This movie features Mike McDermott (Matt Damon) trying to climb the poker ladder by beating the marks into submission and then challenging the better players when he has enough money to compete on relatively even footing. This movie was one of the first films to capture the excitement of Texas Hold 'Em poker craze and helped build its popularity. His meeting with Russian expatriate Teddy KGB (John Malkovich) shows McDermott's growth as a poker player because McDermott finds a way to win the matchup. After the shocking loss, an irate KGB collects himself and then instructs his underlings to "pay that man his money." The poker on display may not be technically sound, but it sure makes for good watchin'.
2. "The Sting" (1973)
This classic movie featured Paul Newman and Robert Redford playing two Chicago con men during the 1930s. One of the great cons takes place at the poker table, where Newman's character Henry Gondorff uses his skill at draw poker to fleece the other competitors he is playing. Those skills involve deception and he is clearly a card shark who enjoys feasting on weaker fish. A word to the wise, though; steer clear of the ill-advised "Sting" sequel.
3. "Lucky You" (2007)
Huck Cheever (Eric Bana) is a talented poker player who is capable of competing with the best poker players for long stretches, but often lets emotion overcome him at the wrong moments. With the World Series of Poker coming up, Cheever must come up with the $10,000 entry fee if he wants to have a chance–and he'll do anything he can to get it, including stealing. The story gets complicated when Cheever's detested father (Robert Duvall), also a poker player, shows up to compete. Huck's ability to hold himself together determines his fate at the poker table.
4. "The Cincinnati Kid" (1965)
This poker movie became a big hit at the time of its release because it depicted the lifestyle as the poker player as a playboy. Eric Stoner (Steve McQueen) makes his money by playing in high-stakes poker tournaments in many of the riverboats that were prevalent in the 1930s. Stoner is the quintessential 5-card stud player who can seemingly read every other player at the table during a crucial hand. When Stoner is not at the poker table, he is wooing and winning the most beautiful women he meets.
5. "Maverick" (1994)
Maverick (Mel Gibson) is a con man and a great poker player. He would rather run a good con than do just about anything else. He's at home at the poker table and he needs to come up with buy-in money to enter the winner-take-all poker tournament. He eventually teams up with Annabelle Bransford (Jodie Foster) and is able to play. James Garner, who played Maverick in the 1950s television series of the same name, is featured as Marshal Zane Cooper in this movie.
6. "A Big Hand For The Little Lady" (1966)
Meredith (Henry Fonda) and Mary (Joanne Woodward) are moving to San Antonio. As they travel across Texas, they run across a big-time poker tournament that Meredith somehow gets roped into playing. The stakes are high and more than Meredith can afford to play. Just as he reaches the tournament's climactic hands, Meredith has a heart attack and Mary has to take over if she wants to hold on to the family's money.
7. "High Roller: The Stu Ungar Story" (2003)
Stu Ungar (Michael Imperioli) was a top tournament poker player. Many considered him to be the best player ever when he won the three Main Event titles in the World Series of Poker. However, the rest of his life was out of control. It was once said about Stu that "Most man can have one, maybe two vices, and they can survive. Stu had every vice." As good a poker player as there ever was, this film examines his short life and tragic death at the hands of his many excesses.