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Some of the Best Gambling Movies of All Time

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There are countless iconic films out there about gambling: way too many to count, in reality. Sometimes it’s not easy finding a movie to watch so I looked through the movie archives and picked out what we consider are some of the best gambling films of all time. There were several awesome movies that unfortunately didn’t make the list and of course, you might agree with some of the choices or disagree completely, as this article is based on MY personal opinion.

High Roller: The Stu Ungar Story

The affectionately named Stuey portrays Michael Imperioli as Stu Ungar, a high roller notable for being the first poker player ever to win three WSOP Major Event tournaments, one of the greatest biographical gaming movies ever. The spectacle of A.W Vidmer is no high-octane thriller but shows the breakdown of a man who once had it all. The story portrays the whole life of the gambler, from start to finish, showing big positive moments but also big negatives.

The Cooler

In Wayne Kramer ‘s film William H. Macy plays an unusual character. Macy is the title’s ‘cooler’-a guy whose luck is so poor that casinos need him to stay on hot streaks at the punters table. Their luck improves without delay, and the bottom of the casino ‘s house is repaired. But when the cooler’s own fortunes change, he suddenly finds himself the lucky charm of every Vegas gambler- much to the chagrin of the casinos that employ him. An enjoyable idea backed by a fantastic core show, this is a perfect look into the superstitions of casino gaming and the definition of luck.


Rounders features a young Matt Damon and is the tale of a businessman who pays for his university tuition fees by winning at the poker table. The film is full of familiar celebrities, with appearances by John Malkovich and Edward Norton. The battle of the film culminates in a sparkling game of high stakes, with Malkovich portraying the irrepressible poker baron Damon must seek to beat. Brilliant performances take the film along – Norton, in particular, is excellent – and realistic representations of poker tactics and table chatter that few other gambling movies can effectively make.

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The Cincinnati Kid

Another movie with a number of decent actors, The Cincinnati Kid, featuring Steve McQueen, tells the story of an up-and – coming gambler who is pitting his wits against the day’s high roller, Lancey Howard. Played with verve by Edward G. Howard, Lancey agrees to take on McQueen, seeing that the Kid had only made his name in games with little serious competition in the backroom. The Kid is further hampered by a series of distractions – including a beautiful girl – that threaten to overthrow his chances. The film culminates with both players raising their stakes, with one of them thrillingly coming out on top in an explosive finale.

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