This article is part of a series of interviews with leading filmmakers and craftspeople, made possible with special support by the Academy Foundation of the Academy of Motion Picture Arts and Sciences.

Roger Greenberg is a slacker past his prime, an acerbic fortysomething drifter whose vulnerability is barely concealed by layers of self-loathing, defiant lassitude, and the sharp wit he wields while either fending off intimacy or partaking in his favorite hobby, writing complaint letters to corporations. Noah Baumbach's new movie, Greenberg, opening in New York and Los Angeles on March 19, follows its title character, played by Ben Stiller, on a housesitting trip to California, where he hopes to "do nothing" but tentatively falls for his brother's personal assistant (played by Greta Gerwig), an equally lost soul in her mid-twenties. Set in an oddly gray and deglamorized Los Angeles that feels like a city where dreams go to die, Greenberg plays like a bracing homage to the alienated splendor of 1970s American cinema. Baumbach co-wrote the film with his wife, Jennifer Jason Leigh, who makes a memorable cameo as an old flame of Greenberg's. Baumbach and Leigh live in Los Angeles, and thanks to their vision and Harris Savides's lucid cinematography, Greenberg has a lived-in, authentic sense of atmosphere.

The film contains Stiller's best screen performance to date, harnessing the restless comic energy of his earlier work and adding layers of contradiction and confusion. It is an astute character study, a raw and rambling movie that breathes with the messiness of real life; in other words, the type of film more likely to come out of Austin, Texas, than from the city in which it's set. There is an autobiographical component to Baumbach's earlier films, including The Squid and the Whale and Margot at the Wedding, but Greenberg is hardly as insular as its main character. It's a tough and tender movie about a world where intelligence and emotional maturity don't often go hand in hand.

Baumbach is an ardent cinephile; his artistic sensibility is informed by the movies that he's seen, yet he is keenly attuned to the inner lives of his characters and his actors. Our phone conversation took place the day after I saw a new print of Bob Rafelson's Five Easy Pieces (1970). A quirky, unpredictable film that was clearly written for its star (Jack Nicholson), and centers on a character as deeply flawed as he is compelling, Five Easy Pieces reminded me, in an odd way, of Greenberg.

I just saw Five Easy Pieces. And I was thinking about how great that film is, because it seemed so organically written for Jack Nicholson. And Greenberg had some of that feeling to me, of being written for a specific actor. Could you talk about the way it came about, in relation to Ben Stiller?

That's funny because Five Easy Pieces is a movie I keep buying new copies of, because I keep watching it. For totally different reasons. But each movie I make, I keep looking at it, at some point in the prep period.

That makes sense because it has a certain rhythm that's like your films. You never know where it's going, but it feels totally lived-in and authentic.

Yeah. It feels made up as they went along. In the best possible sense. I mean, there's some movies that feel made up and they're terrible. And you think they should have planned it. But this movie feels improvised in the filmmaking, as opposed to in the dialogue.

That quality is true of your films too.

Yeah, I'm trying to remember. For Margot, we looked at Five Easy Pieces, because there's all those great scenes when [Nicholson's character] goes to the island, on the ferry. Just the colors. There's a lot of great details—like, even the sweater that Lois Smith is wearing when they're playing ping-pong.

I wanted to focus on a few specific scenes. First, the restaurant scene, when Greenberg celebrates his birthday with his friend. The one that ends with that great line, "Life is wasted on people."

Could you talk about that scene? It has this great combination of being lifelike, with characters stumbling around for words, but it also has these very sharp lines.

Yeah, because in the parameters of Greenberg's life, going out for a nice dinner is a major event. Ben and I talked a lot about it when we were preparing. He's almost vibrating with a little giddiness, and he's sort of into the fact that he's impressed with himself. He says, "I'm weirdly on tonight." This is like the good version of himself. I think Greenberg has had many dinners with friends where he probably was reaching for bons mots and missing. He feels like he's actually on. And I think that that makes him more expansive. It's what makes him want to invite Florence. It also makes him go and ask out Beth [Leigh's character] at the same time. It's almost like he's feeling good enough that he pretty much would like to try to get everybody he knows into the room at that point. At the same time, I think it's—as everything is with Greenberg—it's cut with a sense of, "Is this the best version of my birthday? Should I do this differently? Am I doing this right?" I'm sure once he starts to feel good, he starts to question that.

