It's 2003, and Huck Cheever (ERIC BANA) is an expert professional gambler, able to read and bluff most anyone. However, his main problem -- which constantly leaves him broke -- is that he lets his ego get in the way and prefers to steamroll over his opponents, a tactic that obviously doesn't always work. It turns out his biggest external nemesis is his own father, L.C. Cheever (ROBERT DUVALL), another compulsive but much more successful professional gambler who's twice won the World Series of Poker tournament.
Needing $10,000 to enter this year's challenge, Huck can't bring himself to ask his estranged father for the entry fee, and he isn't sure if Vegas local Roy Durucher (CHARLES MARTIN SMITH) will loan him the money. Accordingly, he hocks his roommate's digital camera, takes the money, and builds up his winnings. Unfortunately, his style of play repeatedly undermines his efforts, once again leaving him without cash. Enter Billie Offer (DREW BARRYMORE), a recent transplant from California who's arrived in town and landed a job singing in a local club. Her sister, Suzanne (DEBRA MESSING), knows Huck all too well, but despite her warnings, Billie finds herself drawn to him.
Of course, he just sees her as another possible source of betting money, all of which puts a strain on their budding relationship. With the clock counting down toward the tournament's entry deadline, Huck does what he must to get in, with everyone hoping perhaps he's learned a thing or two and thus might change his ways.