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(2007) Lucky You
How can you beat a casino-themed movie titled, Lucky You? You can't, at least it would be very hard to. Not only that but this movie actually gives its audience a look inside professional poker. That's right, in this movie, the audience will get to see the main character traverse the murky world of the World Series of Poker. It doesn't stop there. Along the way, you will see him battle not only with the tournament woes but he will vie for the heart of a talented Las Vegas signer.
(1989) Let It Ride
This one is a bit of an oldie but it is hard to beat the classic and that's exactly why Let It Ride is number 2 on the list. You won't find the main character using the best baccarat strategy because he is a horse gambler but you will get a kick out of the wacky comedic 80's format. Richard Dreyfuss plays the main character in this one and he is a bit of a gambling loser until he hits it big one day on a horse race. What does he do from there? He only bets bigger and wilder until he finds himself in worse shape than before he hit his big jackpot.
(1995) Casino
You simply cannot have a list of casino movies and not mention the granddaddy of them all, Casino. If this movie teaches gamblers anything, it will be that you really have to watch everybody else more than you do yourself. This one features some of the greatest Hollywood talents like Robert De Niro, James Woods, Sharon Stone, and Joe Pesci. On top of that, it is directed by Martin Scorsese. De Niro plays a gambling expert and is asked by the mob to oversee a casino and hotel operation in Las Vegas. You can imagine the difficulties of running a hotel/casino resort but get the mob involved and things only get that much more difficult, as you will see.
(1961) The Hustler
Many gamblers will likely tell you that The Hustler's sequel, The Color of Money, is a much better gambling movie, but that's hardly the case at all. Most people probably say this because The Color of Money features a very young and swaggering Tom Cruise. The original stars Paul Newman and his character is much more interesting that Cruises. Loyalty, ambition, and integrity are his things. You will also find that the original story arc takes on more of a human, soulful narrative as compared to the sequel's sporty movie arc. It's also worth mentioning that this one was also directed by Martin Scorsese.
(1973) The Sting
Here's another oldie but goodie. The really neat thing about The Sting is that it shows people just how much fun gambling can be. That is unless you run into the two main characters, Shaw (Paul Newman) and Kelly (Robert Redford). There are two con men who decide to ply their trades on a no-good mobster, Robert Shaw. Their big grift is an elaborate Ocean Eleven's-like scheme that involves everything from card games to horse racing. One good thing about the movie is it doesn't matter if you don't understand the complexities behind the grift because the characters are a blast and the content is a true pleasure to watch.
(1998) Rounders
Loyalty and integrity were mentioned earlier. Well, it is hard to beat the loyalty and integrity that comes along with Matt Damon's character in this thriller. Damon plays the friend of Edward Norton, who was just released from prison and gets himself into a bit of debt with a shady fellow. Damon has just promised his girlfriend that he is going to give up gambling but gets back into it to save his friend. You simply can't get more loyal than that. This one is a blast to watch from beginning to end and will get you on your toes the whole way.