15 Best Gambling Movies to Watch Over the Holidays

15 Best Gambling Movies to Watch Over the Holidays

You don’t have to be a hardcore gambler to enjoy these films. 

Below you will find a list of the best gambling movies, from all-time classics to poignant comedy-dramas.

1. The Sting

source: youtube.com
  • Released: 1973
  • Directed by: George Roy Hill
  • Starring: Paul Newman, Robert Redford, Robert Shaw
  • Gross Revenue: $156,000,000
  • Stream on: BFIPlayer (free)
  • Rent or buy on Amazon Video, Google Play, Chili, Microsoft Store, Youtube, Rakuten TV & AppleTV

This timeless classic revolves around aspiring con man Johnny Hooker (Redford) as he teams up with Henry Gondorff (Newman) and a few other con artists to scam ruthless crime boss Doyle Lonnegan (Shaw). 

One of the best grifter films, The Sting has it alla charming duo of likeable heroes, witty and highly entertaining storytelling, outstanding direction and one of the most unforgettable poker scenes ever filmed. 

No wonder it enjoyed huge commercial and critical success, getting ten Oscar nominations and winning seven, including Best Picture and Best Director.

2. Rain Man

source: youtube.com
  • Released: 1988
  • Directed by: Barry Levinson
  • Starring: Dustin Hoffman, Tom Cruise, Valeria Golino
  • Gross Revenue: $354,825,435
  • Stream on: Virgin TV Go & MGM Amazon Channel
  • Rent or buy on: Amazon Video, Sky Store, AppleTV, Google Play & Youtube

Next on our best gambling movies list is another well-known classic.

Rain Man stars car dealer Charlie Babbitt (Cruise) and the brother he never knew he had, autistic savant Raymond (Hoffman). After discovering that their father has left his $3 million estate to Raymond, Charlie checks him out of the mental institution where he is staying and takes him on a road trip that will change both their lives.  

A touching film, this comedy drama has won the hearts of critics and audiences mainly due to the masterful direction by Levinson and the exceptional performance by Hoffman. Rain Man also features one of the most recognisable casino scenes in gambling films, which see Raymond winning at blackjack thanks to his extraordinary mathematical skills. 

The highest-grossing film in 1988, Rain Man won four Oscars, including Best Picture, Best Director and Best Actor in a Leading Role. 

3. Molly’s Game

source: youtube.com
  • Released: 2017
  • Directed by: Aaron Sorkin
  • Starring: Jessica Chastain, Idris Elba, Kevin Costner
  • Gross Revenue: $53,296,424
  • Stream on: Netflix UK, Amazon Prime Video & Virgin TV Go. 
  • Rent or buy on: Chili, Sky Store, Microsoft Store, YouTube, Amazon Video, Google Play, AppleTV & Rakuten TV.

Molly’s Game is, without a doubt, one of the best poker movies out there.

Based on real events, the film tells the story of Molly Bloom (Chastain), a top-class skier whose career comes to an end due to an injury, after which she falls into running exclusive high-stakes poker games, leading to her arrest by the FBI.  

The film was lauded for its amazing performances, particularly by Jessica Chastain, and the witty, fast-paced dialogue written by Aaron Sorkin. This film also marked his directorial debut. 

4. Ocean’s Eleven

source: youtube.com
  • Released: 2001
  • Directed by: Steven Soderbergh
  • Starring: George Clooney, Brad Pitt, Julia Roberts
  • Gross Revenue: $450,717,150
  • Stream on: Netflix UK, Amazon Prime Video & Virgin TV GO
  • Rent or buy on: Amazon Video, Google Play, Chili, Microsoft Store, YouTube, AppleTV, Rakuten TV & Sky Store

Featuring a stellar cast, Ocean’s Eleven is one of the most successful and most popular Las Vegas films of all time. 

The plot revolves around Danny Ocean (Clooney) and his accomplices, who plan on robbing three of the biggest casinos in Vegas at the same time.

Ocean’s Eleven inspired two more sequels, although none of them quite lived up to the energetic and entertaining first film, which got amazing reviews from critics and the audience.

A fun bit of trivia: The cast did hit the tables off-hours (how could they not when filming in Sin City?). While it is not clear who won the most, George Clooney lost 25 hands of blackjack in a row. 

5. The Hustler

source: youtube.com
  • Released: 1961 
  • Directed by: Robert Rossen
  • Starring: Paul Newman, Jackie Gleason, Piper Laurie
  • Gross revenue: $7,600,000
  • Rent or buy on: Amazon Video, Microsoft Store, Google Play, Sky Store, AppleTV & YouTube.

