The road to Best Picture for independent films is usually filled with uncertainty and adversity. Only in hindsight does it seem like some beneficent movie god plotted the course, and that calamities along the way would in retrospect seem like big breaks. Manchester by the Sea might be defined by its rapturous 2016 Sundance premiere, followed hours later by a $10 million Amazon Studios deal that christened its long voyage to the Oscars. But it was an exhausting journey to that point. From the shuffle of director, star and a financier shortly before production, to the incredible sadness of the storyline, Manchester turned its struggles with adversity into good war stories.

“From the moment this movie finally came together, there was a feeling there were people who loved and appreciated certain qualities it had, but that it would never find an audience,” says its star Casey Affleck, who plays Lee Chandler, a man struggling to come to terms with an incident in his past after being forced to return home to bury his brother and figure out his nephew’s custody. “That was true when we were out trying to find the money to make it, through even Sundance, where there was praise for the quality of the movie, but no sense that it was going to be some blockbuster. That has really been one of the best parts of this whole thing; some vindication of good storytelling. From the very first movie I did, people were saying, ‘Small movies are dead. It’s over.’ I remember hearing that conversation on To Die For, and not being sure what it meant. Some 25 years later, they’re still saying that. It’s not true; a story well told can still find an audience, without big stars or big spectacle.”

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Amazon Studios

Producer Matt Damon spent more time on this journey than anyone, and it has hardened him compared to Affleck’s optimism. “Oh, it’s much harder than it is was back when we did Good Will Hunting together,” he admits. “What made that difficult was that Ben Affleck and I were attached to it, and that was what was dragging it down. That movie would have been made in a minute if we weren’t attached. It cost $19 million with Robin Williams’ salary, so maybe it was $14 million below the line. That number, up to a $50 million budget with people just hanging out and talking, got made all the time [then]. Now, it’s so rare, and I got to see why, with Manchester. We had five producers on this film and needed every single one of them. It took a village, literally, to make this thing and I want movies like this one, or Moonlight, to get attention because it’s going to be the death of movies like this if they stop getting that attention.”

The story of Manchester by the Sea began with a meeting around six years ago, between Damon and Boston pal John Krasinski. Each was trying to move from actor-for-hire to actors who write, direct, produce, and create their own vehicles.

“John knew I wanted to direct and said, ‘I have this idea about this guy, an uncle, and there is this town he couldn’t go back to after he moved away to the big city where he was living anonymously,’” Damon recalls. “There was this relationship he had with his big brother, and then there was his nephew and the death of a child, one child, in his past. I loved the idea of this broken man.”

Damon was the second person to hear the idea. Krasinski first proposed it to Girl on the Train star Emily Blunt, shortly after they began dating, when she was shooting The Adjustment Bureau with Damon. “Believe it or not, I was sitting next to Emily on a train when I had the idea,” Krasinski says. “She thought it was moving and beautiful.”

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Michael Buckner

The pitch, Krasinski says, didn’t base Lee Chandler on an actual tragic figure, but came from his own happy experiences in a tight-knit Boston family, and his connection to his nieces and nephews. It sparked the idea “that you are responsible for your family whether you like them or not, and your community as well. It’s almost like a duty. I thought, what would it be like if someone who thought he was a failure for a different reason was asked to try again; to get a second chance on life, one he didn’t think he deserved? It was more that existential second chance question than anything. Could you become a better person if someone else saw you that way? I thought the idea of a kid realizing how special his uncle is when his uncle could never see it was fascinating, and I loved the idea of the older brother knowing this was possible.”

Armed with the title and intention to set it in Boston, Krasinski and Damon began writing, but then sparked to the fracking idea of Promised Land. “That started to catch fire and Matt said he wanted to give the other idea to Lonergan,” whom Damon describes as “my favorite writer on the planet”.

They pitched it to the playwright, and director of You Can Count on Me and Margaret, with Damon ready to make his directorial debut, and Krasinski playing the brother who returns to Manchester to bury his older sibling.

Damon and Affleck both had a great experience starring in a London revival of Lonergan’s This is Our Youth in 2002. Less fun was Damon and Lonergan’s experience on Margaret, the Fox Searchlight film that stranded in dry dock for six years. Lonergan was at the time in a long lawsuit with financier Gary Gilbert, who demanded a shorter cut the director refused to provide. The ordeal left Lonergan wary of straying again from the stage, where his words are treated as sacrosanct.

