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Toronto: Even ‘Mississippi Grind’ Filmmakers Ryan Fleck and Anna Boden Were Blown Away By Ben Mendelsohn

Toronto: Even 'Mississippi Grind' Filmmakers Ryan Fleck and Anna Boden Were Blown Away By Ben Mendelsohn

READ MORE: Watch: Ben Mendelsohn and Ryan Reynolds Wage a Risky Gamble in ‘Mississippi Grind’ Trailer

Filmmaking partners Ryan Fleck and Anna Boden have always displayed a knack for casting, from the star power of their first feature “Half Nelson” (which earned leading man Ryan Gosling an Oscar nomination) to their discovery of young Keir Gilchrist for “It’s Kind of a Funny Story.” In their latest film, Fleck and Boden employ their most recognizable cast yet, including Ryan Reynolds, Ben Mendelsohn, Alfre Woodard, Sienna Miller and Analeigh Tipton, a big ensemble that are joined together in service to a deceptively simple story about two strangers — both con men, in their own ways — who attempt to cash in on one last big score.

The film centers on Mendelsohn’s permanently down-on-his-luck Gerry, a gambling obsessive who can’t seem to catch any kind of break, who finds an unexpected new pal in the smooth-talking Curtis (Reynolds). When the two hatch a plan to hit the road so that Gerry can infiltrate a high-stakes card game down in New Orleans, “Mississippi Grind” spins off into a buddy comedy/road trip drama with some real bite (and some very unexpected twists).

Fleck and Boden sat down with Indiewire on the morning of their TIFF premiere, and the filmmaking duo were happy to share insight into their process, what’s coming up for them and why their own leading man took them totally by surprise.

Were you surprised that you got into TIFF? You premiered at Sundance. Most films don’t go the Sundance-to-TIFF route.

AB: We were really hoping, because what a great way to launch the release. It’s coming out in just a week and a half now. And Ryan Reynolds, our Canadian actor, gets to come back to his home country.

RF: The homeland.

AB: The homeland. So, you know, we were really thrilled.

The release schedule on this is really interesting — you’re on DIRECTV right now, you’re going to be premiering here, and then you’re out next week. Distribution models are changing so rapidly these days.

RF: It’s all new to us.

AB: It is like a new world in terms of distribution, and the hope is that this kind of release will get it out to more people more quickly. It’s like a mixture between a more traditional platform release — we’re opening in New York and then L.A. and then a bunch of other cities — and then also the availability online for everybody else who is not going to have it in a theater near them. So you are kind of embracing this new thing with A24 and really trusting these guys that they know what they’re doing, because they’ve had such success in the past. They’ve been killing it.

RF: It’s nice for us too, because our career started with our movie “Half Nelson” and David Finkel and Daniel Katz were at ThinkFilm, and they were part of the team that put our first movie out there and basically launched our careers. So it was nice to have them be excited about the movie and sort of team up with the same team again.

You’ve been making movies as a team for awhile. How have you changed your methods since your early shorts?

RF: Well, going way back, when we were making short films, it was just the two of us. Literally, Anna had her little camcorder and I had the boom and we were making documentaries.

AB: So literally everything was shot at a low angle just because of my height.

RF: Looking up at people. [Laughs] And when it’s just the two of us, we’re making all of the decisions and we’re just collaborating with us. So, in some ways, we had a lot of control that we had to learn to give up or at least collaborate with people who are actually better at doing those things than we were.

AB: Thank God I’m not still shooting our films. [Laughs]

RF: Oh, my God, are you kidding? And I’m terrible with a boom now. I don’t even know where to aim it. So I think that was just a learning curve for us when we started making bigger movies. I mean, again, “Half Nelson” was not a big movie by any means, but we had a crew. We had a crew of 20 or 30 or 40 people, I don’t know how many it was. And that was an interesting process, just to relinquish that control and say, “Oh wow, it’s really nice to see people who are good at their jobs do them well.” What else have we learned? How else has it changed?

