In just a handful of movies including ‘Half Nelson’ and ‘Sugar’, co-writers/directors Anna Boden and Ryan Fleck have established themselves as filmmakers dedicated to tales of fumbling outsiders. They approach these characters with care and love, but aren’t bound to presenting them as heroes or forcing their broken people into happy endings. So, it only makes sense that they would make a movie about degenerate gamblers and it would turn out to be the best film on the subject since the 1970s gambling masterpieces ‘California Split’ and ‘The Gambler’.
(It’s also no coincidence that James Toback, the writer/director of the autobiographical ‘The Gambler’, made a cameo in this movie rather than the remake of his own.)
Ben Mendelsohn stars as Gerry, a man who was born to lose, the type of person who shouldn’t be drawn to gambling yet inevitably is. He’s deep in debt to pretty much everyone he knows and keeps digging a deeper hole convinced that he can get out of it. One day at a poker table, Curtis (Ryan Reynolds) walks in as a lost gambling soul of a different sort, and the two bond over hard luck stories and delicious bourbon.
Curtis has no home and wanders around seemingly aimlessly. He plans to take a trip to New Orleans for a big game, and since Gerry considers the guy good luck, he talks Curtis into letting him tag along and hitting all the legal and illegal low-level gambling spots along the way. At first, they win big and have a sweet night with a pair of prostitutes, one of whom (Sienna Miller) Curtis enjoys an on again/off again love affair with. Everything seems great until it isn’t. As is the gambling way.
You have to give Boden and Fleck credit for being willing to base an entire film around a character with as self-destructive a core as the broken man Mendelsohn plays here. He has a soft heart, but his addiction makes him do terrible things that he’s punished for at every turn. It’s often tough to watch him set himself up for another failure, but it’s also heartbreakingly compelling.
Reynolds initially seems like a brighter light. He’s playing a variation of the sarcastic charmer that made him a star. The character is defined by philosophies he constantly spouts off like, “I don’t care when I lose” or “The journey is the destination.” As the film wears on, it’s clear that he also doesn’t care when he wins and that he’s terrified to settle into anything resembling home, traits that lead to their own brand of tragedy.
Boden and Fleck’s rambling study of these two broken men is fascinating, filled with bursts of character comedy (like Gerry insistence on listening to a self-help poker CD rather than music as they drive) and harsh truths that the cameras linger on to the point of discomfort. The two actors are remarkable, with Mendelsohn finding the heart in someone who can’t help but destroy everyone around him and Reynolds finding the tragic core in his smiling persona. The filmmakers also find a rotted-out side of America to shoot that suits their lovably deadbeat world. All the days seem overcast and the road trip defined by tableau images of crumbling monuments to Americana. It’s a side of life rarely seen in film because it’s a world that most like to ignore and even those who live within it long to escape.
The filmmakers might stumble towards the end, unsure of how to end their story after hitting a number of beats that could have closed things out. But maybe that’s the point. After all, there’s rarely a satisfying button to cap off life and certainly no end to a gambling addiction, happy or otherwise.