year, with Titanic and L.A. Confidential.
Damon: Ben and I talked about it recently. We were younger than we felt. I was 22 and Ben was 20 when we first started writing it. And then it came out when I was 27 and Ben was 25. I mean, Ben’s still the youngest writer to ever win an Oscar for screenwriting. I’d be the youngest if it weren’t for Ben. Fucking asshole.
Stewart: It was just a wild ride. We were all really happy when Matt and Ben won the screenplay award, then Robin won for best supporting actor, and that we were up for the best picture category.
Su Armstrong : We would have taken home a few more awards if not for that boat picture.
Affleck: The thing about the Oscars is that I sort of affirmed that image that people had of me as a complete idiot, because I just kind of panicked. I mean, we thanked Boston twice. Don’t you think Boston was glad to see it thanked the first time?
The movie launched the careers of both Damon and Affleck. Fifteen years later, its legacy follows the careers of the cast and production team everywhere.
Skarsgard: It’s amazing how often people come up to you in airports and on streets and start talking about it and say, “I see it at least once a year,” or “I’ve seen it 30 times.” It’s a film that people carry around with them in a way.
Williams: I think it’s a movie that people experienced. It’s more than a movie for some people, which is kind of wonderful.
Affleck: When I look at my own career, my life, and particularly directing, it’s all rooted in this experience. Realizing that the actors need to take responsibility for their performances, and that there is no right answer and that it’s just about discovering things. All that came from Gus.
Damon: I don’t think there could ever be another movie that I felt that way about. Because of what it meant for our lives, because of that time in our life. Another movie couldn’t occupy that much of my heart and soul at this point in my life. A movie could never change my life like that again.
Affleck: For a while, we thought maybe we should chill and just do other stuff, and not be Matt and Ben, Matt and Ben. But now, I’m gonna direct Matt in the Whitey movie. We have our company together, we’re developing together. And Matt lives down the street from me like he used to. His kids are living with him, the way we used to live with our folks. The only difference is that we have pools.