Gambling on an Oscar: Seven Gambling Movies that either could have, should have or did win an Oscar

Movies about gambling will most likely never go out of fashion because they are inherently about risk; and where there is risk there is usually excitement, a huge amount of ecstasy and often utter misery. You love watching them and we love writing about them; here are seven films; all of which contain gambling at the heart of them.

Rounders (1998)

Often quoted by professional poker players as the greatest ever poker movie, Rounders is a cult classic and is a movie synonymous with the lifestyle of the super smart but incredibly degenerate gambler. Matt Damon plays the title role alongside Edward Norton as their two characters; Mike and ‘Worm’ travel around the USA to play high stakes poker games in order to pay off a large debt instigated by Worm. The debt occurs due to the dishonest Worm who mounts up a number of debts to various characters, some debts he even makes out in Mike’s name. Rounders is a roller-coaster ride of a movie with plenty of ups and downs. Although Rounders received mixed reviews after it was released, it gained cult status during the poker boom of the early/mid 2000s.

If you have even a modest interest in poker then we would recommend you watch Rounders – it certainly is not a feel-good film, but it is full of action, suspense and emotions. No Oscar awards here, but its cult status ensures that Rounders is better remembered than 90% of all Oscar winning movies.

Lucky You (2007)

Eric Bana stars in this film as a young and upcoming hot-shot poker player attempting to escape from the shadow of his even bigger hot-shot poker-player and estranged father L.C. Cheever (Robert Duvall). Lucky You looked to take advantage of the huge serge in the popularity of both offline and online poker in 2007. Unfortunately, the story here has been told thousands of times before – superstar son has a complicated relationship with his more successful father which finalises into an eventual showdown before their relationship is restored – only, Lucky You tells the story from the point of view of two poker players. In fairness, the characters of the father and son are portrayed nicely by Bana and Duvall. However, it is safe to say that the Oscars were correct to avoid this movie.

Ocean’s Eleven (2001)

If the gamblers in Rounders are a realistic portrayal of poker players and gamblers in America, then the gamblers in Ocean’s Eleven, Danny Ocean and Rusty Ryan, portrayed by George Clooney and Brad Pitt respectively, are characters who real life gamblers wish they could be. With that being said, Ocean’s Eleven exudes the cocky spirit of modern Las Vegas whereby the film maker nor the characters are particularly interested in gambling, moreover their premise is to look good and sport the swagger that real life gamblers wish they had. A great promotional film for the now numerous online casinos which have become popular thanks to the internet, Ocean’s Eleven portrays gambling through rose tinted spectacles as something fun, dangerous and intensely cool. Ocean’s Eleven is regarded by many as one of the most exciting films of the noughties.

Ocean’s Eleven was a huge box office success which spanned two sequels: Ocean’s Twelve and Ocean’s Thirteen. A spin-off with an all-female cast, Ocean’s Eight was released in 2018. Did not win any Oscars but who cares, the film does everything it set out to do, and more.

Molly’s Game (2017)

Molly’s Game revolves around the character of Molly Bloom, a former champion skier turned underground poker queen. Molly becomes queen-bee of organising high stakes underground poker games. The thrills which Molly’s Game showcases is how highly addictive and lucrative the illegal gambling scene can be. Molly is played by Jessica Chastain who does a fantastic job of showcasing the characters cocky and confident self. Molly’s gambling rush is felt by all as you follow her through this underground realm. Molly’s Game contains some truly heart-breaking characters, however, who are as desperate as they are pathetic. The two extremes of a life in the world of high stakes gambling is very evident throughout this film. No Oscars here.

The Sting (1973)

The Sting is an absolute classic of cinema and is a gambling film filled with pure pleasure. Two conmen, Shaw and Kelly (played by Paul Newman and Robert Redford) take down a mobster in a film that will have you cheering and rooting for the good guys throughout. Shaw and Kelly set up a master con plan in which they attempt to take down the mobster. The Sting brought grifting to mainstream cinema and it is through brains rather than brawn that the good guys are able to come out victorious. This film is a must watch and even won The Best Picture award.

A Big Hand for the Little Lady (1966)

Also known as Big Deal at Dodge City for UK audiences (but we will call it by the USA title), A Big Hand for the Little Lady is a western film starring Henry Fonda, Joanne Woodward and Paul Ford. The films huge twist at the end (which I will not spoil here) ensures that this film goes down as this writer’s personal favourite on the list. The film begins with five of the richest folks in town getting together around a poker table. During the big game, a wagon passes through with the characters of Fonda and Woodward on the back of it. After the wheels come loose, one of the poker players becomes infatuated with Woodwards character – a former gambling addict who is drawn back into playing poker. Unfortunately, no Oscars here despite a twist that would rival the film SE7EN.

California Split (1974)

California Split is filled with lots of gambling, boyish friendships and a sucker punch of an ending. This film was ranked as the best gambling movie of all time by Vulture so if you have not seen this one yet, it is a must watch. Similar to Molly’s Game, California Split showcases the weird and downright dangerous characters that populate the world of underground gambling. But through gamblers Charlie and Bill, the movie also explores a movie from the point of view of a great friendship in a world full of cheaters and frauds. Charlie has a pretty severe addiction, but we won’t spoil anything for you.

Despite its high reviews, California Split was not nominated for any Oscars, however, it was nominated for a Best Comedy Writers Guild of America award.

About RJ Frometa

Head Honcho, Editor in Chief and writer here on VENTS. I don't like walking on the beach, but I love playing the guitar and geeking out about music. I am also a movie maniac and 6 hours sleeper.

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