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Michael Buckner

For Damon, Manchester by the Sea became an opportunity to prove his point in a running debate with Lonergan: that moviemaking could actually be a pleasurable experience. “For 15 years I’ve been telling him that making movies is fun, and he was convinced I was insane,” Damon says. “I’d say, ‘I wouldn’t have spent the last 20 years doing this if it wasn’t the greatest job, ever,’ and he keeps going, ‘You’re out of your mind.’ I got an opportunity here to prove it to him. This was one of those times where, once the script came in and I looked at it and felt it was so good and so much his voice, I just said, ‘Kenny, you have to direct this movie. I’ll play the role and I’ll get the funding. We’ll go make this and no one will bother us. I’m going to prove to you that movies are really, really fun.’”

This was no small gesture for Damon. While his production partner Ben Affleck used a leading man lull to carve a second vocation as a writer/director that eclipsed everything else, Damon was frequently sidetracked by movie-starring jobs that he couldn’t refuse. It prompted him to hand Promised Land to Gus Van Sant, and more recently Father Daughter Time to Gavin O’Connor.

While some might wonder if Damon found Manchester’s complex emotional storytelling too daunting for his first film, that wasn’t the case, he insists. “It was exactly what I was looking for. Spielberg told me this 15 years ago. He said, ‘The first movie you make, just take a small story and see if you have the ability, visually, to tell it. Don’t bite off more than you can chew.’ Manchester was designed for that, and the script came in perfect. But I really felt like Kenny was so locked in at that point. And Ridley Scott and I wanted to do The Martian.”

But Lonergan wasn’t easily convinced to take the reins. What he sparked to in the pitch was “the idea of someone who’s lost that much, trying that hard to do the right thing for what remained of his family. I was attracted to the idea of trying to tell a story like that without sentimentalizing it or having everything turn out okay in the end.”

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Amazon Studios

Lonergan says it takes him three years to turn out a script that’s any good, and this one took longer because he was busy with plays and a Howards End miniseries, plus the Margaret litigation. “I also had a lot of trouble with the first draft, and only felt like I was off and running when I introduced a flashback structure. Writing chronologically was pretty flat.”

After eight months, “I just stumbled on the flashbacks by throwing out everything I didn’t like,” Lonergan recalls. “There’s this janitor, and he’s very strange and you don’t know why. I started over with the first scene that I was interested in: him, shoveling snow outside of the apartment complex. In the first draft, I just had him get up on the day of the accident and go through his day, and it seemed very pedestrian plotting, a series of disasters that seemed pretty uninteresting.”

Lonergan admits that writing this for a friend to direct allowed him to be looser than when he writes for himself, but not in the fully-disconnected way that assignment writers take on, where there is a hesitancy to expend total authorship when the likelihood is your words will be changed by the next rewriting scribe. Way before he agreed to direct, Lonergan put himself on the line creatively because it was for Damon.

“Matt is such a good guy, and I trust him,” Lonergan says. “I knew Matt would never fire me or rewrite the script without my permission. I wrote it knowing I wasn’t going to direct it, that it was going to be his movie, but because I knew it would be made more or less unadulterated, that gave me the liberty to really put my heart and soul into it.”

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Amazon Studios

Lonergan made the tragedy worse than the one in Krasinski’s imagination, and both Krasinski and Damon were amazed by Lonergan’s use of humor in the script, using the logistical practicalities of burying the brother’s body in winter to create revelatory moments for all the characters (think Lucas Hedges’ freezer-induced anxiety meltdown over the realization his dead father was on ice until spring, or Michelle Williams’ character’s chance encounter with her ex, on the streets of Manchester).

“I was blown away,” Krasinski recalls. “His was a much grittier take; a deeper, darker look into what the situation would be like. And that’s absolutely what the movie needed. What was also clear was that Kenny’s writing was so unbelievably specific to him. He’s one of those people who, five minutes into a movie, you know it’s a Kenny Lonergan film. I felt that here. I was disturbed by a lot of the script; how he peeled back layers of things I would have left as, ‘We can all imagine what the impact of that would be.’ He really showed it to you.”

That bleak subject matter would make the film a difficult sell to financiers, and it got more complicated when Damon realized he would have to push the film back at least two years if he was going to direct it.

