Despite a title cribbed from Notorious B.I.G., writer-director Adam Leon’s first feature, Gimme the Loot, isn’t some dark, violent dive into the criminal underworld.

Instead, the sure-footed film is a much lighter, but still honest urban adventure that follows two New York City graffiti artists on the streets of the Bronx. Malcolm and Sofia (newcomers Ty Hickson and Tashi Washington) are hustling to raise the money they need to pull off a high-profile, legend-making graffiti tag.

Gimme the Loot was nominated this year for Best First Feature at the Independent Spirit Awards and Leon (who got his start as a production assistant on Woody Allen’s Melinda and Melinda and Hollywood Ending) won the Independent Spirit Someone to Watch Award.

I sat down last fall during the Chicago International Film Fest to talk with Adam Leon about his film, but in the process we ended up getting side-tracked into an enthusiastic discussion of current film makers whose work excites Leon.

Gimme the Loot is currently playing in select theaters.

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As I tell nearly every director these days, I’m getting addicted to naturalism, and I love how you use it here to ground the film in a realistic tone without being serious or somber.

Adam Leon: Stylistically it’s something that I’m drawn to – people speaking the way that they normally speak, in natural cadences. There’s not really improvisation in the movie—very, very little. Everything is scripted and every beat is scripted, but I let the actors use their own words when speaking casually. We wanted the movie to be extremely authentic in terms of its characters, language, locations, and the graffiti elements. But at the same time we embraced the idea that it was a movie.

You do a great job of balancing that authenticity with still telling an entertaining tale.

Leon: I very much wanted to tell a “movie story”—I wanted it to be an adventure. I was looking at the Bill Cosby/Sidney Poitier movies, even some of the Bob Hope/Bing Crosby road pictures. I wanted it to have that feeling and to play a little with heist movie conventions, and have a little bit of romantic-comedy conventions. I really wanted to structurally feel like an adventure, not just people hanging out. But then have the feeling in scenes of people just hanging out.

I like plot. I’m a huge fan of Sofia Coppola, and I think her movies have more plot than you think, but I just can’t make movies like she does, I don’t have it in me—I have to write lots of plot. But I wanted to shoot the scenes themselves at a languid place and have them feel very genuine and lived-in.

How do you shape out your story and dialogue in advance and then get that lived-in feel on the set?  

Leon: We’d done a lot of rehearsal and scene work and work-shopping, all of that. So we come in on set with everybody knowing their lines, and in their knowing what their lines are, as we do more and more takes, you can loosen it up a little. You can still know what your lines are and be able to change a word here or there in the moment, but most of the dialogue was scripted. But once we felt we had what we needed from the script, we’d play around and have fun in later takes and loosen up and try new jokes and incorporate new ideas. We didn’t shoot it with a lot of coverage and set ups, so we were able to do a lot of takes.

I’m fascinated by how shooting on digital is affecting and changing the way films are made these days, not just technically, but stylistically and tonally.

Leon: I think people can abuse that privilege and just shoot forever, which we really tried not to do. But at the same time, I don’t think we could have shot this movie in the way that we shot it in the length of time that we shot it. I’ve shot on film before, and I really enjoyed doing that, but it’s a different process.

And shooting on digital must be easier when working with a mostly non-professional cast.

Leon: We try not to be too high-stress on set, but shooting on digital just takes away one level of stress. I’ve worked before with non-professional actors and shot on film, and as much as you try not to, you can’t help but not be a little “Oh god, every single shot is costing us money.” You don’t want to have that thought.

It was really important for us in general to have a set that felt very welcoming, small, intimate, warm, friendly, and easy-going, because we wanted these mostly non-professional young actors to feel very comfortable. You can rehearse, but then all of a sudden it’s go-time on the set and all of a sudden there’s a big camera there. We wanted everybody to know it was okay to make mistakes, and shooting digitally helps with that.

We shot digitally, but we did a lot of camera tests – it was really important for us to have the film look like a big-budget movie. You can with digital now make a very sharp looking image. That wasn’t what we were going for, but my director of photography Jonathan Miller did a great job of creating a digital look that hopefully isn’t too flashy, that feels homemade. I was really impressed and happy with the look we were able to achieve.

Shooting on location also adds to the authenticity.

Leon: We wanted to capture a New York that you hadn’t always seen on camera, which was also a modern New York. But there’s a bit of a throwback feel and vibe. We knew that things were going to go wrong on location every day, but we embraced that.

