Feature: Raking in the Big Bucks: Five Movies that Are all About Winning Money

It Could Happen to You

Watching movies about winning big is almost as exciting as the real thing. Whether the film is about winning money online or about con-artists in the old west, the following five films are some of the most entertaining movies about gambling ever produced.

Ocean’s Eleven

This 2001 film is a remake of the popular ‘Rat Pack’ thriller. Starring Julia Roberts, Brad Pitt, Matt Damon and George Clooney. The movie takes place in Sin City and revolves around Danny Ocean’s desire to take on three Las Vegas casinos. Steven Soderbergh directed the first in a series that includes Ocean Twelve (2004) and Ocean’s Thirteen (2007).  Not only is the movie about gambling, it includes raking in the big bucks through high-tech thievery and intrigue.

Runner Runner

Runner Runner was released in the United States in October 2013. As an American crime thriller, it provides a fascinating look at online casino. Central actors include Ben Affleck, Justin Timberlake, Gemma Arterton, and Anthony Mackie. Directed by Brad Furman and produced by Jennifer Davisson Killoran, Leonardo DiCaprio, and Arnon Milchan, it was released outside of the USA in September 2013. Based in part on the exploits of the professional gambler, Nat Arem, the movie met with less than favourable reviews. The main character in Runner Runner, Richie Furst, uses online gambling as a way to payoff for his master’s degree at Princeton; from there the events unfold.

It Could Happen to You

Winning, money and romance… It Could Happen To You offers a lighter perspective on gambling. Charlie Lang (Nicholas Cage), not only wins big, he chooses to use his earnings for the good. True to his word the New York City cop, Charlie, offers half of his lottery winnings to his waitress, Yvonne, played by Bridget Fonda. With his marriage in a downward spiral, good-hearted Charlie wants to make things right in this romantic comedy about playing the odds.


Based on actual events, 21 was released in 2008. The story revolves around a Blackjack Team of MIT students who successfully learn to count cards. The team takes their newly acquired skills to Las Vegas, Nevada. In LV, they are able to use mathematic reasoning to challenge the system and win big! The film was directed by Robert Luketic and stars Kate Bosworth, Kevin Spacey, Aaron Yoo, and Jim Sturgess. Based on the successful book by Ben Mezrich, ‘21’ was a blockbuster. The dramatization includes suspense, romance, action, ingenuity, as well as raking in the dough. When main character Ben Campbell decides to use gambling as a way to finance his education at MIT, a series of events affect his plans.


Based on James Garner’s character in the 1950s-television series, Maverick is a 1994 action-comedy about a gambler who sets out to win. The movie stars James Garner, Mel Gibson, and Jodie Foster. In this western with a twist, Bret Maverick (Gibson) requires an extra three grand to take part in a ‘winner-takes-all’ game of poker. Maverick seeks to collect on outstanding debts and becomes involved in the activities of Annabelle Bransford (Jodie Foster), and Marshal Zane Cooper (James Garner).

Each of the above movies is unique in its own way. As the characters rake in the bucks; these films successfully win over the viewers!

Author: Guest Post

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