Stream Films About Gambling (No Risk)

The Rocking Horse Winner 1949 Based on a D.H. Lawrence story. Directed by Anthony Pelissier. With Valerie Hobson, John Howard Davies, Ronald Squire, John Mills. British socialite Hester Grahame persists in spending far more than husband Richard makes. Young son Paul is aware of his mother’s unsatisfied needs. Given a rocking horse for Christmas, he shares his anxiety with handy man/former jockey Bassett who talks to him about racing. Paul’s rides on the toy become frenzied. He presses Bassett to place a small bet for him and wins.

The boy forms a syndicate with Bassett and his uncle secretly wining many thousands of pounds. He tells them his horse knows the champions. Riding feverishly garners names. Unfortunately, arranging for his mother to receive the windfall as an inheritance doesn’t solve the problem. Hester continues to spend recklessly; the syndicate begins to lose money. Paul knows he has to pick the Derby winner to fix everything. The price is extremely high. A wonderful film. Economic and strong. Rent on Amazon Prime.

Two for The Money 2005 Directed by D.J. Caruso. This one depicts the popular world of sports betting which, according to The American Gaming Association, garners $150 billion annually in the U.S. That’s billion. Ostensibly hoping to play big league football, Brandon Lang (Matthew McConaughey, completely unbelievable as a player, though fine off the field) suffers an injury taking him out of the game. He drifts into handicapping sports at a 900 call-in number for $12 an hour, quickly earning a reputation for unerring accuracy.

Brandon receives a job offer from Walter Abrams (Al Pacino), owner of the largest sports “consultancy” in the country and flies to New York.  His new boss knows a natural gift when he sees it and brings Brandon along with tough love and perks until he becomes cable television’s smooth-talking John Anthony, the greatest money-earner on staff, and like family to Walter and his wife Toni (Rene Russo). That the young man doesn’t gamble, drink, do drugs and works out (in an effort to get back into football shape) is almost insurance. The whole thing takes Brandon by surprise.

Buoyed by his mentor, the new hot-shot’s ego swells so much he doesn’t fully take in risks implicit in the boss’s manipulation. Disillusionment affects performance. Walter has a weak heart and an up-till-then-held-in-abeyance gambling problem. He’s also self-destructive in ways that will affect them all. Pacino is terrific, the story gripping. Scenes of watching games on which the firm’s future rests are as heady as any depiction of Wall Street. Rent on Amazon Prime.

The Cooler 2003 Directed by Wayne Kramer. In gambling parlance, a casino “cooler” is an unlucky individual, usually a casino employee, whose mere presence at the gambling tables usually results in a streak of bad luck for the other players. Former gambling addict Bernie Lootz (a wonderful William H. Macy) has promised to act as a “cooler” at the Shangri-La Casino for six years in exchange for having debts paid off by owner Sheldon “Shelly” Kaplow (Alec Baldwin) – who incidentally broke a knee cap to stop him. Down, out, and depressed (imagine a human Eeyore) he does his job well.

Bernie rescues Natalie (Maria Bello), a waitress on whom he has a crush, from an aggressive customer. She begins to look at him differently and they date, instilling the first confidence he’s experienced in years, while simultaneously affecting his ability to spread bad luck. With indentured servitude almost up, Bernie tells Natalie his plan to leave Las Vegas. Having been paid off by Shelly, she says she won’t go, once again making him an effective cooler.

Natalie has fallen in love, however, which complicates things. Futher complication arrives in the form of Bernie’s estranged son and daughter-in-low trying to ‘take” the casino. There’s strong-arm violence, but vengeance and miscommunication provide a more or less positive outcome. A very different look at the mechanisms of casinos. Rent on Amazon Prime.

High Roller: The Stu Unger Story 2003 Directed by A.W. Vidmer. The true history of card prodigy Stu Unger who still holds the record for three Main Event wins at The World Series of Poker – the last, a year before his death from drugs and alcohol at the age of 45. As told in flashback to a man in shadows (death), Stu Unger (perfectly cast Michael Imperioli) grows up the son of a bookie. Preternatural instincts about card playing place him in games with pots of thousands of dollars at age 12. Stu blows $3,000 of Bar Mitzvah money gifted by his father’s gangster friends at the track.

