With his directorial debut, Dean, comedic multihyphenate Demetri Martin stars alongside an impressive ensemble cast in a bicoastal comedy-drama about loss and grief.

Foremost a stand-up comedian, Martin cut his teeth as a writer for Late Night with Conan O’Brien in the early 2000s. His profile rose considerably after his 2007 stand-up special Demetri Martin. Person., which gave the world a face behind his trademark clever-absurd wit, and showcased his talents for guitar strumming and drawing. In the decade since, Martin’s had his own (short-lived) series at Comedy Central, and moved more seriously into acting, taking the lead role in the Ang Lee-directed 2009 comedy Taking Woodstock, and appearing in films like Steven Soderbergh’s Contagion and Lake Bell’s In a World…

Dean follows the titular character (Martin), a cartoonist struggling to meet a deadline for a new book of drawings because he’s far too busy wallowing in a muted state of grief following the death of his mother. A strong visual element of the film are Dean’s death-obsessed drawings (drawn by Martin himself) which feature prominently and effectively in the film. An impromptu trip to Los Angeles allows Martin to have a bit of fun with classic L.A. tropes, while introducing Dean to Nicky (Gillian Jacobs), who quickly complicates his commitment to wallowing.

Dean’s father Robert (Academy Award-winner Kevin Kline) is following a more traditional model for getting through grief: maintaining a rigorous regime of exercise combined with self-help DVDs and books. It’s clear that neither man’s approach is sustainable, though, and the film navigates their mutual paths toward healthier places with a light, sensitive hand. Dean premiered at Tribeca in 2016, where it took home the festival’s Founders Award for Best Narrative Feature.

Demetri Martin and Gillian Jacobs in Dean

Caleb Hammond, MovieMaker Magazine (MM): Dating as far back as Annie Hall, there’s a rich history of comedies that straddle both Los Angeles and New York City. What perspective were you hoping to bring to this conversation?

Demetri Martin (DM): I’m someone—like many people—who came up in New York, spent a lot of time here, then moved to California. It’s been eight years since I’ve moved. What I thought I could contribute to that conversation was looking at both places that many of us know very well, certainly through films and television, through the lens of a guy who’s trying to escape something in his own life. He’s just looking to take a break, to just get away; he’s not someone who’s drawn to L.A., or really particularly wants to be in L.A. But what I found in life is sometimes a place can really change for you if there’s someone there you care about. You fall for someone, or your best friend moves there. You have one sense of what the place is, and then it’s like putting on a new pair of glasses, or looking through a different lens. I liked that idea. And I wanted to stick it to L.A. and New York. I don’t think either place is perfect. I think it’s easy to love New York, and a lot of people pick on L.A. But there are some great things about L.A. too. So I thought it would be fun to kind of stick it to both of them.

MM: As a first-time director, what processes did you feel you were prepared for, but once you got on set you had to learn as you were going?

DM: I had ideas about how I wanted to tell the story. I didn’t feel too lost. I didn’t ever feel like, “Oh geez, I don’t know what I want here.” What happened, though, was that I learned about compromising and about reality vs. your ideas about what you think you’re going to do. Because the film’s budget was under a million dollars and it was a 20-day shoot, it was extremely challenging. I didn’t know what I didn’t know. I had a company move across the country in a 20-day shoot. Well, now I know that’s a kamikaze mission. I had a lot of locations; we did a lot of moving when we were in each city. Now I get it: That’s crazy. That’s part of your day—the clock is ticking. That meant fewer setups, fewer takes, not a lot of time to light stuff. My DP, Mark Schwartzbard, did a wonderful job with what he had to work with.

I made things much harder for myself without realizing it going into it. I like working with the actors. I wanted to do less coverage when possible. I wanted to have more two-shots, or three-shots—however many people were on screen, so that your eye could travel and the actors could be more connected. I also tried to cover myself, because it’s my first time around and I wanted to have some flexibility in my edit. I wanted to account for my drawings. I shot it anamorphic so that I’d have space there to have the drawings take up half the screen, so that you have live-action footage next to a drawing. There’s something interesting that can happen in that juxtaposition—it’s like a dialogue between them, the action and the little cartoon.

