10 of the Greatest Movies About Gamblers

Whether you believe gambling is simply a harmless and enjoyable pastime or a dangerous and debilitating addiction, there is no question that there have been some great films made about the world of gambling. Here are ten movies about gamblers that have received a high aggregate critical rating from the critics at Rotten Tomatoes or a “Certified Fresh” seal of approval. Films are listed in order of their critical ranking, from lowest to highest.

10. The Cooler (2003)

This Wayne Kramer-directed film about a perennial loser currently has a 77% “Certified Fresh” seal of approval from the critics at Rotten Tomatoes. In the film, Bernie Lootz (William H. Macy) is so unlucky at gambling that a casino he is in debt to hires him as a so-called “cooler” — someone who is supposed to sit near high rollers in the hopes of jinxing their winning streak.

While the strategy appears to work at first, Lootz’s luck begins to change after he meets cocktail waitress Natalie (Maria Bello), to the consternation of casino boss Shelly Kaplow (Alec Baldwin). Besides garnering numerous critical accolades when it was released, The Cooler also secured Baldwin an Academy Award nomination for Best Actor in a Supporting Role.

9. Owning Mahowny (2003)

A man’s self-destructive addiction to gambling is the focus of this Richard Kwietniowski-directed movie. In the film, assistant bank manager Brian Mahowny (Philip Seymour Hoffman) skims millions of dollars from his employer in order to feed his compulsive gambling habit. John Hurt costars as an unscrupulous Las Vegas casino manager, while Minnie Driver plays Mahowney’s unwitting girlfriend.

While it may seem unbelievable that a lowly assistant bank manager could ever pull off such a large-scale fraud, the events in Owning Mahowny are based on an actual theft committed by a Toronto bank employee. Owning Mahowny currently has a 79% “Certified Fresh” rating from the critics at Rotten Tomatoes who noted that “This story of addiction may lack the typical flash and glamour, but Hoffman makes Mahowny compelling.”

8. Casino (1995)

Most movies about gambling focus on the players who are trying beat the odds. However, this Martin Scorsese-directed film focuses on a character that sets the odds. In the film, talented bookmaker Sam “Ace” Rothstein (Robert De Niro) is hired by the Italian Mafia to manage the operations of a Las Vegas casino. While the arrangement works smoothly for a while, Rothstein’s fateful marriage to drug-addicted hustler Ginger (Sharon Stone) and the increasingly reckless actions of violent Mafia underboss Nicky Santoro (Joe Pesci) eventually leads to a spectacular downfall.

Casino was well received by most critics and garnered a Best Actress in a Leading Role Academy Award nomination for Sharon Stone. The film currently has an 80% “Certified Fresh” rating from the critics at Rotten Tomatoes.

7. Hard Eight (1996)

Before gaining fame with films like Boogie Nights and The Master, Paul Thomas Anderson made his directorial debut with this film about a veteran gambler. In the film, a street-smart gambler named Sydney (Phillip Baker Hall) offers to show John (John C. Reilly) — a down and out loser — how to make money gambling in casinos. After a few years of success, Sydney’s relationship with his protégé is complicated when John falls in love with Clementine (Gwyneth Paltrow), a cocktail waitress and part-time prostitute. The impressive cast also includes Philip Seymour Hoffman and Samuel L. Jackson.

“Movies like ‘Hard Eight’ remind me of what original, compelling characters the movies can sometimes give us,” wrote Roger Ebert in his review of the film. Although it lacks the “Certified Fresh” seal, Hard Eight currently has an 83% approval rating from the critics at Rotten Tomatoes.

6. The Color of Money (1986)

Made over 20 years after the original, this Martin Scorsese film continues the story of the “Fast” Eddie Felson (Paul Newman) character that was introduced in 1961’s The Hustler. However, this time Eddie is the veteran gambler, while Vincent Lauria (Tom Cruise) is the up-and-coming pool hustler. In the film, the world-wise Eddie teams up with Vincent and his girlfriend Carmen (Mary Elizabeth Mastrantonio) in order to show them the ins and outs of pool hustling. But after losing money to another hustler (Forest Whitaker), “Fast” Eddie begins training in order to take on Vincent himself in a professional pool tournament.