Right, and he conveys that to the people he's with. So he makes them feel like, "I don't really want to be with you."

Exactly. I think Greenberg's somebody who probably when he gets home, he wishes he had people around. And then as soon as he's with people, he wishes he were home. And I think it also dramatizes his and Ivan's relationship quite nicely, because they really are talking over each other. Neither is listening to the other. Or at least Greenberg's not listening to Ivan.

The way you're describing it justifies why this character would be coming out with these witty lines. So it doesn't feel like it's you, as the writer, showing off. It feels like he's sort of impressed with himself.

Yeah, well, Greenberg's a handy character. He's a fun character to write, because you can show off a little and get away with it [laughs].

You did the same thing with Jack Black in Margot, where you work with a comedian who has a very strong comic persona. You keep part of that, but also show a darker side.

Right. Well, a lot of people will say to me—and I understand why they say it—"Oh, we've never seen Ben like this." I totally get that. But at the same time, I feel like, so much of Ben is used in Greenberg. I wanted what only Ben could bring for this part.

I think what you're seeing is aspects of Stiller that have been in the other films, but you're bringing them out in a new way. And I think he's also going to a deeper place, too. It feels like you were getting at something personal, in the way that, to get back to Five Easy Pieces, it feels like the screenwriter for that film, Carole Eastman, really knew and understood Nicholson.

What really works about that movie, which is what you're saying, is that it's a movie made by people who clearly knew each other well. That movie could only work with people who were that comfortable and that familiar with each other. Also, when people are too comfortable with each other, those movies sometimes feel indulgent and don't work. But when they do work, you get Five Easy Pieces.

In terms of the Los Angeles setting and the overall tone of this film, were you consciously thinking of these 1970s American films? Or were you dealing with your own feelings about being in Los Angeles?

I was really dealing with my own feelings about Los Angeles and Harris's feelings and Jennifer's feelings and that was really what was in my mind, certainly, in any practical way. But I had all those movies in my head. I wanted it to be a movie in that tradition, of 1970s L.A. movies. I felt that those directors really did show L.A. in a way that was so personal and particular and totally unique. The movies, they're all very different. So I sort of was aiming for that, but I was using my own observations.

The other scene that I wanted to talk about from Greenberg is the scene in the waiting room at the animal hospital, with Florence and Greenberg. The dynamic between the two of them is so interesting throughout the film. You totally understand the self-esteem issues that make her fall for him. You can see why they're kind of right for each other, in a bizarre way. Yet he's quite obnoxious toward her, especially in the beginning, when he's taking advantage of the power he has over her. You see this in the scene at the vet's office, when he has her go ask about the dog.

When I cut that scene, I remember talking with Jennifer [Jason Leigh] about how anxious he was. It's so hard for him to be there.

You see all that physically. He's twitching.

Yeah, he's almost bent over in pain. Whereas I think for her, this is the kind of thing that she does some version of every day. Doing something for somebody is something that she's very comfortable with.

That's her livelihood.

It's her livelihood. And I think probably also something she does in her regular life. I'm sure she's the kind of person whose friends will ask her to take them—pick them up at the airport or help them move or something. So I think what I like about that scene is you have two people in two very different comfort zones. But at the same time, what I was going to say is when we cut that scene, I kind of felt like these people belong together in some way. That there's something chemical going on in that scene that, for me anyway, makes them feel very connected.

There's a way that he looks at her, right before she goes up. You can feel a genuine kind of affection—there's something coming from him that feels real.

