6 Best Gambling Movies You Have To Watch - Endless Popcorn

Best Gambling Movies

Who doesn’t like gambling a little!? Or maybe a lot!? We know we’re always up for a few games of Poker or Blackjack! Maybe even a little Roulette!

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We also love watching movies about gambling. Some of the movies on this list give you a firsthand look at just how incredible some gamblers are! While others reveal just how dangerous and addicting gambling can be.

We have put together some of the best gambling movies out there for you to watch! So, if you are in search of the best gambling movies, then you have come to the right place! Keep on reading to see what gambling films you absolutely need to watch!

1. Rounders

For the first film on this list, we start off with a Matt Damon classic! This movie is also reminiscent of Good Will Hunting because Damon is, again, quite a genius in this film! You absolutely have to watch this film if you haven’t seen it already!

Rounders Movie Description

After losing all his money, Mike McDermott (Matt Damon) promises his girlfriend Jo (Gretchen Mol) that he won’t partake in any more gambling. However, this all changes when a friend of his needs a favor. His friend, Lester Murphy (Edward Norton), is fresh out of prison and, for his own safety, must pay off some debt he owes to some dangerous people. Mike agrees to help him because the man Lester owes money to is the Russian gangster Teddy (John Malkovich), the same man who Mike lost all his money to. Mike sees this opportunity and decides he’ll give it one last go, giving it everything he’s got to defeat the Russian gangster.

Check out our post on the Best Matt Damon Movies You Can’t Miss.

2. 21

Here we have another boy genius who uses his amazing math skills to win a ton of money! Sometimes, watching these films makes one daydream about learning card counting and then walking into a casino to pocket hundreds of thousands of dollars! But then reality hits and the possibility seems remote, at best! We highly recommend giving this film a watch, it is incredible!

21 Movie Description

A genius kid named Ben Campbell (Jim Sturgess) made it into the prestigious MIT. However, Ben soon realizes that he doesn’t have the means to pay the tuition and needs to make some money fast. When one of his professors sees the potential in him, he asks Ben to join in a little club he has put together. Ben agrees and quickly finds out that the group the professor leads goes out to casinos and counts cards on the weekends. The group uses their impeccable math skills to win vast sums of money in Las Vegas. But as Ben will soon find out, he is playing a perilous game when he meets casino enforcer Cole Williams (Laurence Fishburne).

If you enjoyed this film you’ll also want to check out our post on the Best Gambling Movies On Netflix.

3. Mississippi Grind

Would you go on a road trip to gamble with a man you just met if you believed he was good luck!? Well, this guy did! And it may have paid off! The film also stars Ryan Reynolds, so you know it’ll be good!

Mississippi Grind Movie Description

Gerry (Ben Mendelsohn), a gambling addict, meets a fellow gambler named Curtis (Ryan Reynolds) and befriends him. In hopes of changing his horrible luck, Gerry goes on a road trip with Curtis in hopes of winning tons of money. The two men set off on a gambling extravaganza which also serves as a personal learning experience for both of them.

4. The Gambler

Mark Wahlberg, putting on another impressive performance! However, it seems the poor guy can’t catch a break with his gambling addiction! This film is stupidly intense and will have you on the edge of your seat the entire time! Go ahead and give it a watch, we definitely recommend it!

The Gambler Movie Description

Jim Bennett (Mark Wahlberg) leads two lives. During the day, he teaches literature at college. While at night, he leads a secret life of high-stakes gambling. However, Jim loses everything, in turn, spurring him to borrow money from a gangster in hopes of making back what he lost. When he also loses the borrowed money and is unable to pay it back, Jim knows his time is running out.

Here’s our list of the Best Mark Wahlberg Movies You Need To Watch.

5. Molly’s Game

This film is based on an insane true story! Once you watch this film, you won’t believe that this actually happened, but it did! We highly recommend giving this a watch as it is incredibly interesting and will keep you captivated the whole time!

Molly’s Game Movie Description

Molly Bloom (Jessica Chastain), known as an Olympic-class skier in the public’s eyes, has a secret. She has managed one of the worlds most exclusive high-stakes poker games for nearly a decade with no problem. The players in the games include high profile persons such as business titans, sports stars, celebrities, and more. However, everything goes awry when 17 FBI agents, all armed with automatic weapons, arrest Molly in the middle of the night. Now, the only person Molly can trust is her defense lawyer Charlie Jaffey (Idris Elba).

6. Win It All

For the final movie on this list of the best gambling movies, we have Win It All! This movie is comical and will keep your eyes glued to the screen the entire time! It also teaches a valuable lesson: never hold a duffle bag that someone has asked you to store for them! Give it a watch if you haven’t seen it!

Win It All Movie Description

Eddie Garrett (Jake Johnson), known for never winning while gambling, finds himself in a world of trouble. When an associate of his asks him to watch a duffle bag for him while he heads to prison, Eddie agrees. Curious to see what’s in the duffle bag, Eddie opens it to find an insane amount of cash. Against his better judgment, Eddie begins to slowly pick away at the cash, gambling it away and never winning. He planned to win the money back and put back only what he took. However, when he learns that the man the duffle bag belongs to gets an early release date from prison, Eddie has very little time to fix his mistake. Otherwise, he’ll suffer the consequences.

Scene in Molly's Game for best gambling movies post.
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