Top 7 Modern Gambling Movies To Stream

Rich Migliorisi, Last Updated: June 7th, 2021 - Best NJ Online Casinos For Real Money

In recent years, gambling has become more mainstream than ever before. People have always been able to show up to a brick-and-mortar casino to put a few bucks down, but the growth of online gaming has resulted in further regulation and massive growth in the industry as a whole.

The longstanding reputation of gambling, however, is that it resides in a mysterious, often dark-seeming underworld. Throughout the history of modern cinema, quite a few films have explored this realm of inherent risk and reward, and some are more accurate depictions than others.

Here, we’re going to detail several of the best gambling movies out there, ones that we feel provide some insight into this dramatic world that many know so little about.

Top Seven Must-Watch Gambling Films 

To narrow down the subject matter and keep our collection of films from being too wide-ranging, we’ve set some parameters, starting with the fact that we’ve limited the list to just seven films.

We are not the Academy of Motion Picture Arts and Sciences, and this list is not intended to judge the cinematic merits or even what the “best” movies are. Instead, our goal is prioritizing films in which gambling plays a major role in the plot whether it be cards, casinos, or sports betting.

This is where our list varies from many of the lists that have been put out recently, along with the fact that we’ve limited the time frame to the last 25 years. For example, “Oceans 11” may be partially set in a casino but it isn’t about gambling, it’s about a robbery.

On the other side of the coin, “Rounders” is a quintessential gambling movie, where card-playing and gambling are central to the entire theme of the film.

Without any further delay, let’s get to our collection of seven must-see gambling movies.

21 (2008)

Based on the best-selling book Bringing Down The House, 21 takes you on a roller coaster of the intoxicating highs and dangerous lows of cheating the system, starring Jim Sturgess as a mathematics major at MIT and Kevin Spac

Ben (Sturgess), is recruited to join a covert blackjack team made up of his students and led by one of his professors, Micky Rosa (Spacey). The team, with Ben as its new star, travels back and forth to Las Vegas, employing card-counting techniques and an intricate system of signals in order to win millions at the tables.

But once casino security begins to catch on and his relationship with Micky begins to sour, Ben realizes the stakes are actually much higher than he ever imagined.

This is a masterclass in the process behind card-counting, making this one of the very best modern gambling movies out there. Those with an interest in blackjack would probably embrace this film about the science behind gaming the system and the perils that come along with it.

Mississippi Grind (2015)

Simply put, Mississippi Grind is another story of gambling addiction but is told in a very different way than most other films of its kind. This slow-burning tale starring Ben Mendelsohn and Ryan Reynolds takes place on the open road of middle America and might be the latter actor’s best work to date.

Gerry (Mendelsohn) is a downtrodden gambler whose luck begins to change when he meets Curtis (Reynolds), a charismatic poker player. The two men forge a friendship as they travel down the Mississippi River to various bars, pool halls, casinos, and racetracks along the way looking to make a few bucks, experiencing adventures which lead to startling highs and disparaging lows,

This film doesn’t draw you with a flashy education in the mechanics of the games they play (as 21 or Rounders do) but its somewhat relatable and extremely layered characters cause us to be invested in the exploits of these two men on the road trip of a lifetime.

Despite its grim look on the outside, Mississippi Grind has much more to offer and although this movie is not entirely about gambling (there are definitely some other themes as well), it still qualifies here.

The results of Getty and Curtis’ betting adventures relate directly to the plot of the film and the arc of the characters. If you’re looking for a film with heavy ties to gambling but also contains other significant plot points, this could definitely be one for you.

Molly’s Game (2017)

Based on a true story, Molly’s Game is the most recent gambling film on this list, as it was released in 2017.

Molly Bloom (Jessica Chastain) was an Olympic-class skier, but an injury cost her a career in the sport. She moved to Los Angeles and ran into Dean Keith (Jeremy Strong) who reveals to her the world of underground poker games. Soon enough, Molly is helping run a high-stakes poker game, which includes celebrates and Russian mobsters.