While some film reviewers noted that The Color of Money was inferior to The Hustler, the film garnered multiple Academy Award nominations, as well as a Best Actor in a Leading Role Oscar for Newman. The Color of Money also has a 90% approval rating from the critics at Rotten Tomatoes, although it fell short of the number of reviews required for a “Certified Fresh” seal.

5. Rain Man (1988)

While this drama film is mostly about a self-absorbed yuppie reconnecting with his long-lost brother, one of the key scenes in the film involves gambling. In the film, Charlie Babbitt (Tom Cruise) embarks on a cross-country road trip with his autistic brother Raymond (Dustin Hoffman), who recently inherited the bulk of their dead father’s estate. After discovering that Raymond has preternatural mathematical abilities, Charlie takes his brother to Las Vegas to try to beat the casinos at their own game with a blackjack card-counting scheme.

Rain Man was positively received by most critics and garnered four Academy Awards in 1989, including a Best Actor in a Leading Role Oscar for Dustin Hoffman. The film currently has a 90% “Certified Fresh” rating from the critics at Rotten Tomatoes.

4. The Sting (1973)

Set in 1930s Chicago, this George Roy Hill-directed film tells the story of a group of con men that devise an elaborate horserace betting scam in order to get vengeance on a crime boss. Besides executing the off-track horserace betting con, the characters in The Sting also participate in numerous other gambling activities, such as roulette and poker. The film’s impressive all-star cast includes Paul Newman, Robert Redford, Robert Earl Jones, and Robert Shaw.

The Sting was universally acclaimed by the critics and dominated the 1974 Academy Awards with seven wins, including Best Picture and Best Director. The Sting has also maintained its status over the years and currently has a 92% “Certified Fresh” rating from the critics at Rotten Tomatoes. While The Sting inspired 1983’s The Sting II, the sequel was not as highly acclaimed as the original.

3. House of Games (1987)

Renowned playwright and screenwriter David Mamet made his directorial debut with this film about a psychiatrist who gets caught up in the world of underground gambling and con games. In the film, psychiatrist Margaret Ford (Lindsay Crouse) is lured to a high-stakes poker game by a patient who is a compulsive gambler. Although the game turns out to be a ruse to steal her money, Margaret becomes enamored with con man (Joe Mantegna) and soon becomes entangled in one of his double-crossing schemes.

“Usually the screenwriter is insane to think he can direct a movie,” wrote Roger Ebert. “Not this time. ‘House of Games’ never steps wrong from beginning to end, and it is one of this year’s best films.” House of Games currently has a 96% approval rating from the critics at Rotten Tomatoes.

2. Croupier (2000)

A struggling writer gets an insider’s view of London’s casinos in this neo-noir film directed by Mike Hodges. In the film, Jack Manfred (Clive Owen) takes a job as a croupier in order to support himself as he writes a book. Although Jack is well aware of the dangers of gambling, against his better judgment he becomes involved in a risky scheme to cheat the casino.

Croupier was well received by many critics, including Roger Ebert, who noted that the film’s sets were “a convincing portrayal of one of those smaller London operations where the plush and the gilt and the tuxedos on the gorillas at the door don’t quite cover the tarnish.” The critics at Rotten Tomatoes gave Croupier a stellar 98% “Certified Fresh” rating and called it a “cool-headed and slick thriller.”

1. The Hustler (1961)

Paul Newman first portrayed amoral pool hustler “Fast” Eddie Felson in this Academy Award-winning film directed by Robert Rossen. In the film, Eddie makes small bets against various other small-time players before taking on and losing to champion billiards player Minnesota Fats (Jackie Gleason).  However, Eddie remains obsessed with winning, and after falling in with veteran gambler Bert Gordon (George C. Scott) and lonely alcoholic Sarah (Piper Laurie), Eddie takes another shot at Minnesota Fats.

Critics at Rotten Tomatoes called The Hustler a “dark, morally complex tale of redemption” and gave the film a 98% “Certified Fresh” rating. Besides winning two Oscars for Best Cinematography Black-and-White and Best Art Direction-Set Decoration Black-and-White, The Hustler was also nominated in seven additional categories. Newman later reprised his role as “Fast” Eddie in another critically acclaimed film, 1986’s The Color of Money, directed by Martin Scorsese.

All movie cast, crew, and awards information courtesy of IMDb.

Follow Nathanael on Twitter @ArnoldEtan_WSCS

More from Entertainment Cheat Sheet: