Philip Seymour Hoffman has earned enthusiastic acclaim for his acting work many times over. With Jack Goes Boating, he has announced himself as a formidable movie director, as well.

Hoffman’s feature directorial debut, based on the play by Bob Glaudini and scheduled for a September 17th release, centers on two New York couples, one in its ascendancy—Jack (Hoffman) and Connie (Amy Ryan)—and one in its decline—Clyde (John Ortiz) and Lucy (Daphne Rubin-Vega). The positivity of Jack and Connie’s relationship casts a stark light on the fractures in Clyde and Lucy’s, and before long all four characters are mired in the fallout of what Clyde and Lucy pessimistically call the realities of long-term relationships.

It’s the stuff that’s launched countless plays and films, but what separates Jack Goes Boating from the pack is Hoffman’s adroit and assured direction. In the Jack-Connie relationship, for example, Hoffman allows the camera to linger on what he describes as “the innate awkwardness of two people talking.” Like when real relationships are beginning, Jack and Connie have halting conversations while they tiptoe around the big questions. This approach could become ponderous, but under Hoffman’s direction it creates an honest, lived-in portrayal of love in bloom, propelling the film to a lean, filler-free, 90-minute runtime.

Here, old friends Hoffman and Ryan compare notes on the experience of working together on Jack Goes Boating, creating their on-screen relationship and the importance of working with actors who are a “good hang.”

Dante Ciampaglia (MM): You were both in Before the Devil Knows You’re Dead and Capote, but did you have a relationship outside of movies prior to making Jack Goes Boating? And did you draw on any of that for your performances?

Philip Seymour Hoffman (PSH): We met like 10 or 11 years ago. We were on this double-bill of one-act plays that were being done at the Barrow Street Theatre. We weren’t on the same one-act but we were on the same night, so I remember getting to know Amy back then. Then it was just acquaintances and through the business and stuff. But then we started working together again—on Capote and then Before the Devil Knows You’re Dead—and started hanging out more and talking more.

I don’t know if the relationship I have with Amy has anything to do with the relationship with the two characters in the film. What I do know is that whoever was going to play that part, I would need to trust right off that bat. I didn’t want to have to work at that. I didn’t want to have to put my time in and I felt that with Amy. So if anything, that definitely helped and was part of the reason why she’s in it.

Amy Ryan (AR): I feel like we have more of a working friendship and acquaintanceship. It’s not so much that we’re hanging out at restaurants all the time. Phil, you’re one of those people I’ve known for years and I feel I know well, but if I had to write down on paper the amount of social times we’ve been with each other outside of work, there’s very few. But the experiences we’ve had have been very true work; I feel, for me at least, it’s been very rich and intimate… And I think hopefully someday, if we do something else again, we’ll look back and think, ‘Wow, we thought we knew each other on Jack!’

PSH: Exactly. When you work together you’re put in a position of having to deal with each other and you can’t ignore each other. So you do get to know people in the work environment in short periods of time that in normal life might take longer, and that creates a unique relationship. Because you’re not in your own lives hanging out all the time but, like Amy said, you do have kind of intense little get-togethers when you’re working. I think the essence of that did help us trust each other when we were shooting.

I think of this flash of a moment when we were in Winnipeg doing camera tests for Capote. I saw you down the hall and I had just arrived the night before, so it was the first I’d said hello to you, and you were in your costume and hair as Truman and I said ‘Hey Phil, how ya doin’?’ You go, “Good… Yeah, it’s a scary one.” And then you were called away. And I just thought, ‘Oh wow.’

Then, the next moment, I’m sitting in the scene with you and I thought, ‘I have the front row seat to this incredible performance…’ It’s those miniscule moments… You could have completely just shot the shit with me like, “Hey, how was your flight? When did you get in?” But it was just this full, open-hearted moment when you said, ‘I don’t know about this one.’ (laughs) It’s those flash moments that maintain that bond, at least for me.

