Mississippi Grind

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; at a bar hours later, Gerry sees Curtis and returns the favor, leading to a night of heavy drinking.

After an unsuccessful real estate showing, Gerry goes to a dog track with Curtis. They win a large bet, which Gerry gambles away. At a bar, they drunkenly attempt to bet $1,000 on a game of pool and are kicked out. Curtis explains to Gerry that "Machu Picchu time" is approaching – 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 River culminating in a New Orleans poker game with a $25,000 buy-in. Curtis agrees, spotting Gerry $2,000. Before hitting the road, Gerry steals the petty cash from his office.

They arrive in St. Louis, where 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. He lies to Curtis that he won $7,000, and asks to go to Little Rock to see his ex-wife Dorothy and estranged daughter. Gerry finds his daughter is at school; Dorothy catches him trying to steal money, and asks him to leave.

Curtis and Gerry visit a casino in Tunica, Mississippi, where Curtis' VIP card is rejected; asking Gerry for money, Curtis discovers his lie. Disappointed in him, 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 and go to a horse race, losing almost all their money 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 Curtis. Gerry gets punched on the nose. Curtis gets thumped after a pickup basketball game. He offers strangers $100 for a game and 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 his substantial 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 Simone calls Curtis, who proclaims 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. Gerry wants to pay off his debts, get a car and a white suit and do something nice for his daughter.

In the morning, Curtis finds Gerry has gone, leaving Curtis’ 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, Curtis replies, "Peru" and offers to take her with him.

In the final scene, Gerry re-purchases 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 tape describes the tell of a confident player (sitting back, relaxed shoulders), Gerry relaxes his shoulders as an American flag can be seen reflected upside down in the windshield.

• Ryan Reynolds as Curtis Vaughn
• Ben Mendelsohn as Gerry
• Sienna Miller as Simone
• Analeigh Tipton as Vanessa
• Alfre Woodard as Sam
• Jayson Warner Smith as Clifford
• Robin Weigert as Dorothy
• Marshall Chapman as Cherry
• Jane McNeill as Kate
• Indigo as Dora
• James Toback as Tony Roundtree
• Jason Shaffette as Chuck

On August 15, 2012, Jake Gyllenhaal was in talks to join Anna Boden and Ryan Fleck on their gambling project; the duo would direct the film Mississippi Grind penned by themselves.[5] On January 7, 2013, Ben Mendelsohn joined the cast of the film to star opposite Gyllenhaal.[6] On February 1, 2013, it was announced that Panorama Media would produce the road trip drama Mississippi Grind, with Electric City Entertainment producing.[7] On June 27, 2013, Ryan Reynolds joined the cast of the film to play the lead as a gambler, replacing Gyllenhaal in the cast.[8] On November 6, 2013, Sienna Miller agreed to a starring role in the film alongside Reynolds and Mendelsohn, with production to start in January 2014 in New Orleans.[9] On January 8, 2014, there was a casting call for extras to film some scenes at Mobile Greyhound Park in Mobile.[10] On January 27, 2014, Analeigh Tipton signed on to join the film.[11]

The film had its world premiere at the Sundance Film Festival on January 24, 2015.[15] On January 28, 2015, A24 Films and DirecTV Cinema had acquired distribution rights to the film.[16] The film went onto premiere at the Karlovy Vary International Film Festival on July 4, 2015.[17] and Melbourne International Film Festival on August 1, 2015.[18] The film was released through DirecTV Cinema on August 13, 2015, before being released in a limited release on September 25, 2015. It was scheduled to be released on video on demand on October 13, 2015.[19][20] It was selected to be screened in the Gala Presentations section of the 2015 Toronto International Film Festival.[21]

• Mississippi Grind at IMDb