Mississippi Grind is a 2015 American comedy-drama film written and directed by Anna Boden and Ryan Fleck. It stars Ben Mendelsohn, Ryan Reynolds, Sienna Miller, Lio Tipton, Alfre Woodard and Robin Weigert. The film was released by A24 on September 25, 2015.
Plot
Gerry, a struggling gambler and real estate agent, meets Curtis, an itinerant younger gambler, at a casino in Dubuque, Iowa. Curtis buys Gerry a drink; hours later, Gerry returns the favor, leading to a night of heavy drinking.
After an unsuccessful real estate showing, at the dog track, Gerry and Curtis win big, but Gerry gambles it away. At a bar, they drunkenly attempt to bet $1,000 on a game of pool and are kicked out. Curtis tells Gerry it's almost "Machu Picchu time" – a phrase he uses whenever he leaves town. In the parking lot, Gerry is stabbed in an attempted mugging.
Gerry's loan shark, Sam, threatens him to pay the money he owes her. Running into Curtis, Gerry proposes a gambling trip down the Mississippi, culminating in a New Orleans poker game with a $25,000 buy-in. The game is being held by Curtis' former acquaintance, Tony Roundtree. He agrees, spotting Gerry $2,000. Before hitting the road, Gerry steals the petty cash from his office.
Arriving in St. Louis, Curtis reunites with Simone, a prostitute. After Gerry's successful poker session on a riverboat casino, he and Curtis spend the night with Simone and fellow prostitute Vanessa. While Gerry bonds with Vanessa, Simone reminds Curtis she has been taken advantage of by a gambler before, and remains unwilling to run away with him.
In Memphis, Gerry plays well at Texas Hold 'em but loses everything on the final "river" card. Lying to Curtis that he won $7,000, he asks to go to Little Rock to see his ex Dorothy and estranged daughter, Wendy. Wendy is at school; when Dorothy catches him stealing money, she asks him to leave.
Curtis and Gerry go to the Tunica, Mississippi casino, where Curtis' VIP card is rejected; asking Gerry for money, he discovers his lie. Disappointed, Curtis provokes strangers in the bathroom into assaulting Gerry, who later admits to his problems with money, and his belief that Curtis is his good luck charm.
Reaching New Orleans, they sell Gerry's car, going to a horse race, and lose almost everything on a longshot. Curtis splits their funds equally, giving Gerry $100 for a bus ticket home. But then he collects his winnings, $5000, having bet on a different horse instead. Gerry fails to talk his way into the high-stakes poker game using Curtis as his in, as Tony clearly dislikes him and gets punched in the nose. Curtis gets thumped after a pickup basketball game. Offering strangers $100 for a game, he expects them to rob him when he loses and says he has no money; to his surprise they just take the $100. Curtis then visits his mother Cherry, a cabaret performer, leaving her most of his winnings.
At a casino, Gerry bets the last of his money first on a slot machine then on roulette and wins. Curtis arrives at Gerry's blackjack table and loses his remaining money, but Gerry shares his chips. Their winnings continue to grow as they play craps, and Curtis calls Simone, proclaiming his love for her. Convinced they cannot lose, Gerry and Curtis bet their entire $285,000.
Over an expensive dinner, Gerry and Curtis discuss their plans, having won a half-million dollars. Curtis wants a white Cadillac but when asked repeatedly all Gerry can come up with is he wants to do something nice for his daughter.
In the morning, Curtis finds Gerry has gone, leaving his half of the money with a note: "It's Machu Picchu time". Curtis flirts with the hotel clerk; asked if he is going anywhere special, he replies, "Peru", offering to take her with him.
In the final scene, Gerry buys back his car from the dealer he sold it to, telling the man he "got lucky." Sitting in his own car again, he turns it on and hears the gambling tips CD he left in the stereo. As the CD describes the mark of a confident player (sitting back, relaxed shoulders), Gerry's slouching posture transforms into a confident one and an American flag can be seen reflected upside down in the windshield.