Bitterly funny gambling comedy Mississippi Grind transcends its generic lovable-losers-on-a-bender plot by foregrounding exceptionally well-developed skid-row protagonists and weirdly charming dive-bar ambiance. Co-writer/-director team Anna Boden and Ryan Fleck (Half Nelson, It's Kind of a Funny Story) are most interested in the low thrum of white noise that innocuously fills racetracks; the hungry stares of poker table hustlers; and the bar-side bullshit sessions that characterize desperate gambling buddies Gerry (Bloodline's Ben Mendelsohn) and Curtis (Ryan Reynolds).
You can tell what will happen to Gerry and Curtis as soon as Gerry latches onto Curtis as his lucky-charm companion and commits to driving with him from Dubuque to New Orleans for a big score. But it's easy to get lost along the way thanks to an abundance of wryly funny barfly banter: Curtis warns Gerry that trusting a greyhound named Rollin' Roosevelt was a mistake — you "never bet on a dog named after a disabled president."
Boden and Fleck are also patient enough not to overemphasize the pathetic nature of Gerry and Curtis's addictions to gambling, drinking, and bullshitting. The scene where Curtis fails to seduce jilted lover Simone (Sienna Miller) hurts so good because she initially seems to buy his romantic spiel. But when Simone verbally splashes cold water on Curtis, and asks him if she should pack condoms "in case I have to work, to cover my expenses," you realize just how suckered you are by Boden and Fleck's slow-burn character study.