He’s gone to the jungles of the Amazon in The Lost of City of Z and explored the depths of the solar system in Ad Astra, but at his core, James Gray will forever remain a tried-and-true New York filmmaker. Even though he’s been an LA resident for quite some time, the bones of the Big Apple nestle murkily inside the frames of the director’s oeuvre, crackling with his tender mixture of ’70s New Hollywood grit and Golden Age romanticism. “James Gray and New York is a combo that simply never misses,” Rory writes in a four-star Letterboxd review of Gray’s emotionally fraught 1920s period piece The Immigrant.

The Criterion Channel surely agrees, as they’re currently streaming a collection titled James Gray’s New York, which showcases his first five features: from 1994’s Brighton Beach-set Little Odessa through to the Ellis Island views of 2013’s The Immigrant. “Criterion having this James Gray New York collection is incredible. Every movie better than the last, and this is an absolute masterpiece,” is how mllaurino describes their five-star experience with 2008’s aching romance Two Lovers, while Sumner finds the Gray touch present from the very start of his career, saying of Little Odessa that “Even in his debut feature, James Gray’s New York has a romanticism and cultural specificity that belies his age at the time.”

As Letterboxd continue to make their way through the collection and drop their praise, I sat down with the director for a lengthy conversation about these five features, breaking down specific sequences like We Own the Night’s riveting car chase and The Immigrant’s transcendent final shot, along with the rich melancholic themes that inspire folks like Lee to declare, “James Gray is one of the greatest living filmmakers.”

You’ve mentioned that The Yards is the film you learned the most on, from working with different generations of actors like James Caan compared with Mark Wahlberg to collaborating with Harris Savides on the cinematography to dealing with the studio system. When you think about that movie now and lessons learned, what stands out the most for you?
Great question. It is true; I learned more from that movie than any other, and it’s my biggest failure. The biggest thing I learned actually is a creative thing, which is the essential importance of point of view. I don’t mean thematic point of view; the movie always had that. It had a unity of point of view in that respect, but the original idea for the movie was that you were going to follow each one of those characters: Mark’s character for the first third or the first quarter, and then the narrative changed hands to Joaquin [Phoenix]’s character, and then it changed hands to James Caan’s character, and it ended up with Charlize [Theron]’s character, but it didn’t work. It didn’t work at all. The movie didn’t function. You realized it didn’t function because there was no unity of point of view.

I , from a narrative standpoint, realizing that there was a certain degree of rigor and structure that was required of you to tell a story elegantly on-screen with emotion. There might be some people who would find what I just said terrible, because I know there’s a whole cinephile culture that is not as obsessed with narrative rigor as I am. Some actually embrace a looseness and oddity, which is great for them, but I don’t think that stands up very well over time. It’s not my taste anyway, so my attitude is to try and get the narrative thing right.

There’s an infamous story from We Own the Night of Joaquin needling Robert Duvall, mocking him and getting an earring for his character just to mess with Duvall to draw out a reaction in their scenes together. You have a similar way of working with actors, using techniques off-screen to give one person a bit of direction that is designed to incite a reaction.
That’s true. Joaquin and I always felt that we had to go 152 percent into whatever we were doing. Sometimes, I think we probably went too far. There were things that I would not do today. All that stuff—there is no art without risk, and you need to sometimes do things that are on the edge. Which is why I think the whole idea for artists—for artists now, I’m going to be specific—of safe spaces and intimacy coordinators and all this stuff, is actually quite anti-artist because it’s the corporation dictating to us that a lack of risk is what’s important to the corporation. Our job is to take those risks, and that leads sometimes to unpleasant things, difficult things, scary things.

Joaquin would constantly ask me, “Have [the other actor] hit me in the face,” or pour charcoal into his mouth, which he actually does on-screen. The set was sexually charged and violent. We try to have the set feel like that. It’s probably an uncomfortable and unpleasant thing to say, but fuck it. I think it shows up in the movie, and in a great way. Obviously, this is very much the kind of tradition of [Elia] Kazan, and I used to sit in on [acting coach] Stella Adler’s classes and she would get very violent with the actor. You have to expose yourself and be vulnerable, and that tradition is gone. In some ways, for the good—it’s not necessary to traumatize people that way—but in some ways, it shows up in the work. It feels too safe.

Because you mentioned that sometimes you feel like you maybe went a little bit too far, is there an example that comes to mind of something that maybe nowadays you wouldn’t have done?
We shot a car chase [in We Own the Night] with a level of control that I think is probably not acceptable. There’s a shot in the movie in which there was almost a head-on collision, which would’ve killed everybody in the car. The shot is actually in the movie, up to the frame where the camera got smashed off the side. I don’t want to say that we didn’t take all the proper precautions, because at the time, I guess we did, but there was a level of risk shooting that sequence. A car that goes under a truck, I . It was a very risky thing to do. It’s that level of charged atmosphere. Joaquin drinking charcoal, I mean, I just don’t think that’s necessary. I think he could have drunk black coloring... You know what I mean? It’s that kind of thing.

