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Going All In on the 10 Best Gambling Movies of All Time

Going All In on the 10 Best Gambling Movies of All Time: Rounders

Rounders

Mark Wahlberg’s new movie The Gambler continues a proud cinematic tradition of murky movies based around the arguably-more-murky world of gambling (It’s actually a remake of a 1970s movie starring James Caan, meaning that it also continues the tradition of turning old movies into new). Although it boasts something that the earliest entries into the genre can’t — namely, Michael Kenneth Williams, AKA The Wire’s Omar — it might up your thirst for more of the same, in which case we’re only too willing to help. From the ‘60s up through the 2000s, men have been falling for the lure of the elusive win. Here’re some of the best examples.

THE HUSTLER (1961)
In case the title of the movie didn’t tell you enough, the title of Paul Newman’s character — “Fast Eddie” — would fill in the blanks. Smart, fast and given an appropriately downbeat ending (No spoilers), this is a must-see for anyone checking out the gambling movie genre. Imagine how different it would’ve been had Frank Sinatra been successful in his attempts to bring the original novel to the screen.


THE STING (1973)
Paul Newman again, but this time his con man is less about the pool hall hustle and more about the thrill (and the danger) of high-stakes poker. Roberts Redford and Shaw are also along for the ride, making this feel very much of its time despite its depression-era setting. It ended up cleaning up at the Academy Awards, winning Best Picture, Best Director, Best Original Screenplay, Best Costume Design, Best Art Direction, Best Editing and Best Music. Newman wasn’t even nominated for his acting.


CALIFORNIA SPLIT (1974)
A masterpiece of acting (from George Segal and Elliott Gould) and directing (Robert Altman), California Split isn’t really about the story as such; instead, it’s more a character piece about two gamblers who couldn’t get out when the going was good — although, to be fair, the going was never that good at any point during the entire movie. Think of it as a mood piece about addiction, only one that’s both enjoyable to watch and funny as hell.


RAIN MAN (1988)
Rain Man wasn’t just a movie about two brothers reconnecting as the result of unlikely circumstances (although it is that, as well); it’s a movie that taught the public two things. Firstly, that Tom Cruise could act — his Charlie Babbitt is charming, frustrating and altogether human — and secondly, that counting cards is something that’s best left to autistic men in their early 50s, especially ones that are excellent drivers. (Note: some may disagree about that second lesson.)


HARD EIGHT (1996)
If nothing else, the cast list from Paul Thomas Anderson’s early crime thriller should be enough to convince you to watch: John C. Reilly, Samuel L. Jackson and Gwyneth Paltrow, sharing a screen? (Philip Seymour Hoffman also shows up.) That they’re showing up in a neo-noir where Reilly and Philip Baker Hall play gamblers drawn into a far darker world than they’re ready for is just (the most delicious) gravy.


ROUNDERS (1998)
Apparently, high-stakes poker was so high-stakes in 1998 that is could lure both Matt Damon and Ed Norton into its web — along with John Malkovich, Famke Janssen and Martin Landau. Despite what it first looks like, this isn’t a grim noir-inspired story, however; think of it more like an inspirational sports movie with some particularly unusual participants.


LOCK, STOCK AND TWO SMOKING BARRELS (1998)
Think of this British comedy as a cautionary tale about knowing your limits. What happens when you lose a bet you can’t afford? Guy Ritchie and crew reveal all, albeit in a far more entertaining (and less dangerous) way than the reality could turn out, and with a far better soundtrack.


CROUPIER (2000)
If there’s one running theme to be found in movies about gambling, it’s this: It will take over your life. No matter who you are or what you were doing beforehand, it’ll just come in and possess every thought in your head — as demonstrated by Clive Owen’s character in this classy thriller from the turn of the century, to the point where it even screws up his relationship with Gina McKee. What was he thinking?


OWNING MAHONEY (2003)
Post-Hard Eight, Philip Seymour Hoffman returns to play the lead in this based-on-a-true-story flick about a bank employee who embezzled more than $10 million just to pay for his own gambling addiction. Worth watching just to remind yourself as the stakes get higher than this really is based on something that actually happened. Truth is not only stranger than fiction, it’s also more expensive.


21 (2008)
And talking of movies based on reality, this “math geeks beat the House because math” movie was based on the true story chronicled in the book Bringing Down the House. The movie version features more beautiful people — no offense to MIT students, but, come on: Jim Sturgess and Kate Bosworth? — and just might have ratcheted up the drama just a little bit. (Not to mention the filmmakers white-washed most of the characters, who were Asian in real life.) Enjoy it as much as you want, just remember that it should all come with a banner that screams “Don’t try this at home.”

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