AB: I think that the world of making movies and how movies get made has certainly changed and evolved over the years. So we’re just trying to keep up with it and keep telling our stories in whatever way we can, by hook or by crook.

RF: We managed to shoot on film for all four movies. So I don’t know when the next one comes around, whether we’ll be able to pull that off again.

Would you like to shoot on film again?

RF: Yeah. I don’t know that it’ll be possible. We don’t have a movie lined up right now, but let’s say we did tomorrow. That means that we would be shooting six or eight months from now. I mean, I don’t know what the availability of film is going to be anymore. People are still doing it.

AB: People are still doing it. I think it’s going to still happen, but I think it’s going to become harder and harder. It would be great to continue shooting on film. Amongst other things, the mystery of not knowing exactly how it’s going to look until we see it later and having your DP and being able to trust in him that he’s the holder of how this is going to look is a beautiful mystery of filmmaking I’m loathe to look up.

RF: Yeah, it’s like a sorcerer conjuring up chemicals and creating this image that didn’t exist until it goes through the lab process. 

Your partnership has always appeared to be so fluid — how do you determine who is doing what on each project?

AB: Well, when we started out, Ryan had gone to film school and was on track to be a fiction film director. And I was doing other things in school and interested in documentary. And when we started working together, like he said, it was just the two of us kind of winging it. I think that after we made our first film “Half Nelson” together, which he directed and we co-wrote and I have a producing credit on, along with a bunch of producers, we really realized how much we work together and how organic and fluid that relationship is. Since then, we’ve pretty much co-directed all of our films and we’re trying to co-direct in television when we do television and just have that be how it is for the time being. Basically, ever since “Half Nelson,” we’ve been co-directing and it’s because we have a pretty fluid–

RF: It’s also weird, because when a movie comes out, the director gets to travel everywhere. The director gets all the attention. And I realized that wasn’t a fair representation of how we were. And it was also a really seamless transition into co-directing because our second movie, “Sugar,” was largely in Spanish and Anna’s much stronger in Spanish. So it was just boom, she’s going to help talk to the actresses, and we’re off to the races. And that worked really well, so we just kept doing it.

And when you write together, do you write side by side? Are you trading pages?

RF: It’s both. We’ll talk it out, we’ll outline some scenes, go as far as we can, separate, write separately, trade stuff, then go fine-tune it and polish it together.

You’ve had amazing luck with casting, and this film is no different. What is your approach to that side of things?

AB: I think always whenever we’re casting a movie, it’s about sitting down with somebody and feeling in them some kind of the element of who our character is. And even when we were casting non-actors for “Sugar” or in “Half Nelson” — the girl, Shareeka Epps, who plays across [Ryan] Gosling — it was about sitting down and being like, “Do I feel that you’re…”

It was no different in “Mississippi Grind.” We met Ben Mendelsohn, who had acted with Ryan Gosling in “A Place Beyond the Pines,” and that’s the first place where we’d seen him. And we’re embarrassed to say that we didn’t know that he was a famous Australian actor at the time that we saw it. We thought he was just some local guy from upstate, and we were like, “Whoa.” When Lynette Howell, who produced that film and this one as well, recommended him, we were like, “Oh, he’s a real actor?” And then we went back and looked at “Animal Kingdom” and all of his other work and we were like, “He’s not just a real actor, he’s an incredible actor.”

We sat down with him and he just exploded for us in terms of his whole personality, his charisma, the strange, volatile, odd way that his mind worked. And we were sitting across from him and looked at each other and just said this is our Gerry — without saying it. We just offered him the job on the spot, which we never do because we usually have to talk about it and weigh things. But for us it was just so immediate that this was our Gerry. And it was really similar with Ryan [Reynolds]. Of course we were more familiar with his work, but it was sitting down across from him, meeting him in person, and just knowing that Curtis was in there. 

