It may be hard to find a city as celebrated in film as New York; its rich pastiche of cultures, gritty underbelly, and ability to mold to fit whatever genre a director needs makes it one of the perfect cinematic backdrops. In particular, New York often serves as the canvas on which true crime stories and mob movies play out in spectacular fashion, leaving a trail of bodies and less-than-salubrious activity in their wake. The latest in the grand canon of New York crime films is Raymond De Felitta’s Rob the Mob, based on a true story, which tells the story of Queens’ very own Bonnie and Clyde, a pair of working class Robin Hoods that stole from the rich (the Mafia) and gave to the poor (themselves). With a dynamite cast including Michael Pitt (Boardwalk Empire), Nina Arianda (Midnight in Paris), Andy Garcia (The Untouchables), Griffin Dunne (After Hours), Ray Romano (Everybody Loves Raymond), and many more, Rob the Mob covers many familiar mob movie tropes, but manages to put its own unique spin on the well-worn genre, thanks to a pervasive sense of heart that underlies the morally gray proceedings.

To take you deeper into the world of Rob the Mob, I caught up with director Raymond De Felitta to talk about how to innovate in a been-there, done-that genre, the challenges of adapting true life stories, where to get the best Italian food in New York City, and much more.

Nerdist: So the first thing I want to talk about is, these New York mob stories are sort of a classic genre at this point, so I was wondering what in particular about this trope speaks to you, and what do you think that Rob the Mob adds to it that sets it apart?

RDF: Honestly, it never had been of any interest to me to do a mob story, as much as I love the really great ones. You’ve already done it. The Godfather has done it, Goodfellas has done it, The Sopranos has done it. You’re not going to top those guys. And personally, as an Italian-American, I always sort of feel like – you know, my other work, my films City Island and Two-Family House, they were about Italian-Americans who aren’t in the mob, and I never think that those guys really get any coverage.

So I was not a person who was lining up to make a mob movie. But when I read it, what I loved about it – several different things converged. First of all, I loved the story of Tommy and Rosie, and the fact that he had this vengeance, that he had to get rid of his father’s story, and he couldn’t do it without acting out this insane plan. I also loved that I hadn’t seen this mob movie, and I thought it’s so hard to find a new wrinkle. It’s like finding a new wrinkle on a TV cop show. How do you do it? It’s been done. But every so often someone does, and you go “Wow! All right, now I’m interested again.”

This time I read it and I thought the mob are not the goofy mob, which I always find silly and boring, and they’re not really that scary or flashy. This is just the worn-out guys – that period, with [John] Gotti on trial for what’s clearly going to be the last time, you know, it’s New York in that era that’s kind of beat and broke and depressed. And they were in a sense the victims, which I thought was so peculiar. It’s like they’re the guys who are getting robbed, and they don’t know how to deal with this humiliation. So I just thought that was a great ‘in.’ And then, in a sense, not a clichéd look at your usual group of goombas. Because, enough of that – we’ve already done that. These are just guys that sit in the club and play cards and don’t really know what to do with their life anymore.

N: Exactly! That was something that really stood out, because like you said, you’re so used to seeing these mobsters in different positions of power, and they’re used to getting what they want and being able to rough their way through things. Seeing the table turned on them was really interesting. At this point, they’re just a bunch of dads and uncles trying to hold on to the crumbling remains of their empire, and just keep their heads.

RDF: Exactly. Yeah, exactly, which I just thought was really original and probably closer to the truth than what we usually get in most popular culture representations.

N: What in particular attracted you to Rosie and Tommy’s story, and what’s the challenge when you have to adapt a story like this for the big screen?

RDF: Well, one of the movies that has always inspired me as a movie maker and storyteller is Sidney Lumet’s movie Dog Day Afternoon with Al Pacino, and one of the things that I always loved about that movie is that it was a true crime, and it had all of these big, emotional journeys and themes to it. It was committed for reasons that were financial and romantic and it had elements that didn’t work. It was a fiasco. But it also really wasn’t on the radar of anyone for very long. That crime came and went on the news in a couple of days. And in a sense, I always felt like that was part of the beauty of that story. It’s not telling a story you’ve ever heard; it just happened, there it is, this lonely event out there.

So when I read the screenplay that I was first sent for Rob the Mob, I thought they really found that. Rosie and Tommy were not famous. Yes, they made the papers, but on, like, page eight, on kind of a small – and then the story went away, and then a few months later they were murdered. It was a blip on the radar of true crime, but it had all of the major emotional reasons that people commit crimes, and all of the things that we look for in really strong drama, and especially reality-based drama. So I just thought that was a huge, huge lure to me.

And then, in terms of what the challenges are, I think always the challenge when you’re dealing with real events – you want to honor them, you don’t want to twist them up, and you certainly don’t want to get them wrong, but you’re also not making a documentary, so you also have to be – you have to have one foot in the camp of the artist, the storyteller. I can’t get absolutely all of this right, and I’m not supposed to get it all right. I’m supposed to get the essence of it right, and sometimes I’m going to have to step back and say cut these scenes, I don’t need to explain this event, I may not even want to go into some of these other complexities going on around them, because that’s just going to confuse things.

So that’s always a bit of a hot topic with people when you do reality-based stories. Are you cheating if you don’t tell exactly what happened, or if you add in a character who didn’t exist? I just don’t think you can go there. I think you’re ultimately taking care of the story, not every true event around it, and along as the essence of the story is preserved and hopefully enhanced by dramatizing it, that’s what you’re there to do.

