The Writing-Directing Duo of Anna Boden and Ryan Fleck Tell Us About the Gamble Behind ‘Mississippi Grind’

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Since their debut feature, 2006’s Half Nelson, the writing-directing duo of  Anna Boden and Ryan Fleck have crafted a number of films about smart, capable people who undermine themselves when it matters most. This particular theme is present in their other films – 2008’s Sugar, 2010’s It’s Kind of a Funny Story, and Mississippi Grind, their new film about gamblers starring Ryan Reynolds and Ben Mendelsohn. Perhaps the best way to describe their characters would be tragically human, and both Reynolds and Mendelsohn play characters that fit that particular description.

“I think that, for whatever reason, I wish we knew the answer, could’ve saved some money on therapy, is that we’re drawn to those people in the movies that we both enjoy watching and making,” say Ryan Fleck on their flawed naturalistic characters. “Like something about messy, complicated people who you like and you root for but just one wrong decision away from going down the rabbit hole. And I think there’s something about those people that we love.“

“People who you root for despite yourself,” Anna Boden adds. “People who you root for even though they make it very hard to keep rooting for them.”

What helps Mississippi Grind stand out apart from other roles in the filmography of Ryan Reynolds is the deft balance between his charming snark and a certain sense that his character is wounded, something that isn’t too prevalent in the actor’s other roles.

“I think that the character and the writing gives him the space to explore that, but it’s him. It’s all him,” Boden says of their leading man. “He really is a wonderful actor and maybe hasn’t always had the space to explore those things in the roles he’s played before. It’s interesting, how you described how he normally is is a little bit how Curtis tries to present himself to the world. This drifter that has no past and doesn’t care about the future and living in the moment care free, and that’s what Gerry is drawn to in Curtis. So it’s like a really fitting role for Ryan Reynolds. But at the end of the day, we’re not interested in somebody who is actually like that, we’re interested in somebody who is using that image to hide something that’s sad and vulnerable and lonely and messed-up like the rest of us.”

But that sense that there’s something wrong with Reynold’s character is noticeable in his very first scene. Boden offers an explanation for that, “We started shooting at 11:30pm and were going to 11:30am so there was actually something there. His brain was only half there.”

“Running on fumes,” Fleck adds.

As for Reynolds’ co-star Ben Mendelsohn, the duo has nothing but praise to heap upon the actor. When asked if there’s anything that Mendelsohn can’t do, Boden says, “No. I can’t think of it. Maybe if there was a role for a five-year-old girl, he might not be able to sell that.”

“He’s pretty transformative,” Fleck counters. “I don’t know, Anna. Don’t sell the man short.”

“Both of those guys, Ben Mendhelson and Ryan Reynolds, we would work with – we just want to work with them on every project,” Boden adds to the praises of their actors.

“He’s terrific,” Fleck adds. “I don’t know what to say.”

“He’s a mad genius,” says Boden.


When explaining what drew them to tell the tale of gamblers, Fleck looks at the romanticism of the gambler. “There’s always been something romantic about poker, a poker room at the bar. An old saloon. The old west,” the director says. “McCabe & Mrs. Miller starts with a poker scene. There’s just something about it that feels like frontiers-y.

“We weren’t poker players,” he continues. “We don’t know anything about it. On film and those characters are just people that we gravitate towards. We said, ‘You know what, let’s learn how to play poker. Let’s make a movie about gamblers.’ So it was a learning experience for us. We hit the road. We made that road trip, the same one the guys make in the movie. We stopped in casinos. Basically, we did an online tutorial before this, so we had zero experience playing poker with strangers. And we bought into a poker tournament in Tunica, Mississippi. They assigned us to a table, and it was like $60 each to buy-in. And here I am sitting at a poker table. I had no fucking clue what I’m doing, and everyone knew it in about 30 seconds. That was a really scary feeling. Like, how do I fool these guys into thinking I know what I’m doing? And there was no way around it. As time went on we learned more and more about how to play. That same day that I made a fool of myself with these guys, Anna managed to last in the tournament for hours. “

“Because I played conservatively,” Boden counters to Fleck. “Because what’s the point of being there unless I can sit around table and meet the people that live in this space? And so I spent hours just chit-chatting and playing with this random collection of people who I’d never have met otherwise. It was really important to the movie. In fact, one of the lines – something that somebody said at that table informed the entire rainbow theme in the movie. He said, kind of to himself and to the rest of the table, ‘I drove to the end of a rainbow once, there wasn’t nothing there, it just faded out into the trees.’ It seemed so strange, such a weird thing to say, and yet so pertinent and about what this journey was for these guy and about what gambling is – searching for that pot of gold at the end of a rainbow and that question of ‘What’s there when you get there?’ And we ended up weaving it all the way though our movie.”

Playing into the hard luck aspect of Mississippi Grind is the wonderful soundtrack that features a blend of country, soul, and the blues. But don’t expect a history lesson on these genres from the filmmakers. “We didn’t know much about any of those genres of music,” Fleck explains the genesis of the soundtrack. “Thankfully, Anna has a friend who’s just kind of like the biggest music nerd. We’re like, ‘Hey, can you put together a list of some blues for us?’ And he sent us a playlist of thousands of songs. We thought he was gonna give us 20 or something, and we just sifted through it and had the best time listening to these gems. I don’t know enough about the music to know how known it is, but it just felt like we were discovering something secret. And it just felt neat. It was just really cool to hear this music that isn’t your standard Top 40 pop movie soundtrack. Thankfully, we were able to get most of everything we wanted in the movie.”


“There’s the gambling part of the movie where they go to dog tracks, horse tracks, and off track betting parlors, and casinos and poker rooms,” he continues “But they also, in the tapestry of that, they go to a blues saloon. There’s like this 85-year-old blues player named Leo Welch who’s like jamming in the movie and Ryan Reynolds’ character is dancing at one of his concerts, and it’s just this underground blues club in Memphis and it’s just like, ‘Yeah!’”

Mississippi Grind, which opens in New York on September 25th and Los Angeles on October 2nd before expanding into other cities, has been available to rent on DirecTV for a few weeks now, part of new partnership between A24 and the satellite provider. “It’s a new model,” Fleck says of the partnership. “A24 has partnered with them, so they did the Jake Gyllenhaal movie Enemy. I think Slow West did as well. I’m not sure. It’s new.

“We’re trying to embrace the new model,” says Bowden.

“It sounds strange when you first hear about it,” Fleck adds. “When they approached us at Sundance and were like, ‘Here’s what we’re going to do with the movie.’ And your like, ‘Wait, what?’”

“It’s a way to get it out to more people,” Boden says of the constantly changing distribution models. “Not a lot of people in New York have DirecTV. I’m not sure about L.A. But a lot of people in the rest of the country do, a lot of people who might not have it playing in a theater near them. I guess we’re trying to embrace the new models and opportunities. Of course, you want the real movie-going fans to go out and see it on a big screen, in the way that we always intend for our movies to be seen. But, you know, fewer and fewer people are going out and doing that these days, so we have to kind of acknowledge that we want as many people to see it as possible.”

Mississippi Grind is the filmmaking duo’s first film in five years. Now that the film is gearing up for its theatrical release, what do the filmmakers have lined up on the horizon? “What we like about the filmmaking process are the stages,” Fleck says of the duo’s future plans. “We tend to try to be doing multiple stages at once, but we’re a little slow. So right now we’re starting the writing process again, now that we’re putting the movie out there. We’re a ways off from getting something going again. Hopefully, not five years again.”

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