But maybe the reason you feel that way is partly because of what it is I’m talking about, where both Joaquin and Eva [Mendes] actually act it brilliantly. It’s an underrated aspect to any sequence like that. What she’s doing is great in a state of utter panic, and his expressions are perfect. I mean, you have to realize how that was shot. You have the stuff I’m talking about—the dangerous stuff, which Joaquin and Eva thankfully were not involved with. But for them, it would be like a shot of Joaquin where his eyes would bulge or whatever, or her in the backseat screaming—that’s done in a car that’s not moving where you’re just shaking it around and they have to act it.

So there’s some of that, but also I think it’s about the subjectivity of it. This comes back to this whole point of view question about The Yards. It’s a very subjective scene. There’s very little outside the car. It’s almost all from inside their point of view looking out the window and very simultaneously claustrophobic, but also about two cars on the road in the rain. Although it’s primarily interior, even, so maybe that’s what it is. I don’t know. I can’t speak to that exactly, but maybe that’s what it is.

The other moment I want to mention from We Own the Night is the shoot-out in the long reeds, where Mark Wahlberg’s character hits the ground the moment that the shooting happens and is paralyzed by this PTSD he has from being shot earlier in the film. I love that choice, because it emphasizes this idea that sometimes you’re not able to live the life you planned for yourself, which we see in Joaquin’s character as well.
That’s a major thematic idea in the movie. You can have as much agency—if we use that silly word—as you want. It doesn’t matter, because the forces outside of your own self are much greater and often dictate your path in a way that is not what you want. So that was part of what was trying to be expressed there.

In the Mark Wahlberg case, I had read about, obviously, someone like Frank Serpico who was also shot in the face, and what happened to him. He just moved to Switzerland and disconnected. This idea that you can get shot and go right back into the theater is really wrongheaded. You’re going to have some problems. I was trying to make it about some form of PTSD—not that it was a deficiency in his character, but he had been traumatized by this moment and nobody had let him recover. That’s really what it’s about. Nobody wants to hear it, letting him be himself.

In the case of Joaquin’s character, the world had other plans for him than he had for himself. But that goes back to my own taste for art and literature, which is that we have our destinies.

Heartbreak deserves its own moment to shine in the movies, because heartbreak is one of life’s great truths and one of life’s great inevitabilities, and it’s unpleasant, so we don’t tackle it much in cinema. In books a little bit more, but in cinema we don’t because cinema is like a dream and nobody wants to see a dream which ends unhappily. It’s why we tolerate it in a book. We have a level of distance. We pick it up, we put it down, we pick it up, we put it down over a span of a couple of weeks. A movie, you sit there for two hours, you’re hostage, and it unfolds unpleasantly. [Laughs] Man, that is not good. Now, I would make the argument that those pictures stand up very well over time. The key there is over time. In the immediate, we tend to want pictures which end in a very positive way.

So the key for Two Lovers was a somber and sober picture with as much humor as we could bring to it, but still about a very certain sadness and a purity in that sadness—not depressing, that’s a different thing, but sadness because sadness is beautiful.

It’s a film that’s so emotionally intuitive. I watching it when it came out, and it really awakened me to the idea of how much we idealize others, especially when it comes to romance. You’ve described how Gwyneth Paltrow and Vinessa Shaw’s characters each represent something different to Joaquin’s character, but that you’re not even sure he’s seeing who they really are. He’s projecting his own successes and failures onto them. I don’t think I’ve seen a film capture that concept quite as well as Two Lovers.
Well, thank you for saying that. I had read a piece of poetry. This is a little bit pretentious. It’s a piece of poetry by Louis Aragon, who was a French Surrealist poet. I had read this before Two Lovers, so I was trying to convey this a bit, and this is not a great translation from the French, but I’ll do it anyway. “In vain, your image comes to meet me / And does not enter me where I am who only shows it / Turning towards me, you can find / On the wall of my gaze, only your dreamt-of shadow / I am that wretch comparable with mirrors / That can reflect but cannot see / Like them my eye is empty and like them inhabited / By your absence, which makes them blind.” Meaning essentially, that when it comes to ideas of desire, we are absolutely clueless, because what we look for is in some ways what we lack, and we are blind. We don’t know the other person, really, and all of our desire is inherently superficial.

For example, I’m married now. I have a wonderful wife. I’ve been married now for eighteen years. We have three beautiful children. If I had gone to the party where I met my wife, and she had instead been wearing what I perceived to be too much or the wrong makeup or outfit, I could never have even talked to her. It tells you that our idea of desire is entirely about projection.

When you’re trying to convey that concept, it doesn’t matter what kind of loser he is or winner or whatever the word we might use for him is, and he lives with his parents in this crummy place and all that. The objective idea, “Oh, he’s a loser,” but that’s not what she sees. That’s not what Vinessa Shaw sees. She sees someone who looks like Joaquin Phoenix, a handsome young man who’s nice to his mother and a future business partner for her father. She sees very positive qualities in Leonard. We may disagree with her, but she’s thinking in a way about what she lacks and what she sees—what she wants, which is now what we see. That, to me, is the unending complexity of our desire. It’s like an onion you peel away. You never get to the center; it’s impossible.

