In the early days of speaking films in Hollywood, poker could often be found in many Westerns. Poker was an exciting game played by cowboys, outlaws, and notorious gamblers or at least it was portrayed that way in the films of that era. Some notable poker films from before World War II included Three Godfathers (1936) and Sunset Strip (1939). After WWII, more regular people began playing poker as a social activity but to Hollywood, poker still remained a game that was popular among criminal elements.
Cincinnati Kid (1965)
The first poker movie that caught my attention was The Cincinnati Kid. I originally wanted to see it because I was a fan of Steve McQueen’s films. Little did I know that poker would be a central character in the film and that the infamous Edward G. Robinson acted as the villain. Taking place in New Orleans, we watch as a young card player (McQueen) gets to sit in a game against the best Five Card-Stud player in the country, Lancey Howard (Robinson). The final hand is an amazing scene technically from a film makers perspective and it's also extremely thrilling to poker fans. One of my favorite movie quotes is by Steve McQueen when he explains, "That's what it's all about, doing the wrong thing at the right time."
The movie that got me hooked on Texas Hold'em was Rounders. I played in an underground private club a few times before the film’s debut, but we only played Seven-card Stud. After the film was released, Texas Hold'em slowly began creeping up in home games and no limit Hold'em began to grow in popularity. Rounders is one of the few poker movies that can stand on it's own as a film. Every poker player I have met has seen Rounders at least once.
The storyline is compelling. Mike McDermott (Matt Damon) is a law student who loses his entire bankroll in a single hand to Teddy KGB (John Malkovich), a Russian mobster who runs a private card room in New York City. Mike quits high stakes poker and focuses on law school. He is forced out of retirement to help his best friend Worm (Ed Norton), a career criminal, who is released from prison with a huge debt hanging over his head. With Worm's life at risk, Mike is forced to have to win a lot of money in a short period of time. He sits in dozens of games all over New York City and eventually plays heads up against his nemesis Teddy KGB in the final scene of the film.
The Sting (1973)
This is one of my favorite films of all time and it won seven Academy Awards. The Sting is more about the big con at the end of the film more so than a poker movie. There is an amazing scene where Henry Gondorff (Paul Newman) plays Five Card Draw against a gangster named Doyle Lonnegan (Robert Shaw), in the back of a train bound for Chicago. Lonnegan thinks he's setting up a cold deck to cheat Henry, but Henry ends up cheating Lonnegan and wins. The results in that game sets up the final scene of the movie, where Henry and his partner Johnny Hooker (Robert Redford) fix a horse race.
Lock, Stock and Two Smoking Barrels (1998)
Guy Ritchie directed an entertaining story about of a couple of working class friends trying to hit a big score when they bankroll their mate in a high stakes game. He ends up losing when the game is fixed and has to pay back a massive debt to a local pornographer. Hijinks ensue when they decide to rob their drug-peddling neighbors.
Sylvester Stallone is "The Dean," the best player around. Stuart Townsend is a con-artist and his partners (Thandie Newton and Gabriel Byrne) are trying to take down The Dean by any means possible. Of course, there's plenty of plot twists and cameos from Melanie Griffith and Jaime Foxx.
California Split (1974)
Directed by award-winning filmmaker Robert Altman, he captures the non-stop gambling action and the wild lives of two southern California high rollers, played by George Segal and Elliot Gould. Most of the scenes take place at the race track or in a casino. The two friends end up in Reno playing in a high stakes poker game in order to solve their financial problems.
Lucky Girl (2001)
Normally, I would not recommend a TV movie, but this one happens to star Elisha Cuthbert as a high school girl who's addicted to gambling. She plays poker, runs a football book at school, and gambles on the internet using her mother's credit card. When she gets in over her head, a local loan shark agrees to help pay her debts if she has a sexual tryst with him and his wife.
High Roller: The Stu Ungar Story (2003)
Michael Imperoli plays Stu Ungar, the three time World Series of Poker Champion, in a movie about his tumultuous life as a genius card player who ruined his brilliant career when he became a degenerate gambler and drug addict. There are actually more gin rummy scenes than poker scenes, since a lot of the movie takes place during Stu's childhood and teen years when he was a gin rummy prodigy. The later scenes show the dark side of Stu Ungar as he spirals out of control and loses all the money he won playing poker.
Big Blind (1999)
This is one of the few films actually written and directed by someone who plays poker, a fellow named David James. It features cameos by professional players Scotty Nguyen and Jen Harman and focuses on the life of southern California card players. The poker scenes are realistic but the plot is very thin.
Warren Beatty stars in a film loosely based on the Ian Fleming book Casino Royale, which was made into a James Bond film. There are no spies in Kaleidoscope, but Beatty plays a young hustler who's working the casinos in Europe.
Ocean's Eleven (2001)
There is only one poker scene in Ocean's Eleven, but it's the funniest scene in the entire movie. Brad Pitt teaches young Hollywood stars how to play poker in the back room of a trendy night club and they end up losing their money to Danny Ocean, who was just released from jail. The rest of the film involves a plot to rob three casinos. The majority of Ocean's Eleven was shot on location in Las Vegas and is one of the most underrated films ever directed by Steven Soderbergh.