There are few popular true poker movies followed by some movies where poker doesn't have a big chunk of the screen time but nevertheless contain especially memorable poker scenes.
High Roller : The Stu Ungar Story (2003)
Michael Imperioli (The Sopranos) portrays one of the legendary poker players of all time, Stu Ungar, who won 3 WSOP tournaments (the only player ever to do so) and countless other tournaments. He won many millions at the poker table but lost everything due to horse races and his drug addiction that also led to his death in 1998.
Imperioli shows Ungar’s complex personality, wild lifestyle and incredible prowess at every game he played, whether it was blackjack, poker or gin rummy (his specialty).
The movie focuses on Ungar’s relationships with his wife and those closest to him and portrays his life from its beginning, on Manhattan’s lower east side, as a gin rummy prodigy, turning poker pro in Las Vegas, after escaping there due to debts brought on by his race horses addiction and finally, his poker playing days, legendary WSOP wins, drug addiction and his untimely death in a Las Vegas hotel room.
The Cooler (2003)
This film is unique among gambling films because it tells the tale of a man who is not a gambler, but rather a man who brings bad luck to other gamblers.
William H. Macy is Bernie Lootz, a man with such incredible bad luck that he makes it impossible to win when he’s around. He is employed by a Las Vegas casino to “cool down” winning gamblers at the tables.
When he falls in love with Natalie (Maria Bello), a waitress at the casino he works in, it suddenly turns his luck upside down. When people start winning big simply because he stands next to them, the casino owner, Shelly Kaplow, played by Alec Baldwin (who was nominated for both the Oscar and the Golden Globe for his performance) begins to intervene and to make Lootz’s life a living hell.
Luckytown (2000)
If you find your dad, what happens next? When she turns 18, unhappy Lidda Daniels leaves Southern California to look for Charlie, her father, a professional gambler who abandoned her years before.
On her way to Vegas, she picks up Colonel, a video store clerk whom she finds attractive even though they've never spoken. He is happy to go, in part because he sees himself as a great poker player.
Rounders (1998) 
Matt Damon is Mike McDermott, a New York law student who plays poker to finance his education. When he loses his savings in a $30,000 hand of poker he decides to quit the game completely until his old partner Worm, brilliantly played by Edward Norton, gets out of prison and drags him back to the game and into serious trouble.
The film is an atmospheric character study of the world of gambling that leads to the unavoidable final game that determines the fate of both friends when they face the dreaded Teddy KGB (John Malkovich) in a thrilling poker dual. The film brought many people to the poker tables and is one of the reasons poker became such a popular game in the last ten years.
Croupier (1998)
Clive Owen stars as Jack Manfred, an uninspired writer who works as a croupier in a casino only to find out that his life would make a great novel. Tensions begin to emerge between Jack and his girlfriend, Marion, played by Gina McKee, when he finds himself succumbing to the temptations of the gambling world. Jack begins to realize that he is becoming the hero of his novel, the immoral Jake, and is, in fact, giving in to these temptations to provide him with subject matter that will make for a memorable work of fiction.
This neo film noir movie portrays a thrilling profile of the life of a dealer and shows how real casinos operate, while telling a compelling story.
Lock, Stock and Two Smoking Barrels (1998)
This movie isn't about poker, but it's the high-stakes undergroung game of three card brag that puts the whole movie in motion. After three friends stake the fourth, Eddy, to play in the game with Hatchet Harry, Eddy ends up not only losing all the money they gave him, but an additional half-million pounds. How they try to get the money to pay Hatchet Harry back is a hysterical, action-packed ride, which is well-worth watching.
Casino (1995)
Based on the book by Larry Shandling and Nicholas Pileggi, Casino was released in 1995 and was directed by Martin Scoresese. It stars Rober De Niro (who else?) as Sam "Ace" Rothstein, a character based on Frank Rosenthal, who ran casinos in Las Vegas for the Mafia in the 70’s, most notably the Stardust casino.
The Mafia is backing Rothstein while he secretly runs the casino and has to set up a false front while, because of his gambling charges back East. Nicky Santoro, played by Joe Pesci, is sent by the mob to look over Rothstein and protect him but he eventually runs his own operations. Sharon Stone plays Ginger McKenna, a former prostitute and Rothstein’s love interest, who remains in love with her pimp, Lester Diamond, portrayed by James Woods.
