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February 13, 2019

5 Historical Gambling Movies


You can trust Hollywood to turn a casino game into an exciting affair. It’s not that playing blackjack or poker isn’t exciting in real life; it’s just that there is an added flair when a gambling scene is translated for the screen.

In a movie, audiences can sense the tension in the room thanks to some acting, carefully selected shots, and well-designed sets. In some cases, gambling scenes even contain interesting dialogue (case in point: that mahjong scene in Crazy Rich Asians). And in others, gambling or the attempt to can be a source for laughs. Here’s a brief journey through movies that feature gambling:

Swingers (1996)

Before Jon Favreau directed big-budget movies, he wrote his own (and directed some of them). Swingers is one that he wrote based on his own experience, and it was a hit with movie-goers. One of the most interesting scenes in the film involves gambling (of course).

Swingers (1996) film scene
Swingers (1996) - The scene at the blackjack table

In the movie, Favreau’s character Mike is heartbroken. His friend Trent (played by Vince Vaughn) suggests a trip to Last Vegas will help him recover. So what does one do in the city? Hit the casinos, obviously.

The blackjack scene in this movie is memorable for the phrase “always double down.” It’s also a great example of listening to your gut vs the devil on your side (in this case, a friend). Trent suggests that Mike double his $100 bet after being dealt an 11. Mike was clearly reluctant, even arguing with his friend before finally caving in. The dealer won in the end and the two friends move to a table with lower stakes.

The lesson there was: you don’t always double down on 11.

Rounders (1998)

Before Matt Damon starred in Ocean’s 11, he played the protagonist in this film. Like the young Hollywood stars in the first Clooney-led Ocean’s movie, Damon too had to go through a similar “tutorial” about poker playing in preparation for his role.

Unlike the other movies in this list, Rounders features quite a few poker games. Of all, the most interesting was the final showdown between Damon’s character, Michael McDermott, and the character played by John Malkovich, Teddy “KGB”. It was definitely a thrilling scene with a lot on the line for McDermott.

The film also highlights the allure of high-stakes poker and its associated dangers.

21 (2008)

Based on the best-selling book Bringing Down the House by Ben Mezrich, 21 follows a group of MIT students who are taught by their math professor to count cards, which is illegal. Although the film was controversial for its choice of cast, it was nonetheless a success at the box office. While entertaining, the movie also serves as a cautionary tale: the combination of cheating and gambling can cause a lot of problems.

The events Mezrich writes about in his book are based on real-life events that involved the MIT Blackjack Team, a group that used card counting in order to beat casinos at blackjack. Card counting can be best described as memorizing the cards that have been handed out.

Doing so helps you decide whether to bet big or small thereby increasing your chances of winning. While this sounds appealing, it’s tough to carry this out on the best online casinos since cards are almost always shuffled after each round. Your best bet in testing this out is at an actual casino (it’s not illegal but it is frowned upon) or you can play a few rounds of your own at home. At the same time, practicing can give you the confidence needed when you finally play blackjack online. Just remember to bet wisely and know when to quit.

Ocean’s 11 (2001)

This movie is about robbing three casinos - all owned by one individual - and it isn’t surprising to have it mostly set in such an environment. One of the movie’s best scenes comes at the early stages: when George Clooney’s character Danny Ocean gets out of prison then heads to recruit his longtime collaborator Rusty (played by Brad Pitt).

Pitt’s character is teaching young Hollywood actors how to play poker but they can’t seem to grasp the idea. Clooney’s character comes in to join them and he and Rusty end up conning the young celebrities.

Casino Royale (2006)

A list of gambling in films will never be complete without mentioning this gem. The gambling scene also delivers in terms of drama and excitement. Can you imagine your opponent coming back from an initial mess up as well as an intentional poisoning? This is what happen in one of the most legendary poker match, where the main character (Daniel Craig) as James Bond, have to win a stratospheric sum to counter terrorists financing.

The films listed here showcase a dangerous side to gambling. You will lose money along the way but being careful and cautious prevents you from losing your entire fortune.


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