Popular Movies About Gambling

james caan in the gambler movie 1974

Movies about gambling are exciting, fun, packed with drama, and feature unusual, yet relatable characters. After all, they show how risky gambling can be even if you only play online craps, and everyone enjoys a movie that keeps you on the edge of your seat. Whether they are about childhood friends from poor neighborhoods looking for a quick and easy way to get rich, or about experienced criminals who are likable and scary at the same time – gambling movies usually provide a perfect balance of action, comedy, and drama that is hard to beat. And not to mention, many of them are based on true events, and no one writes scripts as interesting as life does.

Here are our top movies about gambling!

rounders movie with john malkevich matt damon

“Rounders” (1998)

Is “Rounders” the best movie ever? Probably not, but it is the best movie about poker! This movie, directed by John Dahl, is starring Matt Damon and Edward Norton as two childhood friends who are playing underground poker tournaments to pay off their debts. Of course, Mike (Damon) is a good guy who studies law and wants to make a decent living, while Worm (Norton) hustles through life. Once they meet again, after Worm is released from prison, Mike’s life takes an unexpected turn and he has more than his college exams to think about. “Rounders” initially received lukewarm reviews but has become a classic, especially among poker players.

“Molly’s Game” (2017)

A biographical crime drama, directed by Aaron Sorkin is based on memoirs by Molly Bloom (played by Jessica Chastain), a girl that is equally beautiful and street smart. Bloom was a professional skier, dreaming about the Olympics, but after an injury that ended her skiing career, she had to find a way to manage. The answer was – underground poker tournaments with A-list celebrities, businessmen, and sports players. And like that isn’t weird enough, there are also the FBI, and Russian mafia involved, as well as a Ponzi scheme. Keep in mind, this story is based on true events, and all the unexpected twists and turns will leave you seriously impressed by “Molly’s Game.”

uncut gems with adam sandler movie hits

“Uncut Gems” (2019)

When you think of Adam Sandler, you don’t think of serious roles, but goofy, juvenile jokes and family movies. Well, think again. “Uncut Gems” is a true gem in this movie category and is starring Sandler, as Howard Ratner, a gambling addict and a jewelry store owner, who gets into some risky business by loaning money from shady guys and equally shady family members. His big opportunity to pay off his debt comes in the form of a unique black opal, he got illegally from a mine in Ethiopia. Of course, all he needs is money to place a single bet that will change everything. Dynamic, fast-paced, and dramatic, this movie will blow your mind.

“21” (2008)

If Rounders is the ultimate poker movie, then “21” is the ultimate blackjack movie. Based on true events as described by the author Ben Mezrich, the storyline follows six talented MIT students and their professor (Kevin Spacey), trying to beat the casino while counting cards in blackjack every weekend (which is, in case you didn’t know, a practice that can get you into some serious trouble). As their relationships get more and more tense, they don’t even notice that the head of security at a popular casino venue (Lawrence Fishburne) is after them. This heist drama will keep you on the edge of your seat, thanks to amazing group dynamics, intelligent humor, and attractive, authentic locations.

“The Gambler” (1974)

Forget about the 2014 remake with Mark Wahlberg, and please watch the original! “The Gambler” is an amazing crime drama written by James Toback and directed by Karel Reisz. Based on events Toback experienced firsthand as a problem gambler, the movie tells a story about Axel Freed, a Harward professor who, as one would expect, owes a great deal of money to his bookie. What makes this movie so unique is that it focuses on reasons why people gamble, how they are perceived by society and their loved ones, and how one becomes a gambling addict in the first place. James Caan is at his 1970’s best in this film.

“Ocean’s Eleven” (2001)

Ok, we have to admit this is not a traditional movie about gambling, but let’s be real – the setting plays an important role, and it is impossible to imagine it elsewhere. This heist comedy directed by Steven Soderbergh is about a team of, you guessed, eleven criminals trying to rob not, one, not two, but three Las Vegas casinos – Bellagio, the Mirage, and the MGM Grand casinos. The ensemble cast features all the big names of the early 00s – Julia Roberts, Andy Garcia, George Clooney, Matt Damon, Brad Pitt and many more, and is one of the very few movies we can watch over and over again.