The Greatest Blackjack Wins on Film

It’s always tense and exciting when money is on the table, whether you’re at the casino or watching your favourite on-screen character play. Casinos and gambling have long been popular in Hollywood, and there are numerous films with iconic gambling scenes.

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While poker is undoubtedly Hollywood’s darling of the gambling world, blackjack is also a firm favourite, and the game has inspired some of the world’s best film scenes. 

The Hangover

You’ve probably seen the hilarious movie The Hangover if you play online slots, blackjack, or poker. The Hangover demonstrates that gambling scenes do not always have to be serious. A three-minute scene in the film where Alan tries to win at the blackjack table is hilarious. He has told the rest of the group that he has read blackjack books and will try to make the $80,000 they need to pay off all of their debt. This scene is so entertaining because it shows Alan in an unusually intense mood while a random equation graphic floats above his head.

Rain Man

Rain Man is one of the most iconic gambling movies of all time, with a memorable blackjack scene in the 1988 film. This scene’s emotions are conflicting because it’s both tense and rewarding, but there’s also the sense that Charlie is counting cards with his autistic brother Raymond. Charlie needs to win the game to pay off his debts, and he wins over $86,000 in this intense and dramatic scene.

License to Kill

No one enjoys live casino games more than James Bond himself. While poker is 007’s preferred game, there is an iconic blackjack win in Licence to Kill. Bond challenges the casino’s owner to a spectacular game of blackjack worth £250,000. It’s a beautifully shot sequence, and Bond, ever relaxed, beats the casino owner to the money.


This 2008 film, based on the true story of the MIT Blackjack Team, thrills around every corner. The entire film is centred on the morale and ethics of card counting and other aspects of land-based casinos. It’s impossible to pick a single scene from this film because every time the team enters a casino and walks out with a win is an event in and of itself. Every blackjack game in this film raises the stakes.

Austin Powers: International Man of Mystery

Who doesn’t enjoy the Austin Powers films? And the first Austin Powers film includes a hilarious blackjack scene. The scene begins when Number Two (Robert Wagner) refuses to listen to the dealer’s advice and hits on 17. The dealer is unaware that Number Two has X-ray vision through his eye patch and can see the next card.

One Flew Over the Cuckoo’s Nest

The film One Flew Over the Cuckoo’s Nest, starring Jack Nicholson, is unquestionably a cult classic. The 1975 film was a worldwide success, and the one scene involving blackjack is extremely touching. Randle McMurphy (Nicholson) persuades the other patients at a mental hospital to play blackjack in the scene. While the game itself was probably not one of the best wins of all time, the scene demonstrated that it is a game for people from all walks of life, which is a win in our book.

History of Blackjack

Vegas Vacation

Vegas Vacation is the fourth film in the Vacation film series, and it is about gambling in Las Vegas. The scene in question involves a significant loss and an endearing victory. Clark, the main character, loses $22,000 at the blackjack table, but at the scene’s climax, when he is down to his last two dollars, a new friend hands him a winning ticket.

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