RF: Everything that she said. She talked more about Ben, but for Ryan, we know he’s charming. We all know that side of him. But he’s just so softspoken and gentle in the room. And I know Curtis has more of a bundle of energy. But there was a complexity there that we hadn’t seen on screen in the face-to-face that we were interested in seeing on camera. And he’s also just the guy — channeling Gerry and ourselves — we didn’t want him to leave because he was just a sweet guy. We were like, “Aww, he’s so nice.” You kind of wanted to hold his hand while we were talking. You want to lean in close to him because you don’t want him to go away. And when he’s gone, you feel his absence.

We thought that was a really nice quality for this movie. When these guys aren’t together, you feel something missing, and when they are together, you’re like, it’s working.

AB: We love telling stories about characters who you root for, even though they sometimes make it really hard for you to root for them and the choices they make. And certainly for Gerry in this movie, that’s the case — Ben Mendelsohn’s character. And Ryan Reynolds is just kind of a mystery to us as well as to Gerry for the first maybe three-quarters of the movie. Slowly, his personality unravels and his history unravels and you start to see glimpses of who this guy really is. You’re not quite sure. Is it bad guys? Is it good guys?

RF: Movies like this tend to have somebody who’s scamming. It’s hinting at a history of con artists in movies. It sets that up. But we really wanted it to be real, and for us it was important that we explore a genuine friendship between strangers. That’s more of what the movie is about for us. But because of the world we’re in, where gamblers tend to be schemers, there’s an expectation that somebody’s going to hustle somebody by the end of the film. And that may or may not happen, dot dot dot.

The entire film, you’re waiting for something like that happen, because audiences are so trained to see that sort of thing in con artist movies. It’s such a pleasant surprise when that doesn’t happen.

RF: We hope so, thank you. For some people, it’s like, oh it didn’t do the thing that I thought it was going to do and there must be something wrong with the movie. But no, the movie is perfect. [Laughs]

That’s my headline right there.

RF: My movie’s perfect!

You said earlier that you don’t have anything coming up right away, but what’s going on with “Hate Mail” and “Special Topics in Calamity Physics”?

AB: “Special Topics in Calamity Physics,” years ago, before we made “It’s Kind of a Funny Story,” Miramax hired us to adapt the book. And we loved the book, too. It’s so great. We got excited about it. But shortly after we wrote it things really changed at Miramax.

RF: Miramax kind of imploded.

AB: And it’s been off our radar for a little while now.

RF: I think the rights went back to the author of the book. I don’t know what’s happening with it.

AB: But maybe we’ll look into, now that you’ve mentioned it.

RF: And then “Hate Mail” is actually interesting because it led to this movie. Because it was a big “Shortcuts” style ensemble, a “Nashville” kind of thing happening in New York. And it was a bunch of parts. And we would cast one, as we’re trying to cast another, we’d lose that actor–

AB: To some big movie. Like they’d be in “The Hunger Games” all of the sudden.

RF: Tragically, Philip Seymour Hoffman was one of those actors. And he’d gone to do another movie, and then sadly he died. But it just became so frustrating trying to navigate that — we said, you know what, let’s just make something simple. Let’s just get two actors on the road with a very small crew and get back to the roots of the kind of films that we want to make. This ended up being a little bit bigger in scope than the original conception of the film, but it came out of the frustration of trying to do something that was bigger and more ambitious, just to strip it away. Everything’s so contingent on the actors–

AB: For this kind of movie that we love to make.

RF: If it’s not a high-concept movie, if you’re not having outer space people come down and blow stuff up, then there’s a pool of 15 to 20 male actors and 10 to 15 female actors. And if you don’t get one of them, you really need to reexamine your budget and the story you’re trying to tell. It’s frustrating.

So what’s actually on the horizon?

AB: We’re always throwing around ideas and working on some writing stuff, but nothing that we can say is definitely coming up next.

RF: Yeah, we’re in the early writing stages of something, but it’s not really a thing yet.

AB: We usually have a couple of ideas and then zero in on one, but have the other one kind of hanging out. Because you never know. You might go down the road a little bit and then decide, “Ehh, it doesn’t really have legs.”

“Mississippi Grind” is currently available on DIRECTV and will open in New York City on September 25 and Los Angeles on October 2, with an On Demand release to follow on October 13. 

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