Set in New York City, Gimme the Loot is the story of two graffiti artists, Malcolm (Ty Hickson) and Sofia (Tashiana Washington), who want to make the toughest tag in the city: the New York Mets' Home Run Apple. But before they can mark up a city icon, they need money to get into the stadium first. This is Leon's first film, coming after his debut 2009 short Killer. Previously, Leon worked as a set production assistant on Woody Allen film Hollywood Ending, and as a production office assistant on Melinda and Melinda.

Speaking with Leon during Loot's presentation at last year's Chicago International Film Festival, we discussed his film, the storytelling trend of other first-time directors, how he strives to make someone's favorite film, and more.

Gimme the Loot is currently expanding to select theaters.

Given the presence your film had at Cannes and SXSW, did you and your filmmaking crew have any rock star moments at these festivals? Or any humbling moments?

I think the whole thing is humbling. In some ways, I think even the success is humbling. We don't have a three-picture deal. I think we had a rock star moment at the Cannes Film Festival, because we weren't expecting anything. We went into it with low concern, like we did with SXSW. "They can't take away our laurels." We did it up. You go out meeting people, you put on a tuxedo, and we tried to not be arrogant. We said, "We're allowed for this week to be like, 'Fuck yeah, we did this.'" When you screen the movie at Cannes, they're blasting your soundtrack outside, and then there's a standing ovation, which is pretty common there. But still, that was just like, "What the fuck."

In the movie your character Malcolm is constantly only wearing socks while walking through New York City. Was he wearing any padding underneath those socks? We had him in padding for the first hour that he was in socks. He said it wasn't working, and that he felt less comfortable, and you also have to make sure you can't see that it was padding. We just tried to make sure there was no broken glass where he was walking. It was hard on his feet. But he was so game for it, and so focused.

Was it more liberating or stressful to make this film in a guerrilla style?

We tried not to be too stressed. We expected that when you shoot the movie this way that everything was going to go wrong, and it did, often. But that was okay. The key parts weren't going wrong, the key parts being that we had a great cast and a great crew, and we had done a lot of team building and preparation. That was there. We weren't going to break. We loved each other. That may sound lame, but it's true. When things went an hour overlong, it was okay. It didn't really freak us out. We were lucky that nothing incredibly difficult happened. Ultimately I had fun, and I think others did too.

When you were making this film under such conditions, did you often stick to a script or no?

[The film is] very scripted, more than a lot of people think. Even the dialogue was scripted, although I encouraged them to use their own words. There were edits on set; I think we had to be like that.

Did you have other feature ideas before you made this one? Why did you choose this script over others?

I had written other scripts. I think there was a reason that this one jumped out, the key one was that I felt that this movie should be a first film, and have that whole new feel to it, which would be right for the story. I thought the budget level was right, I felt I could raise a little money but it wouldn't be a million dollars. I felt that this movie would be worse with a million dollars. The writing started when I found Malcolm and Sophia in my head, and was able to sort of hear them just walking down the street thinking about they were talking about. I really felt like I knew them.

Are the characters based on anyone you've known, or know now?

I knew Ty [Hickson] who plays Malcolm, but he's very different from Malcolm. There's a bit of him as a 15 or 16-year-old in that. There's a little bit of me I think in that too. And Sophia, she's like me while hungry.

It's really interesting exploring these characters. She's a 17-year-old African American girl, and how does that relate to me? And how does it not? And how can I identify with her? That exploration was one of the fun things I found in writing. I thought that was more interesting than writing about a 28 year old white guy, because I've talked with him, and he's not interesting.

Has there been any type of backlash to you using black characters despite being a 28-year-old white guy?

Before I even started writing the script. I think there's a few elements of that. The process was really organic in the sense that I knew Ty (from previous short film Killer) and I wanted to work with him again so I built this character around him, and so it made sense for Sophia to be Latino or African American. I think there was an organic process to that. I also see the movie as a movie about a place, New York, and it features a lot of different cultures. And finally I don't think the movie is about black self-identity, it's not a biopic of Stokely Carmichael, I think the fact that they are black informs these characters, but it's not necessarily about that journey. That is a journey I don't think I'd be able to tell, or it would be subjective subconsciously. We worked with a very diverse cast and crew. You could say the author is Caucasian, but I think there are a lot of authors in this movie.

Many first-time filmmakers seem to want to make a movies initally about something that is very much about them. Were you conscious to of this quality so much that you wanted to distance yourself from that type of story?

No one wants to see me in a movie, that's ridiculous. I was not interested in exploring just my life. I felt like I could explore parts of my life through a different world, and wanted to make something for an audience, that I would go see and like. Most of those movies, can really about the romantic trials and tribulations of someone in their 30s. For example, the new Baumbach is phenomenal [Frances Ha], and I didn't think I would love it because I don't think that subject is interesting, but he nailed it. It's very difficult to nail, and it's not something that's interesting to me at least at this moment. I wanted to make a cool movie, and I'm not that cool. Well, I'm kind of cool because I made this movie. I'd be a lot less cool if I made a movie about "My girlfriend broke up with me."

Do you see yourself shooting mostly New York stories, or filming somewhere else?

I'd like to shoot somewhere else. I love shooting in New York. I want to tell stories. I want to make movies that could be somebody's favorite of the year. And that could be a very different kind. I just want to tell stories that come from me and excite me, and are ultimately about taking the audience somewhere. I get these scripts, but I say, "This isn't going to be anybody's favorite movie."

Quick Questions with Adam Leon

Favorite fruit? That's a tough question. Blueberries are delicious, but apple needs love. I can go tropical though, and do a little mango.

If you could be someone else for 24 hours? One is to be Obama, but that sounds terrible. I think I'd want to be a great basketball player during the season. I think it'd be amazing to dunk, and then you'd get laid. Kevin Durant when he is playing the Knicks. Favorite pop song growing up? Does Sonic Youth's album "Daydream Nation" count? "Teen Age Riot"? I would say "Shout" by Tears for Fears.

Age of first kiss. It's youngish, I think. I think I was in fifth or sixth grade. Then there was a long drop after that. I was the man in elementary school, but then I went to a different school, and it took a long time.