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From Ocean’s Eleven to Casino – Our Favourite Gambling Capers

While it may have been recently revealed that the late Sean Connery’s stunning roulette win in Italy was staged as part of a European marketing campaign for ‘Dr No’, there remains a sense of romance and innate excitement attached to casino gambling.

This has been captured by numerous films throughout the years, many of which showcase different aspects of casino gambling and the psychology behind this popular practice.

But which of these films are the best to have hit the silver screen? Here’s our pick of the top four!

Casino (1995)

When Robert De Niro starred in the hit gangster film ‘Mean Streets’ in 1973, he portrayed the unpredictable and violent hothead alongside Harvey Keitel’s cool, composed and rational mobster.

Fast-forward 22 years to 1995 and Martin Scorsese’s hit film ‘Casino’, however, it was De Niro who played the role of responsible gambler in the form of casino owner Sam “Ace” Rothstein. 

In this dark and spitefully violent film, De Niro’s character strives to manage a mobbed-up casino lawfully while optimising legal profits. 

At the same time, De Niro’s hot-headed henchman and childhood friend Nicky Santoro (Joe Pesci) cannot help but thwart his pal’s plans and undercut him at every turn, while ambitious love interest Ginger McKenna (Sharon Stone) also complicates the lead character’s life and career.

A well-constructed thriller with a penchant for violence and excellent narrative, Casino excels and provides an excellent follow-up to the previous hit Scorsese movie ‘Goodfellas’.

The film also provides an excellent vehicle for Scorcese’s innate understanding of American enterprise within the criminal underworld and gambling industry, highlighting its ruthless nature and just how lives can be destroyed over time.

Rounders (1998)

In terms of gritty and hard-hitting gambling films, John Dahl’s ‘Rounders’ is arguably one of the very best to have ever gone into production.

Because of this, the film has earned a cult following among compulsive gamblers and become seminal viewing for addicts, while it’s a thrilling and thoroughly enjoyable watch for everybody else too.

Certainly, few films have proved as effective as capturing the swaggering masculinity of being a professional gambler or poker player, while the movie also explores the reality of such a career choice and a world that’s considered by many to be largely insincere.

There’s a stellar cast too, including Matt Damon, Edward Norton and the excellent John Malkovich. Such a hard-core line-up adds weight and credibility to the narrative, while transforming a potentially artificial realm into a corporeal and tangible space.

Of course, in an age where you can wager freely at a live casino online, the notion of face-to-face and in-person poker tournaments almost appears nostalgic.

However, this adds enduring appeal to what’s already a hit film, and one that remains one of the best gambling movies of all-time.

Ocean’s Eleven (2001)

On the subject of stellar casts, there are few films that pack the same punch as Steven Soderbergh’s blockbuster hit ‘Ocean’s Eleven’.

Released in 2001 to both Box Office success and critical acclaim, it’s also a remake of the 1960’s ‘Rat Pack’ film of the same name, while it spawned two sequels in what turned out to be a money-spinning franchise.

The movie stars George Clooney and Brad Pitt as the main stars, while the ensemble cast also includes names like Matt Damon (again), Don Cheadle, Andy Garcia and Julia Roberts.

As for the plot, the film tracks Danny Ocean (Clooney) and Rusty Ryan (Pitt) as they plot an ambitious $160 million casino heist, with ruthless entrepreneur Terry Benedict (Garcia) their target.

Ultimately, Ocean’s Eleven became the fifth-highest-grossing film of 2001, generating an impressive $450 million worldwide. 

So, it’s deserving of a place on our list, and while purists may not agree, we think that it does justice to the original Rat Pack film.

The Card Counter (2021)

Paul Schrader is well-renowned for creating taut and well-written dramas, with his 2021 hit ‘The Card Counter’ among the best that he has ever produced.

Sleek, brooding and anguished in equal measure, Card Counter relays the tale of a professional blackjack player who makes his money by travelling from one casino to another and playing competitively at tables.

However, Oscar Isaac’s lead character also travels from one location to another to assume some control over his troubled life, while also hiding from the guilt and torment that plagues him. To this end, the gambling scenes are incredibly gritty and far-removed from the glitz and glamour of the Vegas lights. 

While some may say that this makes such scenes uncomfortable to watch at times, they’re genuinely compelling and brilliantly acted by the perfectly-cast Isaac.

Although this film is quite different to most of the entries on our list, it’s well worth a watch and one of the more thoughtful movies to focus on gambling through history.

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