PSH: Absolutely.

AR: It’s the same with Before the Devil Knows You’re Dead; you were rehearsing with Sidney [Lumet] for two weeks in that intimate setting and I’m so glad you took that technique to Jack Goes Boating, which was key.

PSH: In the work environment, you’re kind of exposed. So these people that you don’t hang out with a lot in your life but you do hang out with in the work environment, you do see them in a much more revealing, exposed way. So you can go a year or two without seeing each other and when you see each other again it’s as if you saw each other yesterday. It’s because you both know a little bit of something about each other that you wouldn’t normally.

AR: That’s something I’ve always been curious about, because you and John Ortiz are so close. In scenes when you’re directing him in Jack Goes Boating, how much of your personal relationship was ever used as a tool? And I don’t mean in any manipulative way, because I’m sure you could take short cuts with him in some way. Did you find that you had a different approach with John because you do know him so well?

PSH: Not very often, but every once in a while, I’ll go over and say something to him that has to do with something that only we would know. But what’s great about John in that circumstance, because I’ve directed John a handful of times… when I put on that directing cap, John understands the difference between when we’re working together as director/actor and when we’re not. When we’re working as director/actor, John lets me direct. He becomes the actor and I become the director and it’s a really amazing thing… and it is a rare thing. With John it’s probably because we’re so close and have known each other so long. But also I think it’s because our relationship, from the beginning—from our first meeting—has been forged through creating work. That’s what we do together. I don’t know if I have that relationship with anyone else that way. It’s very unique with him. So we just kind of let it happen; we try not to get in the way of it.

MM: Were there any surprises you learned about each other on this movie?

PSH: No, I didn’t learn anything new. I was so happy to be reminded that Amy is exactly who I thought she was, which is a thoughtful, talented, serious actress who also likes to have a good time—and that’s essential. (laughs) Those are the qualities. So I guess you get surprised by the thing you assume, but a lot of times you get disappointed and that’s life. You disappoint yourself all the time. I felt that more about myself while shooting, if anything. But with Amy? No.

AR: I’ve seen your work as a director before in terms of theater, and I wouldn’t say I was surprised. I was in good hands. I never doubted it. “What was Phil like as a director?” That to me would never be a thought… You’re creating a beautiful film from a beautiful script. Why wouldn’t anybody want to be there with bells on? I think with your passion for your work, it’s impossible not to be affected and encouraged by that. When I see your films and know nothing about the project that you’re working on, I just go as a moviegoer and pay my $10.

MM: There was very little artifice between the characters and their relationship in the movie. How did you work together to make each other’s relationship so real?

PSH: That’s a really good question, because I don’t think that’s something you can work on. I think that, if I’m honest, other than the rehearsal that we did and the debate and ongoing discussion, there’s also an aspect that I’ve kind of left alone… which is the innate awkwardness of two people talking… (laughs) like right now.

I think truly communicating with another person is difficult and I think a lot of our personalities and behaviors are made up of ways to deal with that. Either to make it look like it’s not difficult or to make it look comfortable or savvy or coy or whatever we do. I think that with Connie and Jack, neither of them are really good at covering up what’s going on and they’re a bit transparent as people in general. I remember saying, ‘Leave it alone’ sometimes when we were working on those scenes to let any awkwardness or uncomfortability or anything that was happening just happen. Don’t try to do anything about it.

AR: I remember rehearsing that hospital scene and not quite understanding it. I remember looking over and thinking, ‘Maybe I don’t understand what’s going on with Jack and what’s happening with Connie’s emotions.’ Phil, as a director and an actor, is comfortable with a pause and letting that air be there and not cutting away to 1,000 different reaction shots and letting that sit in the air between them. I think that’s where the truth lies.

PSH: I think Bob Glaudini, the writer, who I’ve known for a while… I think that’s in the writing. I realize every time I keep reading it or working it out, I think, ‘God, the writing is asking you to not get out of how uncomfortable the situation is.’ It actually goes forthright through it and right into it. (laughs)

AR: (laughs) It really is the most fun route, as difficult as it may be.

