Publish: 29.05.2018

10 Classic Gambling Movies and Scenes

Gambling has always been a fascinating subject for Hollywood. Glamorous, gritty, combining the adrenaline of table play and the romance of what can happen when money and booze flow freely. A little crime, a little sex, morality tales about winners and losers, rags to riches and riches to rags – the unpredictability of gaming are endlessly attractive and compelling. Here then is our very subjective top ten list of the best classic flicks with a gambling theme. Did we miss your favourite? Let us know!

21 – This 2008 film is based on the true story of a band of brilliant MIT students whose collective memory and math powers are harnessed by professor Mickey Rosa (Kevin Spacey) to count cards and win in casino Blackjack.  The young prodigy Ben Campbell is seduced by a lovely team member (Kate Bosworth) and the allure of luxury weekends in Vegas, living the good life and raking in millions.  The casino scenes — filmed on location at Planet Hollywood, Red Rock Casino, and Hard Rock – are gripping and realistic. Things go well till the team decides to cut Mickey out of the deal. When they cross paths with casino strongman Cole (Laurence Fishburne), things spin out of control. The Spacey character is memorably played but his manipulations of the handsome young Ben are a bit creepy in view of recent allegations of paedophilia against the older actor. Trivia: one memorable phrase from the film is “Winner Winner Chicken Dinner” – the origin of the phrase was the fact that a winning bet at a Vegas casino was enough to buy the standard meal on offer.

Rain Man – The Oscar winning 1988 road trip buddy movie starring Tom Cruise and Dustin Hoffman as two estranged brothers. When sports car dealer Charlie (Cruise) learns of the death of his father, he discovers the existence of an autistic older sibling Raymond (Dustin Hoffman). Charlie discovers that Raymond has a phenomenal visual and mathematical ability, which he decides to profit from at the blackjack tables. The scenes in the casino and Las Vegas generally are spectacular, the flash and glamour set in stark contrast with Hoffman’s bewildered yet sharply focused gaze. The understated film packs an emotional punch, which led to almost universal popular acclaim.  What is less known is the fact that the movie was based on a real person, Kim Peek, whose prodigious memory enabled him to remember 12,000 books words for word. While Peek never counted cards in Vegas to our knowledge, his story did inspire Rain Man’s screenwriter and the millions who helped the movie gross $354 (£266) million. For a script turned down by producers till Barry Levinson picked it up, that turned out to be a great bet.

Honeymoon in Vegas (1992) and Indecent Proposal are different movies but both are based on one provocative premise: lending your lady to a rich old gambler in Vegas to pay off a gambling debt. The former flick is a romantic farce about a young couple, Betsy (Sarah Jessica Parker) and Jack (Nicholas Cage) off to get married in Vegas. Jack is tricked by card shark Tommy into losing all his money. Tommy, smitten by Betsy as the spittin’ image of his dead wife, agrees to forgive the debt in exchange for taking his fiancée for a weekend in Hawaii. When Betsy starts to fall in love with her creditor, Jack needs to get his act together and get his girl back.  The film has its moments: Jack sheepishly explains to Betsy that his straight flush was “like unbeatable” she memorably retorts: “’Like unbeatable’ is not unbeatable.”

Indecent Proposal came out the following year. David (Woody Harrelson) and Diana (Demi Moore) are a married couple who go to Las Vegas in hopes of winning enough money to finance a dream project. They lose their savings at the roulette table.  Ultra-wealthy John Gage (Robert Redford) offers to pay a million bucks to David for a night with his wife.  They accept his offer, and she flies off in Gage’s helicopter to his yacht. He gives her a chance to go back to her husband if he loses the flip of his coin. Gage calls “heads” correctly, and she spends the night with him. Romance develops between the two, leaving David out. In the end, John lets Diana return to her by-now-ex-husband, showing a two-headed coin and telling her she was just one in a long line of “million dollar” girls.  The film grossed $266 million and provoked millions of couples to debate what they would do if faced with a similar “offer they can’t refuse.”

The Gambler was the debut film project of James Toback, now in the news under less than complimentary circumstances. The movie, released back in 1974, is memorable as the definitive work on problem gambling. Axel Freed (James Caan) is a literature professor who has a secret. He wins big and then loses it all. In the end, he becomes indebted to loan sharks and needs to struggle for his survival. In the end, he emerges successful and kicks free of his habit. A 2014 remake with Mark Wahlberg in the lead, set in LA rather than NYC, did reasonably well at the box office, grossing $34 (£25) million, but it lacks the iconic quality of the original.

High Roller is the true-life story of Stu Ungar. In this 2003 biopic, Stuey (Michael Imperioli) goes from being a teen prodigy in playing card to become a world-famous gambling phenomenon. Gin rummy proves to be his redemption, and poker his pathway to fame and fortune. But success comes at the price of addiction and excess. A gripping film with life lessons for every punter. Trivia: Stuey first enters a Vegas casino in 1973, but the video slots on the other side of the glass doors would not be invented for another two decades.

Rounders, a 1998 American drama about underground high-stakes poker, starring Ed Norton and Matt Damon as two friends who turn to playing poker city to city to pay off a large debt. The film disappointed at the box office but it chronicles the phenomenal rise of poker – especially Texas Hold‘em – as a cultural phenomenon. Today it’s considered a cult classic especially for the supporting roles of John Malkovich as Teddy KGB and John Turturro as Joey Knish, inspired by the real-life poker legend Joel “Bagels” Rosenberg.

Honorable Mentions go out to California Split (1974) as the odd couple of Charlie (Elliott Gould) and Bill (George Segal). The two are ever in search of the ever-elusive big poker payday. Going even further back (1965) is The Cincinnati Kid, where a young Steve McQueen wants to build his reputation as the best poker player by beating the incumbent Edward G. Robinson. The big game is fixed in his favour, but the Kid wants to win it on his own skills.

A review of classic gambling moments from Hollywood would not be complete without mentioning the scene in Casablanca where Police Captain Renault blows the whistle on Rick’s Café, famously exclaiming “I am shocked – shocked! – to find gambling going on here!”  … as the croupier hands Renault a pile of money under the table.

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