Maverick (1994)
This movie won't teach anyone how to play poker, but it is a fun film that captures the old-west image of back-alley bars, cowboys, and cards. Maverick, played by Mel Gibson, travels with the original Maverick, James Garner, and Jodie Foster to the biggest poker tournament of the day -- a riverboat five-card draw winner takes all contest.
Honeymoon in Vegas (1992)
Once again, a plot is put into motion through people cheating at poker when Nicolas Cage loses his girlfriend for the weekend when his straight flush is beat by James Caan's higher straight flush. Now, I would have perhaps suspected cheating here, but thankfully Cage's character isn't that bright, because then we'd miss out on his crazy antics from Hawaii back to Vegas to get the girl back.
The Gambler (1974)
James Caan is Axel Freed, a professor in a New York City university that ironically also teaches Dostoyevsky’s The Gambler in his course. Despite his familiarity with gambling addiction and his use of Dostoyevsky to intellectualize his weakness into tragic compulsion he has a gambling addiction bordering on a tendency of self destruction.
The film presents a gritty realism to the world of bookies, loan sharks, and their violent enforcers. This intensive and realistic presentation of the life of a gambler on the path to self destruction is both compelling and disturbing. Not many films before or since have managed to capture the thrill of gambling, the constant risk taking and living on the edge, as this film managed to do so well.
The Sting (1973) 
The Sting is an excellent con movie which is considered to be among the best 100 pictures ever made. Starring Robert Redford as "Johnny Hooker" a young con man who seeks the help of oldtimer Henry Gondorff played by Paul Newman to get revenge on a crime boss "Doyle Lonnegan" who had his partner killed.
This isn't really a poker movie but it does contain one famous poker scene where Paul Newman cheats the crime boss in a high-stakes game onboard a train and also has a scene where Paul Newman's character shows off some very skilled cheat shuffling, although the hands seen belong to John Scarne who was one of the top gambling experts in the last century and served as technical advisor on The Sting.
The Cincinnati Kid (1965)
It's New Orleans and a new kid has come to town to beat the notorious Lancey Howard (Edward Robinson), the best poker player in the country. With the help of an old friend and card dealer, Eric Stoner (Steve McQueen) manages to get in on the highest stakes game of his life. The Cincinnati Kid is all about the poker scene at the end, which is one of the best on film for certain. However, you must sit through some reasonably flat performances revolving around revenge and romance to get there. There are a couple of good moments of sexual tension between McQueen and Ann-Margret (playing Melba) in between Steve truly wanting to be with Christian (Tuesday Weld). Caveat; this is one of the best poker movies, not necessarily movies alone.
A Big Hand for the Little Lady (1966)
Henry Fonda (Meredith) and Joanne Woodward (Mary) are a husband and wife, who get caught up in a high-stakes poker game on their way to California. Meredith gambles all their life savings on the game, money that was meant to be used to by a farm.
When Meredith suffers a heart attack during a hand his wife takes over, even though she doesn't know how to play. Will she be able to play against the professionals and save their life savings? The end will surprise you.
Kaleidoscope (1966) 
The movie tells the story of Barney Lincoln (Warren Beatty), a card player that comes up with a great way to cheat at card games. The young playboy’s scheme is to break into a plant that manufactures all the playing cards to all the major casinos and mark the plates that are used to print the cards. The casinos, as he finds out, use the same playing cards, all manufactured by the same company. He then naturally begins to win everywhere he plays.
When his girlfriend, Angel McGinnis (Suzannah York) learns his secret and her father, an inspector at Scotland Yard finds out too, things start to get dangerous. Her father demands him to help him catch the criminal Harry Dominion in exchange to keeping his secret but things get worse when Dominion finds this out and he kidnaps McGinnis. Lincoln and Dominion then dual it out at the poker table for the game of their lives.
Some critics claim that the plot of the film is based on Ian Fleming’s Casino Royale novel, the first in the James Bond series, which has now also become the newest James Bond film, after Die Another Day, which came out in 2002.
Sunset Trail (1939)
A good guys versus bad guys movie with Hopalong Cassidy as the hero. Keller, the bad guy buys up a farmer's cattle then kills him and steals the money. Hopalong finds out that this is the case by posing as a newbie poker player and getting the farmers daughter to check the serial numbers on the cash (yeah, I know). I won't go into too many details, but poker is used to triumph over evil in the end and that is why this movie is so fantastic.