What was hard was the producing. I found problem-solving exhausting, and that’s really what kept me up at night. I tracked though storyboarding and overhead and all this stuff, but it turned out a lot of times we didn’t have a location until the day before. There were at least two times where we finished a shoot day and we still didn’t have a location for tomorrow. But we had to shoot. I couldn’t not shoot. That stuff was really rough.

When I actually got to do what I thought the work of directing would be, I found it really stimulating and really fun. Unfortunately, I guess you remember more traumatic things. Things with more emotional weight are the ones that stick with you. For me that was all, “There’s no place to park the trucks. Tomorrow’s location fell through. This actor’s no longer available at this time.” I was like, “Holy shit.” I had these fantasies like, “Oh, I’m going to do my pre-recording. I have my shot list.” Then you get there and you have to do it in 10 minutes.

I liked post-production. There’s a lot of hope in the edit. Yes, you have to deal with the reality of what you shot, but I thought, “Cool, I have a clean slate here. Let’s see what we can make out of this curio.”

MM: What was your process working with your team to craft a visual style for Dean?

DM: This was one of those reality checks, because when you look at how long you have to shoot whatever pages you have, the constraints just start to pile up. I realized quickly that some of the things I wanted to do, there was no debate; they just were not even possible. I was really happy with my DP’s work. His temperament was excellent. He worked really fast. He did really well with what we had. His kit was very small, and we had to make choices. It’s a zero sum game. You just can’t afford it all. We shot on an Alexa, which I like a lot; it’s a great camera. We shot on Japanese Kowa lenses. That was interesting because the lenses were cool; they were imperfect but it gave it a lot of light in the lenses, and they were forgiving. They weren’t so austere and technical, showing every detail the way that a lot of today’s technology can do. The 40mm [lens] was really fucked up; there was some weird stuff going on in there. We would put it on, and it was kind of distracting. We ended up not being able to shoot too much with that lens.

We watched The Landlord together—the DP and I, the week before we started shooting. I talked a lot about Hal Ashby. That was cool to watch that with him and to talk about it. I watched Shampoo on my own. I liked looking at how Hal Ashby used the camera, some of the movements and how much you could do without moving that much. When you lay a little bit of track and you can move, but then you can pan. It was cool seeing movies that I love with those eyes, talking about them: “I liked that kind of warmth.” Mark would say, “Yeah, I think I can do something like that. We can get a little bit of track.” That was really helpful.

MM: Talk about directing yourself: Is that a nerve-wracking process—not being able to look at the monitor and not having this bird’s eye view of the process because you’re in the scenes themselves?

DM: That was a trade off. That was difficult. I got lucky to get a guy like Kevin Kline to be in the movie. I realized quickly that I wasn’t going to stop and go look at the monitor and have Kevin waiting here just so I could look at myself. A couple of times I decided it was worth it: “I’m going to go look just to make sure after we do a few takes. Take two felt good; let me see how it looks.” I could adjust a little bit.

Martin and Kevin Kline, who plays Dean’s father

I think I’m self-aware enough to realize my range is pretty limited as an actor. I wasn’t trying to go too far out of what I know how to do. So that helped a little bit too. I wasn’t making The Godfather or Kramer vs. Kramer. My DP, my first AD, my set designer or art director—what emerged was a group of us there who developed a shorthand, and I said early on, “Hey, do me a favor: If you ever feel weird or you think I’m off, I’m open to whatever. I’ll take any notes.” I remember once the DP said, “You might want to do that one again. You were coming across kind of angry.” And I was pissed, because we didn’t have a location for the next day! I’m not a good-enough actor for that not to seep out. You have to learn how to compartmentalize. The trade off is great though. You get to the edit; you can tweak; you can protect yourself; you can change your story if you need to. Getting to be in the scenes is great, because as they say, you write the movie three times: script, production and the edit.

