Gerry (Ben Mendelsohn), a perpetual gambler facing financial hardship, enters a casino in Dubuque, Iowa, where he meets Curtis (Ryan Reynolds), a younger traveling gambler, while playing Texas hold 'em. Curtis wins a hand and buys Gerry a drink, and a friendship begins. Hours later, Gerry sees Curtis playing darts at a bar and buys him a drink. Curtis explains his strategy for playing cards well, in that he has no emotional investment in the outcome of the game. The two drink heavily.
After an unsuccessful real estate showing the next morning, Gerry goes to a dog track with Curtis. They initially win a large amount of money, but Gerry is unwilling to walk away, and he ultimately gambles away their winnings. Afterward, they drink at a bar, where they attempt to bet $1,000 on a game of pool. The men at the pool table are not interested and they force Curtis and Gerry to leave the bar. In the parking lot, Curtis explains to Gerry that “Machu Picchu Time” is approaching, which is the phrase he uses whenever he leaves town, implying that he is heading to Machu Picchu in Peru, which he has yet to actually visit. Gerry is then threatened by a man, who had overheard the attempted $1,000 bet in the bar, not knowing that Gerry was bluffing. The man stabs Gerry, leaving a mild cut in the abdomen.
The next morning, Gerry meets Sam (Alfre Woodard) in a restaurant, where Sam demands that Gerry pay her the money he owes, which he does not have. She wants the money the following day, or else she will call upon her friend Tim to “pay [Gerry] a visit.” Gerry then runs into Curtis at a bar, where he proposes a trip down the Mississippi River, where they will gamble at several major cities, and ultimately play at a poker game in New Orleans with a $25,000 buy-in. Curtis agrees to spot Gerry $2,000 for gambling, provided that Gerry drives his car.
The two arrive in St. Louis, where they meet prostitutes Simone (Sienna Miller) and Vanessa (Analeigh Tipton). After Gerry has a very successful poker session on a riverboat casino, Gerry and Curtis spend time in St. Louis with Simone and Vanessa. Simone warns Curtis of previous times he has trusted a fellow gambler and ended up being deceived. In Memphis, Gerry is playing very well at the poker table, when he loses everything on the final “river” card of a Texas Hold ‘em game. Gerry then lies to Curtis, saying that he won $20,000 and is inspired to go to Little Rock to make amends with his ex-wife. Curtis agrees to come along. Gerry is welcomed into his ex-wife’s house, where he attempts to steal her money from the sock drawer. She catches him and tells him to leave.
Curtis and Gerry then go to Tunica, Mississippi, where Curtis’ players card is rejected when he uses it to pay for his hotel room. After asking Gerry for some money for the hotel room, Curtis discovers that Gerry had lied to him, and that he lost all of his money in Memphis. Curtis tells Gerry that if he continues on this path, it will not end well for him. In the restroom, Curtis agitates some younger men, and when they see that Curtis has left the bathroom, they direct their anger towards Gerry and beat him.
The two go to a horse race in New Orleans. After selling Gerry’s car, they agree to bet on a horse, but Curtis secretly bets on a different horse. When Curtis’ horse wins, he does not tell Gerry, and Gerry assumes they are out of money. Having heard of Tony Roundtree (James Toback) from Curtis, Gerry goes to Tony’s house for a poker game, but admits he does not have enough money to play. Tony hits him and throws him out. Curtis loses a pickup basketball game and gets beaten up by the men he was playing. Curtis then goes to a cabaret club, where he buys a drink, and leaves the rest of his money with a singer, who is also his mother (Marshall Chapman). Gerry goes to a casino, where he places the last of his money on “00” on theroulette table and he wins. He then begins playing blackjack, where Curtis shows up at the table, out of money. Gerry is playing well, and shares his money with Curtis. After several hours of playing craps, the two have amassed a huge fortune, totaling $285,000. Curtis calls Simone and proclaims his love for her. Convinced that they cannot lose, Curtis and Gerry place all their money on the field line. Gerry rolls the dice, and the outcome is unclear.
Curtis and Gerry are shown eating lobster and steak, discussing their win of a half of a million dollars. They are comped a suite, where they keep their cash in a large safe. The next morning, Curtis finds that Gerry has left. In the safe, he sees his half of the money, along with a note from Gerry, saying “Macchu Piccu time.” Curtis decides to travel to Peru, while Gerry re-purchases the car he sold in order to have the money for the final run at the casino, and when he turns on the car he hears the gambling tips CD he left in the stereo describing what true confidence in a person looks like, and with this he smiles.
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