N: You were talking about how they were just kind of a blip on the radar, and you kind of get that sense, even in the film. It’s so heartbreaking when Rosie is talking to Ray Romano’s character, because you can tell they just really want to be known for something, and knowing what happens to them, it was a real gut-punch. 

RDF: Yeah. Well, they’re so good in that scene too. Nina’s so terrific, and what I think that she really got about Rosie was the combination of – it’s not really stupidity at work at all, it’s pride. She finally sees Tommy, who she’s always had all the belief in the world in, he’s actually pulled this thing off. She wants to share it. She wants people to finally know that she was right – Tommy’s a genius! And yet, of course, she buys into the idea that they’re never going to get bothered by anyone.

N: You pulled together a really terrific cast for this film. When I saw Ray Romano and Griffin Dunne and Michael Pitt and Nina [Arianda] – it was just very impressive. What attracted you to this group of performers, and who surprised you the most during the filming process?

RDF: Well, a lot of what I was trying to do in the casting process was create both excellent actors who were going to bring reality and truth to it, but also I liked the idea of using actors who you might associate with other New York crime movies, just so it felt like – I always think a sort of meta-film is going on. Like, oh, OK, for a second, I’m in Once Upon a Time in America, because Burt Young is here. Now I’m in Raging Bull for a minute – there’s Cathy [Moriarty]. So I like that idea of filling it out with really iconic crime movie faces.

But I’ll tell you who – I wouldn’t say surprised me the most, but who really impressed me the most – I wanted Burt Young. I’ve always admired him. I’ve always thought he was a fascinating actor, and a very curious individual, and he’s hard to get to, and he doesn’t really want to do much. You’ve got to kind of – he’s got to get to know you. And I went there, I went the distance, I went and met him, Michael Pitt and I went and met him. And he said, “There’s not a lot for me to do here. It’s really one scene.” And I said, “Yeah, but it’s really important, because you’re the guy – you end up, your whole life goes away with this one robbery, and you give up the list. And the guy realizes that after years of carrying the paper around, you’ve fucked up and it’s all,” you know.

And he bought that, and he came and we shot the scene, and when we got to the end of the scene, he said, “Let me just do a little something for you.” And so much pain, and so much confusion and sadness came over his face, and it suddenly kicked everything up such a big notch. It made that story point, and it was just an act of pantomime on Burt’s part. It was just watching his face emote. And that, to me, was just an amazing kind of moment – lesson, I guess you would say, in what an actor can do. He took what I needed – he understood what that guy did, and just by experiencing it and being open with it and wandering a way out, and just devoting a little, it went from a point that you understood on the page, to a much more impressive emotional and understandable thing that he had.

N: Yeah, that was definitely one of the most affecting scenes in the film. And it’s so unexpected, because you’ve got this young guy with a sub-machine gun, and three old fogeys just sitting around playing cards in the club!

RDF: [laughs] Yeah. Yeah, it was a fun scene to shoot, too. All three of them were great.

N: I have to say this film gave me a powerful hunger for Italian food. 

RDF: Yeah, I know – me too, unfortunately! It’s one of the few films that I didn’t lose weight on.

N: [laughs] Well, hopefully it was a tasty process. What is your favorite Italian restaurant, and/or dish?

RDF: In Manhattan?

N: Yeah, let’s say in Manhattan, given the film’s locale.

RDF: You know, it’s funny – the ones that I really prize are – they’re not the ‘foodie’ Italian places. They’re the neighborhood. In the West Village, where I lived for many years, there’s two that I’ve always loved: Gene’s [Restaurant] on West 11th, and Volare on West 4th. And each time I go I think I’m going to try something else, but in each place I always end up getting – I love veal stuffed with prosciutto and ham. That’s just it – that, and a little pasta on the side, and four or five bottles of wine, and I’m happy!

N: I understand you have a background as a jazz pianist, which I think is awesome. I’m curious if that musical or lyrical sensibility influences how you approach film making?

RDF: Yeah, I guess it does. I’ve played literally since I was a kid. Music’s been a part of my life forever. I can’t edit a film without immediately trying to score it. Since I don’t score my own films – before Rob the Mob, I would always temp-score something while we’re editing, because I just don’t know how film and music are separate. They have to be married. I guess the thing with jazz, if I were to make any kind of comparison – and this might feel a little wobbly, but I play jazz, I don’t play classical music, so I don’t rehearse – I’m never trying to get it right, I’m trying to get feeling out of what I do as a musician.

The longer I work with actors, the more, for me, that’s the key for working with actors. I don’t want them to get something right, I don’t want them to feel like they have to get something right. I want them to get in the moment and behave. And so I love improvising. I love letting the actors have that space, and I guess it’s really in that sense, really-and I feel comfortable with it. I don’t feel like anything unruly is happening, because I think as a musician, as a jazz musician, that’s what we do. We give each other some space, and we try to make something emotional happen.

N: Yeah, exactly. I think that’s a smart way to approach it. Obviously, you want to have a strong foundation with the script, but you also want to give yourselves a chance to explore.

RDF: That’s why good jazz usually picks a great song, and then you can play through the chords and you can let it go.

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Rob the Mob is in theaters now.