MM: In your relatively small selection of acting credits, you’ve managed to work with some great directors like Ang Lee and Steven Soderbergh. What directing lessons did you glean from working with them as an actor?

DM: There were a lot of little things. I tried to pay attention when I got to work with those guys, because I knew then that I wanted to make films. It was cool seeing Ang talking to Eric Gautier, DP on that movie, about lenses; also about the order in which they were going to shoot things. Seeing him work with some of the bigger compositions for Taking Woodstock. There were some shots that had such depth, because there was a big field in the background. There would be a van coming in on this side of the screen, a family on a blanket, some people walking by, a guy on a motorcycle here. To see him figure out the shot almost in steps—as if he started with the deepest field of vision, the furthest radius, and in those layers got closer and closer to the camera, where the last two things in the shot were the people—it would be me and Jonathan Groff—and he would position us. It was really technical and very educational.

Soderbergh was amazing; that guy works so fast and is so precise. He was behind the camera. It was incredible. In both cases, I saw two really talented directors surrounded by people they trusted—they really had their team. You could see how efficient that made things and how well people worked together.

The number-one takeaway for me was that directing is a performance. I never realized that before I was on their sets. Whether you want it to be or not, on the day, every day, you are being watched: your body language, your tone of voice, how you move through that day—everyone’s looking to you for answers. You’re steering the ship. That was something I tried to be conscious of going into this. Even though I was tired and overwhelmed with trying hard to get this movie to come together, I tried to think about what other people were going through and what signals I was giving people who were working for me and with me. Especially on a low-budget movie, because everyone is doing you a favor. That was a very helpful lesson; it taught me a lot about empathy and thinking outside of yourself. Stand-up doesn’t teach you that, necessarily. It teaches you about your own comedic voice, and how to do shows and listen to the audience and pay attention. It teaches you vigilance, things like that. You don’t have scene partners. You don’t have a DP. You don’t have any of that.

Drawing by Demetri Martin

MM: As a creative person who works in so many different mediums, how do you budget your time and decide what you’re going to spend your creative energies on?

DM: Deadlines help me a lot because they move something up on the priority list. That definitely helps me prioritize. When I’m left to my own devices, I always start with stand-up because that’s still basically where I make my living. Stand-up is still very important to me, and I do try to write jokes all of the time. When I’m getting ready for a special or a tour, you have such a real deadline; it has made me more of a grown-up. When I started, I used to just go for walks in New York and daydream and jokes would float into my head and I’d write them in my notebook, and I’d try them at night. But then you do one, two, three hour-long specials and all of that material is gone. I put stand-up in my series [Important Things with Demetri Martin] when I had it. I look up now and it’s like, “Holy shit. I used up a lot of ideas and material.” Now, especially when I’m getting ready for something, I have to sit down and write. I have to say, “OK, write a page of jokes,” and treat it like a real job. Screenwriting is really important to me, because I want to make films. So that’s very time-consuming. I’m still trying to figure it out. I find it really challenging because I don’t want to not spend time with my kids or my wife. That’s my life. It does feel like some of the social time or down time—that seems to have disappeared.

I’m so psyched I got to make a movie, and it got distribution. Whatever people think of the movie, I beat the odds, because it exists. It is crazy to try to make an independent film. When you try it, you realize, “Oh my God. So many things have to go right for this to even be out there.” But then when you get what you wanted, the answer is just more work—trying to sell the thing. That’s one of the things that I find most challenging. When I’m trying to tell people about something that I made, it shuts down that other part of my brain—the part that writes jokes and comes up with story ideas. I like to paint. You kind of have fun creatively. But that’s not being a grown-up. That’s a luxury. Now I get it. The grown-up part is finishing it and selling it and raising money and all that shit. I’m like, “Holy cow.” No joke.

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