Lonergan eventually succumbed to Damon’s urging him to direct. By then, Krasinski had his own scheduling problems that prompted him to exit the lead role of Lee Chandler. Damon took on the role, but he too had to vacate because of starring commitments. Damon says: “When I was playing the main role, we had set it up at Odd Lot and Gigi Pritzker. She said, ‘I love the movie, but I don’t know Kenny.’ Fair enough. Chris Moore and I set up this plan where I would have final cut, and while my intent was to help Kenny see through his vision, it worked. We were going into production, but I had this hard start date in Hungary for The Martian, and there was less and less time. I remember speaking to Chris when we were five weeks from principal photography and still in L.A., with no production offices open in Massachusetts. I said, ‘Dude, now we’re putting Kenny in a bad spot.’ I didn’t have another opening in my schedule for two years, and we would have to punt. But Kenny was so ready to go that he had his bags packed. He had Casey reading every draft for support anyway, and on some parallel track, I think we all felt, when I was going to direct it and John fell out, that I’d do it with Casey.”

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Amazon Studios

Affleck says he wished this had been conveyed more clearly to him early on. He remembers exactly where he was when he read Lonergan’s script, meant for Damon and Krasinski. “He wanted feedback from a friend,” Affleck said. “I read it in Atlanta on a Saturday morning and thought, well, so this is what it feels like to read a great script for a movie that will be great.’ I told him how I felt and didn’t think about it again.”

He adds: “Matt will make a great director someday; I remember when I was way, way younger, sitting with Matt and watching Rain Man on laserdisc. He kept winding back this scene, over and over again, where Tom Cruise is looking out a window and the camera is slowly pushing out, and out, as he’s having the conversation with his brother’s doctor. Matt was fascinated by the director’s choices, and that had to be a full 20 years ago. But he’s been so busy acting. I was sure reading it that Matt would make it a great movie, but on the other hand, I think there is nobody who could have directed it as well as Kenny eventually would.”

Affleck read subsequent drafts for his pal Lonergan, and then had no problem committing. The question became, according to Damon, “Can we set this up with Casey?” Odd Lot, understandably flustered by the fast-shifting elements, dropped out. “We were told by WME it was unlikely we’d be able to set it back up quickly,” Damon remembers. “They gave us an exact number we could get for a package with Casey in the lead, at that moment in his career. And it wasn’t enough. So we took all these meetings around town. And we got the exact offers they predicted we would. That’s when Kimberly Steward came into the picture.”

The daughter of World Wide Technology founder David Steward, she just launched her financier/production company K Period Media, with no substantial narrative movie credits to speak of. “She was starting a company to do movies with auteur directors,” Damon says. “She told us, ‘I totally get this.’ She was familiar with Kenny’s work, told us the company she was going to build. We just looked at her and said, ‘Well, do you want to jump to the front of the line?’ And she said she would make it for $8.8 million; a lot more than anyone else was offering. It was exactly what we needed. I think we had $11 million when I was going to do it and we knew this would be right. This movie would never, ever, ever have come into existence without Kimberly.”

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Amazon Studios

Rather than seeing Affleck as a liability, Steward took the leap because she loved his indie work. Surprisingly, the performances of his that stood out most to her were The Assassination of Jesse James by the Coward Robert Ford and The Killer Inside Me. Both lost money. “[Jesse James] is one of my favorite films,” she says. “There, and in The Killer Inside Me, he brings such authenticity to his characters; such subtlety. He communicates such powerful emotions by taking the route less traveled and doesn’t require many words. He was just somebody I wanted to work with.”

Steward, now only the second African-American woman to be Oscar nominated for Best Picture, might have seemed to be making the kind of longshot bet many monied first-timers do, but what she saw in Affleck is exactly what helped elevate the film with his Oscar-nominated performance.

She also got an invaluable tutorial on producing prestige movies from Lonergan, Damon, Moore, and Kevin Walsh, she says. “I did my due diligence on everyone, and even when I bumped up against a few [Margaret] stories, for me [the opportunity] was so clear,” Steward recalls. “I was not going to tell Kenny Lonergan how to make his film and I wasn’t going to tell him what creative elements he needed. I feel very blessed to have come from a situation where I can actually invest in these films, but it doesn’t give me the right to tell the other leader involved what he should or shouldn’t do. I wanted to be there, in service of my director.”