Unfortunately for Molly, she was arrested by the FBI and faced criminal charges for her past involvement with running these poker games. At this point, Molly even wrote a book detailing the events. The FBI is also trying to tie her to her the Russian mobsters at the game, but Molly claims her innocence to attorney Charlie Jaffey (Idris Elba). Charlie must decide if he wants to take Molly on as a client and help her.

Molly’s Game jumps from past and present to fill in the viewer of all the details of Molly’s life during this time, what led to it, and what is the final result.

Rounders (1998)

Released in 1998, Rounders helped spark the poker movement in the United States and is arguably the most popular gambling film in the last 25 years.

Mike McDermott (Matt Damon) is at a crossroads of sorts in his life. He gave up his love for poker and pursuit of making it a career for his girlfriend, Jo (Gretchen Mol), and instead focused on studying law. But when Mike’s friend Worm (Edward Norton) is released from prison, things begin to change and Mike’s desire to become a successful poker player returned.

Rounders then takes us on a journey with Mike and Worm as they try to grind their way to the top. But not before long, chaos ensues and what will happen to Mike and Worm’s lives comes into question. Poker players will be able to nitpick when it comes to the actual poker details, but Rounders succeeds in promoting the game, the dream, and the magic of card playing.

Two For The Money (2005)

Two For The Money is a deep dive into the mind of a high-stakes professional handicapper (Al Pacino) and former gambler, told through the story of a former athlete and his new career as a sharp sports bettor (Matthew McConaughey).

Brandon Lang (McConaughey) is a promising college football star who sustained a career-ending injury, putting his lucrative future in doubt. After excelling at a low-paying job making sports betting predictions, Walter (Pacino) notices Brandon’s penchant for picking winners and takes the young man under his wing and turns him into the newest star of his handicapping operation.

The two look to be a pretty formidable money-making team but when Brandon’s picks go cold, the dangers of illegal sports betting and the pitfalls of gambling addiction begin to rear their ugly head.

This film isn’t like 21, it doesn’t explore the mechanics of gambling or in this case, sports betting. Instead, it puts you inside the mind of a person with an addictive personality that wants to gamble more than he wants to win.

The Gambler (2014)

With a script based on 1974 classic starring James Caan, this version stars Mark Wahlberg as a bettor with no choice but to go all-in-one last time or lose it all. While the remake doesn’t come close to the original, this is an interesting character study into a self-destructive person who uses gambling as his tool. 

College professor Jim Bennett (Wahlberg) racks up massive debt and the seemingly endless displays of self-sabotage force you to question if he’s even trying to win or he’s just in it for the thrill. Things eventually reach the point where the walls begin to close in on him in the form of a well-known loan shark and the leader of an illegal betting ring, both of which he owes money to (along with a third person). 

After receiving an ultimatum, Bennett is given one last chance to raise the money needed to pay off his debt. With his life literally on the line, Jim enlists the help of his students to take a swing at one last payday and dig himself out.

Uncut Gems (2019)

Sports bettors know how difficult it can be to call it quits, whether you’re cutting your losses or capping your winnings. In Uncut Gems, Adam Sandler gets a bit more serious than usual to help deliver a cautionary tale of self-sabotage and not knowing when enough is enough.

Ratner (Sandler) is a New York City jeweler whose love for gemstones is only matched by his desire to pursue a big payday as a sports gambler. At every turn, he is looking for the home-run play that will alleviate all of his financial woes but is actually playing an incredibly high-stakes game of Russian roulette.

As Howard, who is either unaware or unconcerned with the consequences of his actions, intertwines business and his personal life, he must find a way to pay his debts before his self-destructive nature causes him to lose everything.

This film will pique the interest of sports bettors not only because of Howard’s high-stakes wagering and lifestyle, but because the narrative of the story revolves around real-life sporting events.

The film co-stars NBA legend Kevin Garnett as himself and features multiple games from the 2013 Eastern Conference semifinals. How the Safdie brothers manage to weave real games and their results into a detailed storyline that involved the star of those games himself will be an extra treat for sports fans and bettors.