Having been holed up in the bunker for over 70 days with few live sporting events to watch or bet on, I have turned to the silver screen for entertainment. Staying at home has allowed me to catch up on gambling movies I’d never seen or had not watched in many years. After taking in many films, I turned it into a ranking of the top 10 gambling films of all time. While sports are a terrific entertainment escape and a betting marketplace in which we grind out hard work and diligent handicapping, the arts are a great escape — when there is no escape.
10. The Gambler (1974, James Caan, Lauren Hutton)
Caan is a college English professor in New York who has an unhealthy desire for sports betting action and admittedly enjoys the sweat of a loss more than a windfall. He will bet on just about anything and even turns to playing pickup basketball games in the park — at one point against kids for $20 per match — to dig out of a financial hole. Eventually accumulating $44,000 in debt to bookmakers, he stoops to asking his mother for money to help bail him out. He and his girlfriend, Hutton, travel to Las Vegas, where he has a stroke of luck but soon falls back into the spiral of revolving debt. The ultimate low point comes when he asks one of his students, who is the star of the basketball team, to fix a game. The acting is borderline excellent and the cinematography is very appealing. While the story is entertaining and sometimes comical, it also paints a dark picture of a person with a serious problem.
9. Rounders (1998, Matt Damon, Edward Norton)
Another Matt Damon film that features him possessing a superior mind and talent. In “Rounders,” Damon is blessed with great skill at poker. He is a college student in New York who gambles his tuition money and loses his girlfriend and nearly his life. But the film never comes across as too dreary, as Damon’s personality and quick wit exude positivity and hope. Damon goes through escapades with a close friend, Norton, who has just been released from prison, his college professor, the Russian mob and seedy underground card rooms. Director John Dahl does a great job of forming “Rounders” into an intriguing, dramatic and enjoyable watch with a big ending.
8. Croupier (1998, Clive Owen, Gina McKee)
In this suspenseful British noir film, Owen plays struggling author Jack Manfred, whose father is a problem gambler. The father helps Owen get a job as a dealer (croupier) at a London casino to cover his costs while he continues to work on his book. While Owen does not gamble, the film takes us through his compromising positions as a croupier, being a liaison among the house, the players, his girlfriend and his fellow employees. Director Mike Hodges creates an engaging story from Owen’s lifestyle and the gamble it becomes. The film finishes with a solid and entertaining twist, and the chronology emerges as the topic for Manfred’s book.
7. A Big Hand for the Little Lady (1966, Henry Fonda, Joanne Woodward)
This movie is like many Westerns as far as setting, costumes, dialogue and characters, but it becomes a gambling movie as the gunfights are replaced with a high-stakes game of poker. It is a simple film and story with a tremendous supporting cast and a wonderfully enjoyable plot twist in the end. Fonda, his wife Woodward and their son check into a hotel after their horse-drawn carriage breaks down. While his wife attends to the repair of the carriage at a local shop, Fonda, a reformed gambler, grabs every dollar his family has and sneaks into the annual card game at the hotel with the wealthiest men in the area. Late in the game, for all of the money, Fonda falls ill, and Woodward must take his place at the table. It is a charming little tale that will put a smile on your face.
6. The Cooler (2003, William H. Macy, Alec Baldwin)
Baldwin does maybe his best acting job in this film. All the characters are so well portrayed that the story seems genuine. It never reaches the point of feeling like sensationalizing Las Vegas, good or bad, but rather a tale one can imagine as being real. Macy is “the cooler,” a casino executive who mingles with hot gamblers due to an aura of awful luck that seems to follow him and anyone he’s with. Baldwin is the old-school, break-your-kneecaps casino boss who is threatened by investors brought in to bring his place up to speed on all levels. The dynamic involving Baldwin, Macy, the love affair with Macy’s cocktail waitress girlfriend, Maria Bello, and the casino that ties them all together makes for alluring theater. And the ending is a long-awaited streak of good luck.
5. The Cincinnati Kid (1965, Steve McQueen, Ann-Margret, Edward G. Robinson, Karl Malden)
McQueen is one of my favorites, and his carefree, mysterious, astute essence of cool is on full display in a film that builds to a defining poker game pitting The Kid vs. The Man. McQueen is The Kid and is known as one of the best card players in the land. He aspires to test his skill against the best players in the world, such as The Man, played by Robinson. The story is simple and carries the usual suspects — gambling, drama, beautiful women, cigars and whiskey — but the movie is definitely one of the classics. Other works are more intricate, dramatic and creative, but the combination of this film’s adventurous quality, the illustrious cast and the bonding between McQueen and the viewer help “The Cincinnati Kid” stand the test of time.
4. Molly's Game (2017, Jessica Chastain, Idris Elba, Kevin Costner)
Based on a true story, Chastain plays Molly Bloom, who was a world-class skier but suffered a career-ending back injury in her final attempt to make the U.S. Olympic team. She ends up in an office job in Los Angeles, working for a boss who runs a high-stakes poker game for celebrities and other rich men. A law school graduate, Chastain is very sharp and innately competitive. She uses her skills to take over the operation of the poker game and turns it into a multimillion-dollar business in Los Angeles and New York. Eventually it becomes overwhelming with debt, drugs, the mob and the FBI. Chastain hires a high-priced lawyer, Elba, to represent her in what is a great story and truly a fascinating depiction of how people with elite gifts can reach the highest levels in almost any field.
3. Owning Mahowny (2003, Philip Seymour Hoffman, Minnie Driver)
Wow. Hoffman is up to his usual tricks of amazing acting in the true story of Brian Molony, a Toronto bank vice president who embezzles millions of dollars to fund a gambling addiction. In the movie, Hoffman plays Dan Mahowny, who drives a beat-up car, wears ill-fitting suits and otherwise lives a disheveled lifestyle, representing nothing close to his high-roller status in the casinos. Driver plays Mahowny’s girlfriend, who eventually discovers his sickness and offers unconditional support in trying to cure him. Director Richard Kwietniowski does a masterful job of taking a generally depressing storyline but never letting the film become such by maintaining suspense, action, highs and lows and occasional humor, presenting a captivating show.
2. The Sting (1973, Paul Newman, Robert Redford)
Winning an Oscar for best picture, “The Sting” is a joyful story of gambling, mischief, deceit, drama and adventure. Newman and Redford share the same playfulness they did in the classic “Butch Cassidy and the Sundance Kid.” Director George Roy Hill sets the movie in Chicago in the mid-1930s with great characters and costumes. The dynamic of Newman and Redford coupled with their (perceived) allies and adversaries is seductive, witty and endearing. The twists and turns of the plot come full circle in a climactic ending that induces feelings of laughter and celebration. A diverse yet simple, feel-good semi-masterpiece.
1. The Hustler (1961, Paul Newman, Jackie Gleason, George C. Scott)
Playing the role of pool shark Fast Eddie Felson, Newman delivers one of his finest performances, as do Gleason and Scott. The film is about character, inner strength, human weakness and the battle to conquer problems. The stage is pool halls, taverns, back alleys and the apartment of Newman’s alcoholic girlfriend, Piper Laurie. The gambling and the pool games are not a shot-by-shot chronology that paints the progression of the story but rather the vehicle used to depict Felson’s fight to become a confident, respected person and an eventual winner in life. A captivating and entertaining dance of a film that has the excitement of fun and games along with a much deeper underlay fueled by tremendous acting.
Others watched: “Dinner Rush,” “Casino Royale,” “McCabe and Mrs. Miller,” “Casino,” “Uncut Gems,” “California Split” and “Ocean’s Eleven” (original)