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16 Underrated Gambling Movies Worth Betting The House On

List RulesVote up the movies worth taking a two-hour gamble on.

When you think of gambling movies, what comes to mind? Martin Scorsese's Casino, probably. Uncut Gems is a recent one, so that probably pops up, too. Bugsy, The Sting, and Ocean's Eleven are other obvious titles. These are the classics, the ones that have been widely seen and are highly regarded. You really can't go wrong with any of them. 

If you've seen all of those and are looking for something you haven't seen, the following underrated gambling movies fit the bill nicely. Despite having big stars and, in several instances, A-list directors, these films somehow didn't catch on in quite the same way. A few didn't get very wide releases, whereas others simply flew under the radar. Three or four of the titles have cult followings, yet remain relatively unknown to the public at large. What they all have in common - whether comedies or dramas - is insight into the gambling phenomenon.

Which of these underrated gambling flicks is most worth betting the house on? Vote up your favorites.

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  • Photo: Miramax

    Rounders is widely considered by gambling experts to be one of the most authentic films ever made on the topic. Gamblers love it, but general audiences never quite gelled to the movie, which only made $22 million at the box office, despite starring Matt Damon and Edward Norton. Damon's character, Mike, promises his girlfriend he'll give up poker after losing his $30,000 tuition money to a Russian gangster. He keeps that promise until old pal Worm gets out of jail. Worm has debts to settle, so Mike helps him get involved in a few games. But when those turn out to be failures, the only way Mike can help his buddy to is break the promise that he'd stay away from the tables.

    Both actors give career-highlight performances in Rounders. The excellent supporting cast includes Gretchen Mol, John Malkovich, John Turturro, and Martin Landau. The movie also offers a compelling examination of the psychology of poker players. Mike and Worm have developed ways to trick and/or read their opponents. Watching them in action - and knowing they're in grave danger if they cross the gangster - provides non-stop tension. 

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  • Did you know that Woody Harrelson, David Cross, Ray Romano, Mike Epps, Cheryl Hines, Judy Greer, Jason Alexander, and Werner Herzog made a movie together? Probably not, because The Grand earned just over $115,000 when it was released in theaters in 2007. You don't get much more under-the-radar than that. 

    The reason to see this movie is that it was created under fascinating circumstances. The story involves a bunch of gamblers taking part in a poker tournament. Each actor in the all-star cast was given a character to play, but they had to improvise their dialogue. From there, they played actual games of poker against one another, so nobody knew what the plot's outcome would be. It all depended on who won for real. This oddball structure makes The Grand compulsively watchable. You never know what's going to be said or done next, because the stars didn't either.

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  • Veteran actor Philip Baker Hall gives a tour de force performance in Hard Eight, the first film from Boogie Nights director Paul Thomas Anderson. He plays Sydney, a longtime gambler who becomes the mentor to a younger one, John (John C. Reilly). They have a good thing going until John falls for a waitress/prostitute, played by Gwyneth Paltrow. A kidnapping follows, along with a bizarre act of love that Sydney commits to protect John.

    Hard Eight is a very human story about people caught up in the seedy underworld of gambling, where desperation is the order of the day. The mentor/pupil relationship between the two men is fascinating. You might even learn a few things about gambling from Sydney, just as John does. And then there's Hall, who brings a palpable sense of weariness to the role. He creates a downtrodden man who finds a glimmer of light upon gaining a protege, only to have the darkness envelop him even further in the end. 

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  • Clive Owen landed his breakthrough role with 1998's Croupier. He's Jack, an aspiring writer who takes a job as a croupier in order to pay the bills while he waits for his writing career to take off. Seeing the daily ins and outs of working in a casino - as well as meeting the people who inhabit the place - makes him realize that the material for a great book is right under his nose. As he becomes increasingly entrenched in the lifestyle, though, Jack realizes it's taking a toll on him.

    Critics agreed that Owen is magnetic in the role. Roger Ebert wrote that the actor "doesn't give himself wholly to the action, but seems to be keeping a part of his mind outside of it, measuring and calculating." That quality helps draw us into Jack's world, showing how he's impacted by everything he observes. Elsewhere, Croupier presents a realistic depiction of life spent in front of roulette wheels and poker tables, where the promise of a big win causes people to make poor choices.

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