Before we move on from Two Lovers, I want to ask about the ending. Some people see it as a bleak finale, in that he’s settling for his second choice. I’ve always read it as optimistic. He’s recognizing that happiness doesn’t have to be this grandiose “only in the movies” thing. I’ve always found it comforting, but I’m curious how it sits with you?
It doesn’t really have much meaning for me because I needing to get a closer shot. [Laughs] My memory is filled with the needs that I had on that day and all of that shit. I see a thing I would’ve done differently, or how I should have brought the camera a little this way. If that is the case—that you feel one way and other people feel another way—that’s great. That’s the best you can ask for.

My instinct is that it’s probably both, which is life! There are certain aspects of it that say his dream is dead, and that sucks. What’s also true is that this dream was probably bogus to begin with. But it’s what I said to you about movies being like a dream, particularly in the American context. Audiences are not really inculcated to expect, want, or even desire, or be in favor of films that present ethical and moral dilemmas that are unanswerable. So you tend to see reactions to that, even if they like it, being a little begrudging. “It didn’t hit completely for me.” Well, that really means, “I was left a little bit jarred by it,” which is something that actually I think stands up very well through time, and is an ambition of mine, to be honest. But they tend to test poorly.

To be honest, I’m really great at one thing, which is avoiding the Metacritic and Rotten Tomatometer thing—which I think is actually a very harmful thing for cinema, because it incentivizes homogenized pap. We’ve taught viewers to expect homogenized pap. When you expect something that’s a little homogenized, it means you’re expecting to feel good. You’re expecting an answer; you’re expecting a certain concept of narrative that I think is not a long-term answer because our lives are fraught, our lives are complicated, our lives are complex, and art must embrace this uncomfortableness. That is what connects us to others. It’s not, “Everything’s going to turn out all right”, because that’s not the way life is. Things don’t always turn out all right. Sometimes Hitler is around the corner. Sometimes it’s not always okay.

Someone, who shall remain nameless, a semi-famous person, said to me once about my most recent film [Armageddon Time], “I don’t think it’s good that you should make a movie in this moment about a subject that is so fraught.” I said, this is exactly the moment that you do that. I think his response was the response of the corporate person, and my response, for good or for ill—and I don’t mean this in a self-aggrandizing way—is what an artist should do. I mean, Picasso did not want Franco’s permission to paint Guernica, he did that because in the moment he had to do it given what was on the horizon.

I think that we confront these things to be complex, to be uncomfortable, to be ambiguous, to mean two things. It’s not vague. You know exactly what happens in Two Lovers. He goes home, he gives her the ring, the mother looks at him in a way that’s like she feels both miserable that he’s there but also happy that he’s back. It’s a very complicated reaction that she has seeing him there. But you know the physical actions; they’re clear. So it’s not vague, but it is ambiguous, and that’s the thing we should strive for, because that’s life.

I think The Immigrant is a masterpiece, so anybody who thinks you’re crazy for saying that can take a hike.
Some people, by the way, agree with that assessment, so that’s very nice. But I had an amazing time making it. It’s a very personal movie about my own grandparents and their experience coming to the country. I love Marion [Cotillard] in it. I love Joaquin in it. I love [Jeremy] Renner. I think that there is a level of myth that’s embraced by the film that I appreciate, and I think it's very comionate towards them. That’s something that I try to get at.

I loved the way they both acted the ending, which was, weirdly, shot on day three at the beginning of the movie. We had to work backwards, which I don’t mind doing because you have to know what the whole thing is anyway. But I thought what Joaquin says there, “You could lick my heart, you’d taste nothing but poison,” and her reaction to that, which was to hit him, and then leading up to the last shot in the movie, I very much communicated what it was I was trying to say.

Whether the movie is any good out there in the world, that’s for, I don’t know, Manohla Dargis or Justin Chang to comment on. But for what I was trying to say, it comes closest. That and Two Lovers come the closest, although now I really like my last film from that experience standpoint. It was like a home movie, and I shot it in my house—practically where I grew up. It’s about as accurate a representation as you could ask for from your own past. It’s very eerie. Because it’s like watching scenes from your own life play, which is weird, but also rewarding. I like those pictures, really. But what I think doesn’t matter.

[Warning: Spoilers for ‘The Immigrant’ follow in the next answer]

You mention the ending of The Immigrant, which concludes with this stunning shot—us watching her and her sister sailing away out the window, as Joaquin is reflected in the mirror walking back to New York. When did you know that was what you wanted the final shot to be?
That’s not a practical shot. There’s a lot of visual effects in it. Also, that was there from the very beginning in the script because the idea was, again, to embrace this idea of ambiguity. The idea was that she goes off to an uncertain future; he goes off to an uncertain future. That’s for you to decide. Now, again, we know literally what is happening. He walks off; she goes off on the boat. But that’s not the same thing as ambiguity. We don’t know their futures, and we’re going to wonder about them, and hopefully, it’ll linger in our minds. I knew it couldn’t be only about him because it wasn’t his story. I knew it couldn’t only be about her because in the end he achieves some kind of deliverance. So I had to have both in the shot.