Under the mentorship of Vincent (Michael Nouri), he’s floated/backed by those higher up and grows increasingly cocky. Through non-card risks, Unger also accrues considerable debt for which his life is threatened. The addict marries, lives high, moves to Las Vegas, wins his first two tournaments, has a daughter, acquires cocaine and prostitute habits, and neglects his family who eventually leave. Stu’s third big win, a comeback, happens too late. A helluva look at insidious addiction. Rent on Amazon Prime.

Mississippi Grind 2015 Written and directed by Anna Boden and Ryan Fleck. Gerry (Ben Mendelsohn) is a struggling real estate agent and gambling addict who listens to recordings about “tells” in his car (physical tip-offs as to another player’s confidence). He long ago lost his wife and child to the unbreakable habit and currently owes money to the wrong people.

Curtis (Ryan Reynolds), something of an educated cipher, seems to be drifting down to New Orleans more interested in the trip and people he inevitably charms than his destination. He intermittently gambles for pocket cash. “I win because I don’t care about the money.”

The men meet in Iowa, drink, and decide to travel together. In exchange for Gerry driving his car, Curtis will stake his companion’s gambling to the tune of $2,000. It’s an unlikely, but oddly credible friendship. We watch the men wend their way towards Crescent City revealing personalities and situations with deft timing.

Experience ranges from getting beat up to comped suites at casinos, from local interaction to respective reconnection with an ex-wife and distanced girlfriend, from last dollars, to windfall. It works. The film is low key and entertaining. Both actors are companionable. Rent on Amazon Prime.

Molly’s Game 2017 Based on Molly’s Game: The True Story of the 26-Year-Old Woman Behind the Most Exclusive, High-Stakes Underground Poker Game in the World  by Molly Bloom. Written and Directed by Aaron Sorkin. When world class skier Molly Bloom (Jessica Chastain) is injured, she gives up Olympic aspirations and moves to Los Angeles to regroup. In swift succession, the smart, attractive young woman goes from waitressing bottle service to running underground poker games for an unsuccessful real estate developer.

As she becomes increasingly popular to celebrated players, her boss feels threatened and fires Molly. She briefly runs her own game in Los Angeles, then sets up in New York. Hostesses are beautiful and well treated, games are clean, amenities high quality. Molly even tries to stop a man or two from ruining himself. Fearful of not being able to cover losses, she’s convinced by her dealer to start taking a percentage. This makes the games illegal. When a player is arrested for a Ponzi scheme, the FBI investigates her business.

Molly turns to drugs, both Russian and Italian Mafia muscle in, her assets are seized, she goes home to mom. Two years later, having written a book about what occurred, Molly is arrested by the FBI for illegal gambling in league with the Mafia. She hires high profile, skeptical lawyer Charlie Jaffey (Idris Elba), but refuses to plea bargain by naming names in order to protect the innocent. Astonishingly, it all comes right in the end. A fascinating story. Well played; one of Aaron Sorkin’s remarkable scripts. Also with Kevin Costner. Rent on Amazon Prime.

Ocean’s Eleven 2001, Ocean’s Twelve 2004, Ocean’s Thirteen 2007 Based on the 1960 “Rat Pack” film. Danny Ocean and his clever, criminal cronies carefully wreak havoc/pull off huge, complex Las Vegas casino robberies for revenge, profit, and fun. With George Clooney, Brad Pitt, Matt Damon, Don Cheadle, Andy Garcia, Bernie Mac, Julia Roberts and additional cast in sequels. Stylish thievery. Yes, there’s some violence in each. Rent on Amazon Prime.

Top photo: Bigstock

About Alix Cohen (816 Articles)
Alix Cohen is the recipient of eight New York Press Club Awards for work published on this venue. Her writing history began with poetry, segued into lyrics and took a commercial detour while holding executive positions in product development, merchandising, and design. A cultural sponge, she now turns her diverse personal and professional background to authoring pieces about culture/the arts with particular interest in artists/performers and entrepreneurs. Theater, music, art/design are lifelong areas of study and passion. She is a voting member of Drama Desk and Drama League. Alix’s professional experience in women’s fashion fuels writing in that area. Besides Woman Around Town, the journalist writes for Cabaret Scenes, Broadway World, and Theater Pizzazz. Additional pieces have been published by The New York Post, The National Observer’s Playground Magazine, Pasadena Magazine, Times Square Chronicles, and ifashionnetwork. She lives in Manhattan. Of course.