There are some people who just can’t help but roll the dice. No matter how far ahead or behind they are, they just need to have one more go at the “big win”. And as any longtime gambler knows, the win is incomparable elation. Though in the long run, this mentality always loses. Statically, a lifetime of gambling is bankrupting. It leads to broken relationships, distrust and disquieting desperation. With some, the influence to bet it all becomes a certifiable addiction the likes of crack or caffeine or Lost. Those able to delude themselves blindly forgo the notion that the odds are never in their favor. The house always wins.

Gerry (Ben Mendelsohn) is one of these people. Though affable and a confirmed good time, even Gerry knows he’s not a good guy, and he’s willing to tell you the truth of it. A lifetime of horse tracks, slot machines, poker tables, greyhound races and blackjack has left him penniless, alone and in debt to most he knows. He hasn’t spoken with his daughter in years and his ex-wife wants nothing to do with his devious, sock-drawer-thieving ways. Even while Gerry attempts to portray a glass-is-half-full image, it’s understoof that his cup hath runneth dry.

Enter Curtis (Ryan Reynolds), a shamrock of a drifter with an immeasurable penchant for knowing when to hold ’em and when to fold ’em. At a small-time Texas Hold ‘Em tourney, the implacable Curtis squares off against Gerry, throwing a crux to Gerry’s audiobook-trained read on rival players. Woodfords are ordered and shared and Curtis’ hard-working mouth extends just enough outsider anecdotes to win over the small-town folk, most especially Gerry. A night of darts cement their favor for one another. A post-Woodford stabbing proves that sans Curtis, Gerry is a man shit out of luck.

In a last ditch effort to reconcile his outstanding debts before the squeeze becomes too much to bear, Gerry teams up with his new good luck charm Curtis on a hunt for a big score in New Orleans. What follows is a Tom Sawyer-nodding tramp down the Mississippi in which we can’t quite place who is Tom and who is Jim. As their odd-couple road trip ambles down the banks of the surging river, they stop off at various intersections – here a upscale whorehouse housing an old flame, there a familiar casino where Curtis once held VIP status.

Each terminal casts glimpses into the perennial migrant that is Curtis, without giving him away before the final card is dealt. As Curtis remains a bit of a mystery throughout – providing a curious counterpart to Gerry’s transparent distress – he becomes a bit of a noble savage of the open road. But Reynolds handles the character better than most, injecting Curtis with just the right amount of playboy charm without trotting into the obnoxious snark that too often characterizes him as an actor.

As the duo near their final destination, Gerry’s unconscionable side sees the light of day and Mendelsohn is able to work the character into empathic though despicable territory. With a losing streak this hot, we pity Gerry rather than cheer him to a win because we know that one win inevitably leads to five losses.

Strong chemistry between Mendelsohn and Reynolds ease the more predictable elements from taking hold and directors Anna Boden and Ryan Fleck‘s ability to slam the occasional magical surrealism into his pragmatic sentiment makes Mississippi Grind a well-played victory, if not a chip-sweeping royal flush.