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Top 10 Gambling Movies

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Hollywood has had a fascination with gamblers and gambling subjects. Over the years there have been many movies made with a gambling theme. Some of these have become classics. Here are a few of my favorites that deal with a variety gambling topics.

1. Rounders (1998)

As a poker player this is my favorite movie. I love the portrayal of the characters. Matt Damon plays a reformed poker player who just can’t give up the game. He gets into the biggest game of his life.
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2. Casino (1995)

This movie is almost tied with Rounders as my favorite. Robert De Niro plays a character based on real-life gangster Frank "Lefty" Rosenthal and tells the story of the mobs control in Vegas.
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3. Oceans 11 (1960) Remade (2001)

The original with the Rat Pack is still the classic movie about a gang set to rob the casino. The remake and sequel, Oceans 12 are popular but I still like the original.
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4. Vegas Vacation (1997)

This is an installment of National Lampoon’s vacation series with all the usual whacky situations of the other comedies. This is my favorite gambling comedy movie. The Griswolds head off for Las Vegas, as Clark got an extra bonus for developing a food preservative. The scene with Chevy Chase playing Blackjack against the dealer played by Shawn Wallace is priceless.
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5. The Big Town (1987)

Craps players will love this movie. Matt Dillon plays a small town gambler with a gift for shooting dice, who goes to Chicago to seek his fortune.
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6. Owning Mahowny

This movie shows the darker side of gambling addiction. The story is based on a true story about a bank executive who committed the largest one man fraud in Canadian history. This is not a great movie with an entertaining story line but neither is gambling addiction in true life. The fact that it was based on a true story gives it credence and makes it worth watching.

7. The Hustler (1961)

Paul Newman and Jackie Gleason star in this ultimate gambling movie about pool hustlers. Gleason plays legendary Minnesota Fats who is challenged to a high stakes match by Fast" Eddie Felson played by Newman.
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8. Bugsy (1991)

BUGSY tells the true story of legendary New York mobster Benjamin "Bugsy" Siegel who built t he Flamingo Hotel and Casino which paved the way for the mob to take over Las Vegas.
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9. Cincinnati Kid (1965)

Steve McQueen plays a rising card shark who challenges a veteran player for the chance to be known as "The Man.". Long before Texas Hold’em Stud was the game.
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10. The Sting (1973)

When a mutual friend is killed by a mob boss, two con men, one experienced and one young seek revenge by pulling off the big con on the mob boss. Paul Newman and Robert Redford play the con men in this film that won seven Academy Awards including Best Picture.
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