We’d get to the set each day and see things there, like people playing dominoes, and incorporate them into that day’s shots. Sometimes kids didn’t show up, so we would go and find people in the neighborhood and put them in the movie. We just tried to be open to the location and not freak out when things didn’t go right. Which happened often.

I always love how early films shot on smaller budgets benefit from “happy accidents” and a sense of urgency and innovation. It seems the bigger a director gets and the more money they have in their budgets, the less they have to worry about not getting everything they want.

Leon: I want that problem. [Laughs.] However much preparation you do, there’s still that day, and you’re going to go out and create something that day. That’s really exciting, whatever level of support you have. I worked on a couple Woody Allen movies and watched this older master who really knows what he’s doing every year. But I would see him running around each day and changing things, like moving a scene from a soundstage to a new location he saw on the street. So you always have to be open to making the movie better. “How do we get this movie made, and how do we get this movie made better?” I think that’s a constant question that never ever goes away.

What other film makers do you admire or feel inspired by? Whose career would you like to have?

Leon: It’s hard for me to say, “I want that person’s career,” because I want to just tell great stories and what happens happens. But some working film makers today that I really admire for various reasons would be P.T. Anderson, a big, obvious one for a lot of film makers of my generation. Somebody who means a lot.

And I like Jonathan Demme and his career and how he’s able to tell so many different stories with different tones to so many different audiences, but there’s always a sense of himself in there. Soderbergh is somebody who I think also does that really well and is able to always tell stories at different levels and still make something that feels cool, no matter what it is. Olivier Assayas is one of the best film makers working today—I really admire his approach and attitude and vibe.

And then I think guys like Martin Scorsese are not too shabby. There are so many. Tarantino is a film maker who I’m there for every movie opening day. It’s interesting that P.T. is somebody who I’m there for every movie opening morning, sitting there kind of religiously, and Tarantino is a film maker I’m there for opening night with a 40 in my hand. I really love both of those experiences. They’re incredibly exciting film makers.

And just to keep this long list going, even though they’re so famous, I don’t think the Coen Brothers get enough credit—they’re such remarkable film makers. I think they’ve been on this incredible run recently, A Serious Man and True Grit and No Country for Old Men are all masterpieces. Those movies take a few viewings to sink in. There are also some young film makers I really like, the Safdie Brothers, Josh and Benny, whose Daddy Longlegs is a really great New York movie. And there’s a woman named Rebecca Thomas who made a movie called Electrick Children, and I think she’s phenomenal, a really exciting young film maker.

I think Anderson’s The Master is amazing. I’ve come to love and seek out films that take multiple viewings not just to “get” but to appreciate.

Leon: I sat next to these people when I saw The Master—I wasn’t with them—but when it ended, the guy turned to the woman and said, “I give it a ‘B’” I give it a B?! Don’t grade it! It’s not about that! This is a really fascinating artist at work, trying a lot of different things you’ve never seen. For me it’s such an exciting film. But when you’re operating on that level, it’s similar to a film maker like Kubrick, where even if you don’t love every moment, that’s not the point—he’s doing something more, and that’s deeply impressive and special, so good on him.

I also love how Anderson and Tarantino and the Coens are making films that also comment on the very nature of film and how cinema tells stories and creates meaning.

Leon: Some people can get on Tarantino for that, but I think he transcends it… usually. P.T. in The Master is definitely taking you to film school at times, but it’s about something more than just that. It’s not about indulgence; it’s not showing off, it’s about creating this greater cinematic experience.

One interesting common thread between filmmakers like Tarantino, the Coens, and Demme is that they love to play in and jump around from genre to genre. You certainly do that with Loot, with a little rom-com here, a little heist film there.

Leon: I wanted to make sure we kept the tone solid and steady and have this warm, fun tone throughout, but then throw in these different elements, like a frank sexual discussion or a heist scene. Let’s explore these kids’ lives over a couple days and the different conversations they get into and adventures they have, but hopefully keeping it as the same movie in the same universe.

I also like how Loot celebrates the joy of youth. There’s constantly a sense of all the darker directions this story could have gone with its setting and tropes. But it stays with that lighter feeling.

Leon: People come up to me afterwards and say, “I was expecting this other shoe to drop, but I was hoping it wouldn’t.” And that’s not Gimme the Loot. Even though it’s a very authentic world, it’s still a movie world that we’re creating. And it’s not a world where people are going to die—that was the start of the film, the beginning seed idea, to set something in this world that maybe you don’t expect tonally. I think the music helps a lot, saying, “Hey, this is going to be ride, an adventure; we’re going to have fun here.”