It's actually one of the few times I extended the scene beyond the script. Because the script ended with her going to ask about the dog. He asks her how long it'll take, and she says, "I don't know. You know, they seem busy." And then he says, "Should I ask?" And then she says, "Okay." And then he says, "Do you want to do it?" And that's how the scripted scene ended. But it was one of the few times I felt like it should be broadened, because something else was going on in that scene. So we came up with, on the day, her going to ask and coming back—her giving him the information, but him saying, "I could hear you."

So you have that moment when he's watching her as she's walking across the room. You give space for that to happen, for us to think about what's going on inside his head.

Yeah. When we shot it, I thought, maybe we indulged on the day of shooting, but probably when I cut it, I'll end up just using what I had in the script. But when we saw the whole thing, it felt right for the movie.

Could we talk a little bit about Margot at the Wedding? There's the section that starts with Jack Black and Jennifer Jason Leigh's characters going to confront the neighbor. And then they walk back and he talks about how he just wants to beat up Nicole Kidman's character. You see all these sides of their characters. It starts off with her mad at him because he was such a wimp in that confrontation. And then he lets all this anger come out. She resents him, but then she laughs at him. Then it ends with them making love. There's all this stuff going on. And anger is one of the main issues of the film. He's childish, but he shows his anger.

Something I always felt in that movie is that that relationship is actually really strong. And even though Nicole's character has this idea that he's a symptom of Jennifer's character settling, or that she's not challenging herself properly, this isn't the right person, I actually felt—and I wanted it to come across in that scene—that these two are actually, almost in a screwball comedy way, kind of meant to be together. Or if not so much meant to be together, that they actually have something that really works.

In a funny way, there's something healthy about him, compared to Margot, who is so uptight.

Well, that's the thing. And even with his freak-out, he is getting it out, you know? And I think that's why they end up having sex. For her, there's something very attractive about that, that he's able to express all this, get this hostility out. And also that they could kind of fail on this mission and work it out in their odd way. It ends also with her laughing, after he gets angry. And I think it's because she kind of understands that and doesn't take it too seriously.

You don't feel like it's a really mocking laugh.

Right, it's also a relief. I think both of them, in that scene, are able to let go, in a way. That's something that Nicole's character has a really hard time doing.

I'm interested in the difference between the scene as it came to life while you were directing it, versus how it was on the page, because so much of what works has to do with the dynamic of the performers being in that moment.

Well, it's not unlike that waiting room scene that you mentioned from Greenberg, in that I felt in both cases, the actors really—the vibe of their interaction just really crackled for me. And I really enjoyed shooting that sequence because Jennifer and Jack—you wouldn't necessarily have thought of those two actors together. But I think they made a kind of strange sense.

It's true about the characters, but I think it's actually really true about them as actors. I know they both really loved working together for that reason, too. And it was very fun to shoot because we shot it in really long takes. I remember we had just enough film to bring them in, have them have the confrontation with the neighbor, and then go out and shoot the whole rest of it. You don't see all of that in one take in the movie; I cut between them. But it was the kind of scene that, because it was working, I felt the freedom to shoot it more raggedly, to let them just keep going. I would cover Jack more on one take and cover Jennifer more in another one. But I kind of knew that they were in the kind of zone that I was going to be able to use different takes. Sometimes when you do that, you get takes that are so different in energy that you can't use them together. It's difficult for Jack too, because he had to kind of explode, but build to it at the same time. Which is why I also wanted to try and run it as long as possible—from the beginning, to let him have the experience.

As soon as you mentioned screwball, I thought of Howard Hawks. I've read that you are a fan of his, but I don't know if you were sort of thinking of him while directing that film or—

I think of this sort of Hawks kind of dialogue, and even the overlapping style that he uses in so many movies. I think in my way, I always have those movies in the back of my head. A major difference is that he embraced a certain stylized comedic aspect, and I am going for something that maybe feels more—

Naturalistic?

Yeah, naturalistic.  But at the same time, I don't think they're that far apart.