One of the most iconic films about gambling, The Hustler centres around “Fast” Eddie Felson (Newman), a pool player who wants to get into professional hustling and reap the rewards that come with it. However, as he prepares to beat legendary pool player Minnesota Fats (Gleason), he ends up losing more than he bargained for. 

The film won two Academy Awards and had 7 nominations, including Best Picture and Best Actor in a Leading Role. It also inspired Martin Scorsese to create an unofficial sequel with Newman reprising his role as Felson. 

6. The Color of Money

source: youtube.com
  • Released: 1986 
  • Directed by: Martin Scorcese
  • Starring: Paul Newman, Tom Cruise, Mary Elizabeth Mastrantonio 
  • Gross Revenue: $52,293,982
  • Stream on: Disney+ & Virgin TV Go
  • Rent or buy on: Amazon Video, Google Play, Microsoft Store, YouTube, AppleTV & Sky Store

Called one of the best gambling movies of all time, The Colour of Money picks up where The Hustler left off. 

“Fast” Eddie Felson, now running a successful business in Chicago, meets a young promising pool player Vincent Lauria (Cruise), whom he tries to coach into becoming a successful hustler. Even though Felson sees much of his younger self in Vincent, the latter’s tendency to show off leads to confrontation and the two part ways, meeting later on as opponents in the Atlantic City tournament. 

The Color of Money was well-received by the audience and critics alike, getting Paul Newman his first Oscar after being nominated for the award seven times. 

7. Uncut Gems

source: youtube.com
  • Released: 2019
  • Directed by: Benny and Josh Safdie
  • Starring: Adam Sandler, Julia Fox, Idina Menzel
  • Gross Revenue: $50,023,780
  • Stream on: Netflix UK

Adam Sandler stars as Howard Ratner, a jewellery store owner, whose gambling addiction has cost him his family and has put him thousands of dollars in debt. His luck suddenly changes when a rare black opal arrives in his shop with a very keen high-profile buyer. 

Sandler got very good reviews for his performance as the charismatic, fast-talking Ratner, with some even calling this the best performance of his career. The gripping plot and the edgy, almost claustrophobic style of filmmaking were also highly rated, giving Uncut Gems a 92% approval rate on Rotten Tomatoes. 

8. Hard Eight 

source: youtube.com
  • Released: 1996
  • Directed by: Paul Thomas Anderson
  • Starring: Philip Baker Hall, John C. Reilly, Gwyneth Paltrow
  • Gross Revenue: $222,559
  • Rent or buy on: Amazon Video, Google Play, AppleTV, Microsoft Store, YouTube, Sky Store & Rakuten TV

Paul Thomas Anderson’s first feature film is a gripping story about Sydney (Hall), an experienced old gambler, and his young and unpredictable protégé John (Reilly). John thrives under Sydney’s tutelage, becoming a successful small-time professional gambler, and their father-son relationship continues until John meets Clementine (Paltrow), a cocktail waitress and occasional prostitute. 

Hard Eight may not have been a box-office success, but movie reviews were mainly positive, with the majority being impressed with the simple storytelling and the outstanding performance by Philip Baker Hall.

9. Croupier

source: youtube.com
  • Released: 1998
  • Directed by: Mike Hodges
  • Starring: Clive Owen, Nick Reding, Nicholas Ball
  • Gross Revenue: $7,120,568
  • Rent or buy on: Amazon Video & Apple TV

The plot is centred around Jack Manfred (Owen), an aspiring writer with a bleak future ahead of him. Going against his better judgment, he takes up a job as a croupier and slowly gets sucked into the casino world. As his new job starts to take a toll on his relationship and the novel he is planning on writing, a lucrative but illegal financial opportunity is presented to him. 

The release of Croupier in Great Britain went by almost unnoticed; however, the film got critical acclaim upon its release in the USA. Reviewers particularly liked Owen’s performance and the realistic portrayal of the exciting but dangerous casino world. 

10. Maverick

source: youtube.com
  • Released: 1994
  • Directed by: Richard Donner
  • Starring: Mel Gibson, Jodie Foster, James Garner
  • Gross Revenue: $183,031,272
  • Rent or buy on: Amazon Video, AppleTV, Sky Store, Google Play, Chili, Microsoft Store & YouTube

A fun and highly entertaining film, Maverick is a remake of the classic Western TV series of the same name. 

Mel Gibson stars as Bret Maverick, a conman looking to get in a huge poker game with an unbelievable payoff. However, he first needs to collect a large sum of money. 

Along with Annabelle Bransford (Foster), Maverick travels from town to town, collecting debts and getting into all sorts of trouble on the way. 

The dialogue is witty, the plot is fast-paced, and every scene is packed with humorous moments and great acting skills. The ending is also sure to take you by surprise—another reason to watch or re-watch Maverick this holiday. 

