Top 4 Gambling Movies of All Time

In difference to the casino movies, we’re going to focus on movies with more of an outlook on the concept of gambling. These movies may still have major sections that take place in casinos. However, the casinos themselves are not the main focus of the films.

Without further ado, here are our top four gambling movies of all time.

4. 21 (2008) dir. Robert Luketic

Gambling movies don’t get more true to their name than with this movie.

21 didn’t receive much critical acclaim upon release, registering a 48 Metacritic score and a mere 36% on Rotten Tomatoes.

However, we here at Stake perceive this movie as something more than what critics believe it to be. Yes, there are section of this movie that drag it down.

The film can be slightly over the top or melodramatic, which takes the movie out of the realms of reality from time to time.

Jim Sturgess is, for the most part a competent protagonist with some great moments in the movie. Despite that, there are some sections where his character becomes hard to support and whilst the script is partly to blame, he is also somewhat responsible.

Kevin Spacey and Laurence Fishburne play two very compelling characters. They have ulterior motives that are revealed in the latter stages of the film, enhancing their already fantastic performances.

However, the best aspects to this movie take place in the Vegas casinos. The scenes in which these characters play the game of blackjack and win by nefarious means add a whole new dimension to the plot. You know their motivations are good, but you’re conflicted due to their means.

The ending of this movie also ties everything up well. Some may say that it’s too safe of an ending, but it satisfies well enough.

The final frames depicting Sturgess’ character explaining the movie to his scholarship director leave a positive final mark on what is a sleeper hit.

3. Rounders (1998) dir. John Dahl

Rounders, despite being revered as one of the greatest poker movies of all time, has similar downfalls to 21.

An often over the top gambling movie, Rounders does one thing differently to 21. It understands the silly nature of some of its scenes and embraces it.

Whilst the film is by no means comedic, it doesn’t get bogged down in melodrama. It walks the fine line well enough and is a superb movie.

Matt Damon shines as Mike McDermott, an up-and-coming poker player who’s caught bad strokes of luck. The film actually starts with McDermott hitting rock-bottom, doing away with classic movie stereotypes to create something wholly different.

Edward Norton plays McDermott’s slightly unhinged friend, making for some compelling character work. You know he wants to help Mike, but his methods leave you conflicted.

John Malkovich makes a great villain, hamming it up for the audience (in a good way) whilst also maintaining a level of respectability. We see a great character moment at the end of his and McDermott’s heads up, winner takes all game. The scene in which McDermott exacts revenge on KGB (Malkovich) is alone worth the watch.

Through some great performances and an intriguing script, Rounders manages to capture the essence of poker without having to litter the movie with poker scenes.

2. Molly’s Game (2017) dir. Aaron Sorkin

From the writer of the Social Network, Moneyball and popular TV shows the West Wing and the Newsroom, Molly’s Game is another feather in Aaron Sorkin’s large cap.

This gambling movie only made a touch under $60 million at the box office. A low number considering many movies with top tier casts such as this one can make over $500 million.

Despite its poor box office performance, Molly’s Game still stands as a must watch for anyone with an interest in the gambling world.

Jessica Chastain is fantastic as Molly Bloom, a former Olympic skier whose career came to a screeching halt after an injury.

Although the movie is extremely entertaining for a drama, it also addresses the important issue of gambling responsibly. Gambling addictions are present across the globe and despite it not being the main message of the movie, the issue is handled well.

That is down to an excellent script from Sorkin, whose resume precedes him. He has won an Oscar before in his work on the critically acclaimed Social Network and he was nominated for this movie as well as 2012 baseball classic Moneyball.

With a pen and paper, Sorkin can create magic and he did just that with Molly’s Game. He also showed extreme competence behind the camera as director.

We won’t go too deep into the plot of this movie as we feel we’d be doing you all an injustice if you haven’t seen it yet.

But we couldn’t recommend it any higher. An underrated masterpiece.

1. Uncut Gems (2019) dir. Safdie Brothers

One of the best movies to come out of last year, Uncut Gems was loved by fans and critics alike upon release.

Unfortunately, the news struggled to spread across the world with most screenings taking place in the US. It’s a real shame too, considering just how good this gambling movie is.

Adam Sandler is terrific as Howard Ratner, a jeweller with a bad gambling addiction. He is well supported by a string of actors.

Newcomer Julia Fox, Lakeith Stanfield (Get Out and Knives Out), Idina Menzel (Frozen), Pom Klementieff (Avengers: Endgame) and Judd Hirsch (Serpico and Independence Day) all provide excellent performances.

However, one performance that does not get enough attention is that of former NBA star Kevin Garnett. Portraying himself, the former Boston Celtic and NBA champion takes the stereotype that sports stars can’t act and throws it out the window.

The plot is simple. Ratner (Sandler) needs to retrieve an expensive gem in order to pay off all of his debts. We won’t give any more information on the synopsis than that.

Sandler, whose career has been filled with lacklustre comedies ever since his Golden Globe-nominated performance in 2002 ‘rom-com’ Punch-Drunk Love gives his best ever performance as Ratner.

It left many clamoring for him to receive a nomination at the Academy Awards. Something which never eventuated. However, despite the movie’s lack of recognition, there is no doubt that it is a bonafide smash-hit that deserves more attention.

If you haven’t seen this movie yet, do yourself a massive favour and watch it. There is hardly a foot put wrong all movie and it will entertain you from start to finish.

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