5 Best Gambling Movies Of All Time

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The Cooler

Coolers” are people whose luck is so bad that they can change a player’s hot streak with nothing more than their presence. William H. Macy seems to have been born for this role. The premise of this movie, however, takes the concept of the cooler to another level. Macy’s performance is as close to perfect as any on this list, and the premise is a fun one as well. If you want to learn about how gambling pros handle the concept of luck, this is a great movie to watch as well.


This movie features one of the seminal performances of a young Matt Damon, who plays his way through college using poker. Damon is definitely a force to be reckoned with, but the supporting cast is nothing to sneeze at, either. You have Edward Norton and John Malkovich sitting as Damon’s rivals, with Norton giving an especially insightful performance. If you have never really taken a look at the psychology that goes on at the poker table, this is a great introduction to the sport inside the sport.


This movie is based on a true story, and it is one of the best examples of “truth is stranger than fiction” of any gambling movie ever. The cast is stellar, featuring a number of Hollywood stars. However, one of the reasons that this movie is so good is because it speaks to the future of a connected online world of gambling that did not yet exist during filming. Casinos like Casumo were little more than a twinkle in some webmaster’s eye. The hedonism and the personal betrayal adds a nice layer of drama to the plot as well.

The Sting

Robert Redford and Paul Newman make a great team in this tale of talented con men who target a jet setting crime boss with a weakness. This boss made his bones off of gambling, and he can’t turn down a good gamble. The game of the long con is essential to understanding this movie, because nothing is as it seems from the first scene. This is a long crescendo that will draw you in and keep you hooked for the entire thriller. You will see a lot of the twists and turns in this movie show up in many of the gambling movies that came after.


What is a list of top gambling movies without perhaps the most famous and highest grossing gambling movie of all time? Casino is an epic story of the mob, early stage gambling and development in Las Vegas, and a web of personal narratives that you will have to watch multiple times just to understand the basics of. Robert DeNiro works with his long time movie brother Joe Pesci to weave one of the best buddy tales of this century. Sharon Stone gives perhaps one of the best performances in her long career, putting the cherry on the sundae of this incredible film.


Agree or disagree? I bet you can’t go through this list one time without wanting to watch at least one of these movies (again). If you want to rekindle your love for gaming before heading out to Vegas (or staying in and playing online), pop in the old VHS, CD or hit Netflix and find one of these amazing films to whet your appetite!