11. Rounders

source: youtube.com
  • Released: 1998
  • Directed by: John Dahl
  • Starring: Matt Damon, Edward Norton, Gretchen Mol
  • Gross Revenue: $22,912,409 
  • Rent or buy on: Chili, Microsoft Store, Rakuten TV, Amazon Video, AppleTV & Sky Store

Our protagonist is Mike McDermott (Damon), a poker player who abandons his dreams of winning the World Series Poker tournament to focus on his studies. However, once his friend Worm (Norton) gets out of prison, Mike gets sucked into the underground poker scene once again, and this time the stakes are higher. 

When it comes to the realistic representation of poker in films, Rounders ranks pretty high. This is not surprising, as one of Damon’s best friends is celebrity poker player Ben Affleck. On top of that, both Damon and Norton played at the $10,000 buy-in Texas Hold ‘Em championship event during the 1998 World Series of Poker. 

12. 21

source: youtube.com
  • Released: 2008
  • Directed by: Robert Luketic
  • Starring: Jim Sturgess, Kate Bosworth, Kevin Spacey
  • Gross Revenue: $159,808,370 
  • Stream on: Amazon Prime Video & Virgin TV Go
  • Rent or buy on: Amazon Video, AppleTV, Google Play, Chili, Microsoft Store, Youtube, Sky Store & Rakuten TV

21 is based on Bringing Down the House, the 2003 best-selling book by Ben Mezrich, which documents the true story of the MIT Blackjack team.

The plot follows Ben Campbell (Sturgess), an MIT math major, who, along with five other students, is trained by his professor Micky Rosa (Spacey) to count cards and win big at blackjack. The team then take their skills to Las Vegas casinos, where they take millions in winnings, catching the attention of casino enforcer Cole Williams (Fishburne). 

The film was well-received upon release, although there were quite a few casting controversies involved. 

13. Lucky You

source: youtube.com
  • Released: 2007
  • Directed by: Curtis Hanson
  • Starring: Eric Bana, Drew Barrymore, Robert Duvall
  • Gross Revenue: $8,461,686
  • Rent or buy on: Amazon Video, AppleTV, Google Play, Chili, Microsoft Store, Youtube, Sky Store & Rakuten TV

Eric Bana plays gifted but emotional poker player Huck Cheever as he tries to get a place in the World Series of Poker tournament. Borrowing money and even stealing from his girlfriend Billie Offer (Barrymore), Huck manages to owe almost everyone in town. To further complicate things, his father L.C. (Duvall), the only person Huck can’t beat in poker and the man he hates more than anything, shows up in Vegas in time for the tournament. 

Lucky You may not have been enjoyed by everyone, but poker players (and fans) gave this film great reviews. 

14. Mississippi Grind 

source: youtube.com
  • Released: 2015
  • Directed by: Anna Boden & RyanThat’s a Wrap!
  • Starring: Ben Mendelsohn, Ryan Reynolds
  • Gross Revenue: $422,746
  • Rent or buy on: Amazon Video, Google Play & YouTube

This film centres around Gerry (Mendelsohn), a down-on-his-luck gambling addict who meets a  young, charismatic poker player named Curtis (Reynolds). Thinking of him as a good luck charm, the duo immediately become friends, travelling to the South in hopes of making it big through poker winnings.

The bittersweet film was loved for its modern take on old-school road trip movies, as well for its effective depiction of addiction and the irreparable effect it can have on a person’s life. 

15. The Gambler

source: youtube.com
  • Released: 2014
  • Directed by: Rupert Wyatt
  • Starring: Mark Wahlberg, Jessica Lange, John Goodman
  • Gross Revenue: $39,280,992
  • Rent or buy on: Amazon Video, Chilli, Microsoft Store, YouTube, Rakuten TV, Sky Store & Google Play

The Gambler, a remake of the 1974 movie of the same name, follows Jim Bennett—a literature teacher by day, a high-stakes gambler by night. The protagonist, who is romantically involved with one of his students, ends up falling into debt due to his gambling habits, forcing him to borrow money from his mother and loan sharks offering his own life as collateral. 

The Gambler got mixed to average reviews, with many critics saying that it fell short of the James Caan original. 

Still, Wahlberg was praised for his performance as arrogant risk-taker Bennett, whose desire to self-destruct leads him deep into the dark world of match-fixing, sports betting and illegal gambling. 

That’s a Wrap!

This list of the best gambling movies comprises just some of the most amazing features that bring the thrill and excitement of casino games to life, as well as portray the dark side of the gambling world. 

Did we miss any of your favourites?

Let us know in the comments. 

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