Tombstone

A kick-ass western that doesn't sweat its lapses in historical accuracy, and delivers some major entertainment value start to finish. Competent performances by Kurt Russell, Sam Elliot, and Bill Paxton as the Earps are overshadowed by Val Kilmer's turn as "Doc" Holiday, gambling, boozing, quick drawing icon of the old west.
Doc: "I'm your huckleberry."

California Split

Old school poker. "California Split is a 1974 film directed by Robert Altman and starring Elliott Gould and George Segal as a pair of gamblers.
The film is less concerned with plot than behavior as we watch the friendship between Bill (Segal) and Charlie (Gould) develop over a mutual love of gambling. Charlie is a wisecracking joker and experienced gambler constantly looking for the next score. Initially, Bill isn’t as committed a gambler (he works at a magazine during the day) but he’s on his way. As the film progresses and the two men hang out more, Bill starts to become more addicted to the gambling lifestyle." source: Wikipedia.
Keep an eye out for a very young Jeff Goldblum, and Amarillo Slim playing himself.

Rounders

The movie that started it all. Stellar performances by Ed Norton, Matt Damon, Martin Landau, and John Malkovich as Teddy KGB make this more than just the movie that has drawn millions into the "poker boom" of the 21st century. Despite flaws that keep it from being totally believable Rounders is an engaging, satisfying movie start to finish. One major flaw (without which there would be no movie) is that the protagonist, Mike, is supposed to be a master of reading people, but is blind to the fact that his best friend and his girl friend are respectively a sociopathic loser and a tight-assed, whining scold. And it takes the whole movie for him to wise up and dump the both of them.

The Cincinnati Kid

Steve McQueen as the ultimate cool poker pro. The poker scenes carry half the movie, and Steve's cool carries the rest. The final hand of five-card stud in which the Kid's aces-full is beat by Lancey Howards's straight flush is laughable, but somehow manages to work well enough to pull off the dramatic finish.

The Final Hand

Honeymoon in Vegas

Another movie in which the plot turns on the outcome of a poker hand, causing Nic Cage to lose his fiance for a week end. The hand in which James Caan as the wealthy poker pro beats Cage's straight flush with a higher straight flush would cause most players to suspect he'd been cheated. Fortunately for the film, Cage's character misses that possibility altogether, and pursues Caan and his girl friend to Hawaii and back to Vegas.

Maverick

A turn-off-your-brain, popcorn munching, intermittently enjoyable, light-headed flick that beats out Cincinnati Kid for the most unbelievable, contrived final hand of poker in any movie. Makes Mel's competent acting turns in Road Warrior and Braveheart look like aberrations. Even the charm and acting chops of James Garner and James Coburn can't save this train wreck of a movie.

Lucky You

Notable mainly for numerous cameos of well known poker pros from Doyle Brunson to Jennifer Harman to Sammy Farha, Lucky You means well, but the by-the-numbers story of the self-destructive poker pro with daddy issues who finds love on his way to the World Series of Poker, never quite catches fire. The feeble WSOP scene near the end is weak, and conveys none of the flavor of either the ESPN broadcasts or the actual event. Check out the touching scene where the hero (played by post-Hulk Eric Bana) knocks Jennifer Harman out of a tournament. The look in her eyes almost broke my heart.

House of Games

Stilted, unrealistic dialogue (okay, it's David Mamet), a bizarre, high school drama club level performance from the leading lady (okay, it's Mrs. David Mamet) can make House of Games tough to watch. Yet, the twists and nicely laid out steps of the plot make this worth viewing. Check out the deadly serious poker hand that ends with the discovery of a squirt gun.