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Hollywood’s 15 Greatest Gambling Movies Ever Made – Roll the Dice

Hollywood has produced some of the greatest gambling movies of all time. From classic films like The Hustler to more modern favorites like 21, these movies have captivated audiences with their thrilling stories and intense action. Whether you’re a fan of poker, blackjack, or any other form of gambling, there’s sure to be a movie on this list that will appeal to you. Here are Hollywood’s 15 Greatest Gambling Movies Ever Made.

1. The Hustler (1961)

An American drama directed by Robert Rossen and starring Paul Newman in the lead role as “Fast” Eddie Felson, a small-time pool hustler with big aspirations. Featuring unforgettable performances from Newman, Jackie Gleason, George C. Scott, and Piper Laurie, the film follows Eddie’s journey from the smoky pool halls to high-stakes tournaments as he struggles to become one of the greats.

2. The Cincinnati Kid (1965)

A classic drama from director Norman Jewison starring Steve McQueen as a young poker player looking to make his mark in a high-stakes card game. Featuring an all-star cast, including Edward G. Robinson, Ann-Margret, and Tuesday Weld, The Cincinnati Kid is a thrilling ride through the underground world of professional gamblers, filled with colorful characters and intense moments of suspense.

3. The Sting (1973)

A beloved classic crime-drama directed by George Roy Hill and starring Paul Newman and Robert Redford. Following two con men in 1930s Chicago, the story follows the pair as they attempt to dupe a gangster out of his money through an elaborate sting operation. With its clever plot twists, charming performances, and toe-tapping soundtrack, The Sting remains one of the most entertaining films ever made.

4. The Gambler (1974)

A classic crime-drama film directed by Karel Reisz and starring James Caan. The movie follows Caan as Axel Freed, a compulsive gambling addict who spirals out of control after taking on an illegal bookie while trying to pay off his debts. With its raw look at addiction and moral complexity, The Gambler is both thrilling and thought-provoking in its examination of a man’s struggle with his demons.

5. California Split (1974)

A classic comedy-drama film directed by Robert Altman and starring Elliott Gould and George Segal as two gamblers. The movie follows the pair as they embark on a gambling streak in search of the ever-elusive big payday. Along the way, they encounter heated discussions with other gamblers, two lovely prostitutes, and an unforgettable journey into the seedy world of gambling.

6. 8 Men Out (1988)

A drama based on the true story of the infamous 1919 Black Sox Scandal. Directed by John Sayles, this gripping look at America’s pastime follows eight Chicago White Sox players as they conspire with gamblers to throw the World Series of baseball in exchange for money. Featuring performances from an all-star cast, 8 Men Out captures the complexity of human nature and offers a compelling window into how greed and vanity can corrupt even those we idolize.

7. Maverick (1994)

A classic action-comedy starring Mel Gibson and Jodie Foster. The movie follows the story of Bret Maverick, a gambler who is trying to win a high-stakes poker tournament in order to pay off his debts. Maverick must rely on his wit and charm to outsmart his opponents and get what he needs. With its memorable characters, witty dialogue, and exciting action sequences, Maverick has become an iconic movie that continues to entertain audiences today.

8. Hard Eight (1996)

A crime drama written and directed by Paul Thomas Anderson. Following the story of an aging gambler (Philip Baker Hall) who takes a young man (John C. Reilly) under his wing, the movie follows the duo as they travel across Nevada and become involved in a dangerous game of chance and deceit. Featuring an all-star cast, this tense and thrilling neo-noir is sure to keep viewers on the edge of their seat.

9. Rounders (1998)

A crime drama directed by John Dahl. Matt Damon and Edward Norton star as two college friends who turn to playing cards in order to pay off a large debt incurred from the Mob. With some help from an experienced mentor, the two must outplay their opponents and stay one step ahead of their enemies. A riveting story about friendship, luck, and fate, Rounders is an enthralling ride through the underground world of high-stakes poker.

10. Ocean’s Eleven (2001)

A star-studded caper film directed by Steven Soderbergh. The movie features an all-star cast including George Clooney, Brad Pitt, Matt Damon and Julia Roberts as they attempt to pull off the ultimate heist in Las Vegas. The crew meticulously plan their daring theft of the famous casino’s vault but quickly find themselves in over their heads in this thrilling and suspenseful ride.

11. Even Money (2006)

A gripping crime drama starring Kim Basinger, Danny DeVito and Forest Whitaker. The story follows three people who all have their own personal struggles with gambling. A novelist, an ex-convict, and a casino manager each fight to regain control of their lives as they attempt to beat the odds in Las Vegas.

12. Lucky You (2007)

A romantic drama starring Eric Bana and Drew Barrymore. The film is set in Las Vegas and follows the story of Huck Cheever, a talented professional poker player trying to win enough money to compete in the World Series of Poker. Along the way, he must contend with his personal life, his father’s expectations, and his own inner demons before emerging as a true champion.

13. 21 (2008)

A thrilling drama based on real events and people. The movie stars Jim Sturgess as Ben Campbell, a talented MIT student who is recruited by his professor to join an exclusive group of students trained in card counting. They take Vegas by storm and win big at the casino tables with their knowledge of mathematics and sharp minds.

14. Mississippi Grind(2015)

A comedy-drama film starring Ryan Reynolds and Ben Mendelsohn. The story follows two compulsive gamblers, Gerry and Curtis, as they embark on a road trip through Mississippi visiting various casinos and racetracks. Along the way, they learn about friendship, addiction, regret, family, and the paths we sometimes unexpectedly find ourselves on.

15. Molly’s Game (2017)

A biographical crime drama film written and directed by Aaron Sorkin. It tells the true story of Molly Bloom, an Olympic-class skier who ran the world’s most exclusive high-stakes poker game and became an FBI target. The movie stars Jessica Chastain as Molly Bloom and features an all-star cast.

From classics like The Cincinnati Kid to modern favorites like Ocean’s 11, Hollywood has produced some truly epic gambling movies over the decades. Whether you enjoy a gritty drama or a slick heist movie, these flicks provide an intriguing blend of suspense, romance and danger. Gambling is often seen as an adrenaline rush in film, but it can also be a metaphor for high-stakes life decisions in other movies.

These 15 movies prove that no matter the genre or setting, gambling movies have captivated audiences for generations. So if you’re looking for a great flick to settle down and watch, check out one of these legendary gambling films for a thrilling ride from start to finish and If you’re looking for an exciting gambling experience without leaving the comfort of your own home, check out these best US casinos online, where you can enjoy all the thrills and spills of a real casino from the convenience of your own device.