The movie opens with Gerry (Mendelsohn) listening to a recording of poker 'tells', then entering a poker tournament at a casino. He's soon joined by Curtis (Reynolds), who wins the first hand big and makes friendly overtures to Gerry. Later, Gerry enters a bar and encounters Curtis and they proceed to get drunk together and begin a friendship. Curtis indicates he's heading to New Orleans (NO) the next day. Gerry awakens on Curtis's girlfriends couch and receives a call from Curtis, who convinces Gerry to meet him at a dog track, where they win big. Curtis wants to leave but Gerry gets him to stay and Gerry loses his winnings. Later at a bar Curtis seems to relate a story about quitting gambling when one is ahead, but gets Gerry to bet big on a game of pool. Gerry is showing signs of being a compulsive gamble. They split up and Gerry is stabbed - superficially - by a mugger. The next morning Gerry meets Sam (Woodard) who seems to be trying to collect a large amount of money Gerry owes her (or who she represents). Sam threatens Gerry, saying she'd send a "Tim", which seems to scare Gerry. That night in the same bar as the previous day, Gerry receives a call from Curtis, who states he won some tickets, which keeps him in town. Gerry is apparently superstitious and takes Curtis's presence as good luck. Gerry convinces Curtis to stake him on a trip from St. Louis to NO which he's convinced will allow him to earn the $25,000 entrance fee for the tournament Curtis says he's heading to NO for. Curtis agrees. They drive to a riverboat in St. Louis, where Curtis conveniently knows one of the waitresses, whom he has a relationship with, though he hasn't seen her in 7 months. Gerry wins big at the table. Gerry attempts to place phone bets which the callers refuse because of his debts. They drive to Memphis, Curtis stopping Gerry from listening to the poker tells recording. They go to a dog track in West Memphis (Arkansas). Later Curtis enjoys the nightlife on Bealse while Gerry loses at a poker game. Gerry receives a threatening text from Tim and later tells Curtis he won 7,000 (a lie). Gerry says if he would have won bigger he would go to Little Rock to see his ex-wife. Curtis obligingly suggests they go there anyway. Gerry's visit doesn't go well and his wife catches him trying to steal money while ostensibly going to the bathroom. That night they stop at a casino in Tunica, MS. Curtis ask Gerry for some of the money to pay for a room and Gerry throws a tantrum. Curtis figures out from this that Gerry lost the money in Memphis. Curtis gets Gerry beat up by some punks before intervening. They head toward NO, where they sell/pawn all their belongings, Gerry convincing Curtis to place this money on a long shot at a horse racetrack only to lose. They split up. Curtis has secretly bet on the horse he preferred and wins 5,000. He, inexplicably, purposefully gets himself beaten up and then goes to a bar and meets his mother - a lounge singer, leaving her the rest of his money! Gerry meanwhile tries to talk himself into the NO game, only to get punched for his efforts. He winds up at a casino and starts a win streak. Curtis arrives, and encourages Gerry to bet it all. He does and they win half a million! That night Gerry leaves with half the money, not telling Curtis.