Having Damon in final cut position was also helpful; a concession that was more a relief than a burden for Lonergan. “Matt had been really involved and helpful in the struggle over Margaret, and since he was staying on as producer of Manchester, we discussed different scenarios whereby I and the financier would feel protected. I wouldn’t have directed it if I didn’t have complete trust in Matt having final creative control because, unless something really went wrong, I knew he would cede creative control to me. And if something had gone really wrong I wouldn’t expect to retain creative control. So there was no conflict at all in that arrangement. In fact, it was a perfect solution.”

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Amazon Studios

The other factor that gave Lonergan confidence despite a crunched shooting schedule was all the time he and Affleck had spent discussing the main character. “I would describe what he brought as a really full emotional life, every moment, without having dialogue to express it,” Lonergan says. “His character’s often described as being cut off or emotionally dead, but I don’t see it that way at all. What’s remarkable about Casey’s performance is that he’s very emotional and actively struggling to keep his emotions at bay, from the moment he wakes up until he passes out at night. That, I think, is what make it so compelling to watch him. He’s got his own plan of how he’s going to get through the day in terms of how he interacts with other people, which is not normal. You see him in these pedestrian situations, like when a tenant offers him a tip and he doesn’t understand because he’s trying so hard to control his interactions. You’re constantly wondering what’s going on with him, because he’s so active internally. These are specific choices, not random. We worked hard on this. It’s one of the most consistent and interesting internal thought processes I’ve ever seen in a performance, and if you watched the movie with either of us, we could probably tell you exactly what’s happening with him even when he has nothing to say.”

The uphill part of Manchester by the Sea ended with a rapturous reaction to the Sundance premiere, and Steward recouping her risk when Amazon Studios paid $10 million, winning the film over bidders that included Sony, Universal, Fox and Lionsgate.

Krasinski, ironically, was at Sundance to promote the movie he did instead, The Hollars, which he directed and starred in. “I would be meeting people for my movie and they would be like, ‘Did you hear about the sale of Manchester by the Sea? Did you see the movie?’ I was finding out about it in real time, feeling this swell of pride, because they pulled it off.”

Krasinski resisted the urge to inject his own role into those conversations even though it was his original idea. “Emily makes fun of me and how I’m overly pragmatic, but certain things just make sense to me, and I try not to get emotional about it,” Krasinski says. “Instead of wondering whether I let the role of a lifetime go by, I immediately say to myself, ‘Thank God Casey did it,’ because I wouldn’t have been able to plan any of those nuances and those specific choices he made. They were so perfect and so him. He’s one of the best actors we have, period, and this showcases him in a way nobody has seen before.

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Amazon Studios

“I think Matt would say the same thing here, but there’s no way Matt would have directed this movie like that, and no way I play that part like Casey did. It’s like jazz; you had the right people at the right time and it can’t be duplicated.”

Damon is equally at peace serving as the film’s backbone—and chief spokesman in TV ads—and not director, star or writer, despite Oscar nominations for all three of those categories. He hasn’t exactly gotten Lonergan to admit, though, to an enjoyable experience. “I’m all over him about that,” laughs Damon. “And considering he’s got a tuxedo on now every time I see him, something has worked out. Honestly, that day at Sundance, to see that embrace by the audience…it was so clear, right away, and so palpable how moved everyone was. It was clear to me then we were going to be OK, and then that night Amazon swooped in and gave us that great deal and we’ve never looked back.”

When Affleck took to the stage at the DGA Awards earlier this month to fete his director for Manchester, he joked that Lonergan was “the greatest director who really hates directing.” The reluctant writer/director admits now, “After it’s all over, it’s fun if people like the movie. I’m not suggesting I’m suffering or struggling, but I am still waiting for the actual process itself to be a little more fun.”

Damon, Lonergan concedes, enjoys himself on movie sets, “but he’s a huge movie star and I’m not sure he has the best perspective on this issue. He is not working 16 hours a day in a little room in Gloucester, waiting for them to move the furniture from one room to the other because they forgot which room we were shooting in that day. We had a really good crew but there are screw-ups with every movie, little problems that come up all over the place. I still think it’s probably more fun to be Matt Damon, shooting a multi-million dollar movie, than it is to be Kenny Lonergan in a basement in Gloucester.”