MM: Does being an actor make you a better director, in general?

PSH: To be honest, I think being a director makes me a better actor more than the other way around. I think that since I’ve started directing, I’ve definitely learned more about myself watching other actors than I did before, because being an actor is a highly subjective position. You really do need somebody outside to watch but, as an actor, sometimes you think you know better. I know I’m like that.

When I started directing I realized that a lot of times I don’t know better and I need to listen. I need to trust and collaborate. I have a lot of habits and ways that weren’t helping me and I didn’t understand that until I saw it in other actors.

I think I’m still trying to grow as a director each time I direct… I think now that I’ve directed one film, and if I get a chance to do it again, I know each film will be different and have a little difficulty, but acting is the hard job on the day. To be vulnerable and open in front of a bunch of people all day long is not an easy thing. Being an actor has helped me with that aspect of it.

AR: I think the beauty of being directed by an actor is a shared language. Not that directors don’t have that but, as Phil said, like knowing what an actor goes through to get to a place and to be open and exposed—or just to try and be willing to fail—is a scary place to go. But there’s no alternative, really. Actually, the alternative is mediocrity and that’s worse. But you still need a nudge. You need someone to catch you.

What Phil brought as a director and experience that I’ve never really had before is a multi-layering, because I know Phil understands well how human behavior works… I feel like Phil gave the whole roadmap. You can see all the different avenues to get to this place, which I think makes it more interesting to watch. Phil has the patience and the passion to find that nuance.

MM: Is there anything that came up during the shooting that you wanted to ask each other about but didn’t get around to that we can talk about now?

PSH: We’ve been asked that question before. It’s a good question because I think I am surprised a lot of the time when I work with people, because you have an assumption about them which is usually wrong. It’s just kind of how life is. It’s usually wrong in the positive way, meaning you learn a lot about somebody in a very positive way.

AR: I’m deathly afraid of people who don’t take it seriously, but I’m afraid in tandem of people who take themselves too seriously. We have to laugh at ourselves from time to time, or I don’t know how we really get through this. I think we had a tremendous amount of belly laughs and that helps any situation, especially if it’s late at night in the freezing cold on location. You’re also so happy to be there. Maybe you’d want to get into your bed at this point and stop putting those little hot pockets under your neck or pants pockets or anywhere else you might find a place for them, but being around Phil is a reminder of how rich and great life is. Why not grab it?

To me, that was the experience of Jack Goes Boating. This company, this experience, this role—they don’t come around often. I remember saying ‘yes’ to this script right away, and not knowing how in the hell to start working on Connie. I didn’t know who she was for a very long time. Even in scenes while we were shooting, I wasn’t quite sure where we were going. But with Phil’s encouragement it was like, “Let it be. Let the awkwardness be there and she shall come to us.”

PSH: Our mutual friend, [Capote director] Bennett Miller, has a saying, if “somebody is a good hang.” He always says that. We’ll talk about somebody I don’t know and he’ll say, “Oh, they’re a good hang,” or “They’re not a good hang.” I think that’s important. Amy’s not difficult at all but there are some actors, people and directors who can be difficult, including myself at times. But if they’re still a good hang, it’s okay.

You have to be willing to sit with somebody. Filming is a lot about hanging out. And if you have an issue with that, it’s going to be an problem. When Amy’s talking about being cold, we always harp on this one scene because it was so fucking cold. (laughs) The scene where we had that first kiss outside. I mean, literally, it was zero or something—it was freezing. There were times where I just couldn’t sit outside anymore because I was directing and I’d go sit in the car. We’d all be sitting in the car and you have to be able to do that. You have to be able to sit in a car where nothing is said for 10 minutes and the heater is on and then someone cracks a joke or someone says, “When is this going to be over?” MM