Gambling has always been a popular ‘meme’ with film directors ever since Georges Méliès first pioneered moving pictures back in the late 1890s. For decades, no cowboy film was considered complete unless it featured a scene in which some black-hatted buffoon suffered a bullet-induced puncture after being discovered cheating at poker.
Cowboy movies may now have gone the way of double features and choc ices, but the odd gambling-themed movie – or at least a film with a notable gambling-related scene – still pops up every now and again, with just about the same frequency as does a reason to laugh at an Adam Sandler ‘comedy’.
Here we run down five of the best gambling-themed movies ever committed to celluloid:
Nothing to do with the juvenile version of baseball, Rounders is a classic cult movie that slipped under the radar when it was released in 1998. It is centred around two high-stakes Texas Hold’em players, who in the film are portrayed by Matt Damon and Edward Norton. Damon stupidly loses his entire $30,000 poker bankroll on one hand, and subsequently has to claw his way back up from the edge of bankruptcy.
Vowing to leave the cards behind, Damon tries to revert to a normal life, but a chance meeting with his buddy, played by Norton, draws him in once again under the spell of flops and showdowns.
Even if Texas Hold’em leaves you cold, this film is worth seeing for John Malkovich’s hit-and-miss portrayal of a poker-loving Russian mobster.
 The Hangover
Three friends (and a slightly weird hanger-on played with great applomb by Zach Galifiankis) head to Vegas for a stag party. Drunkenness ensues, and one party member vanishes. Convinced he has been kidnapped, the remaining trio must find $80,000 in order to pay the ransom. Galifiankis goes all Rain Man and wins $82,400 by card-counting at blackjack. It turns out that the guy who’d been kidnapped was not their friend at all, but a local lowlife.
The movie features several notable scenes, including the theft of Mike Tyson’s pet tiger, and that age-old motoring problem – the unexpected discovery of a naked Asian man in the boot of one’s vehicle. A massive hit in 2009, this movie went on to spawn two equally massively-disappointing sequels.
Another film with a blackjack theme, 21 is based on a true story. An MIT professor gathers together a team of number-crunching geniuses in order to teach them about card counting, and how it reverses the house’s edge so that the player has the advantage. The team hit Vegas and are soon swimming in chips, but they run into issues with a casino’s security team who are not too over-the-moon at the way the students are ‘legally swindling’ the live dealers at the tables.
In real life the ‘MIT Blackjack Team’ managed to keep their card-counting ‘trickery’ up and running for well over a decade, earning on average $170 an hour at casino blackjack tables. The success of the MIT team ‘inspired’ casinos to introduce more frequent shuffling. Contrary to gambling myth, you can’t count cards whilst playing blackjack online, even when playing at live dealer casinos. For more information on how these work, check out this comprehensive guide on live casinos.
Named after a dice roll in craps, this movie is probably another one that has passed you by. An ageing pro gambler played by Philip Baker Hall bumps into and takes pity on a guy (John Reilly) who is in Vegas trying to win enough money to pay for his mother’s funeral. Hall takes the young man under his wing and teaches him how to gamble properly, and with some success. It later transpires that all is not as innocent and above board as it seems. This was one of the first movies directed by Paul Thomas Anderson, who went on to direct the Oscar-winning There Will Be Blood, starring Daniel Day Lewis.
 Ocean’s Eleven
The original fun-filled casino-heist movie, Ocean’s Eleven was originally released as a brat-pack movie in 1960, but most people will know it better from the 2001 remake which starred George Clooney, Matt Damon and Brad Pitt. Clooney plays conman Danny Ocean who, on his release from prison, decides to commit a daring heist on a trio of Las Vegas casinos all at the same time. He recruits a team of thieves and other talented hoodlums to help him pull off the heist, all in the hope of robbing the casinos of $150 million. Like The Hangover, this movie too was followed by two less-than-stellar-sequels.