Top 10 Movies About or Set in the World of Gambling

The World Series of Poker is in full swing in Las Vegas as I write this and its popularity is rising with each passing year. ESPN shows the tournament ad nauseum through the course of the year and people continue to tune into it episode after episode and will likely do so when the new tournament is shown later this summer.In the spirit of the topic I thought it would be fun to pick the 10 best movies either about gambling or set in the gambling world that are worth checking out. Often times the poker played in these films is the stuff of pipe dreams with winning hands beating sometimes near unbeatable hands. The last James Bond film, Casino Royale, ended with a poker hand in which the fourth or fifth best hand is something a commoner like you or me would dream of. The odds of this actually happening are greater then winning the lottery or getting struck by lightning but, hey, it’s the movies so we go with it.

Before I start I wanted to list the absolute worst gambling film ever made:

FEVER PITCH (1985 – Director: Richard Brooks) – Not to be confused with the funny Jimmy Fallon baseball comedy of a few years ago, this dud was the cinematic swan song of writer/director Richard Brooks who crafted out a long and successful career with such movies as Cat on a Hot Tin Roof, Blackboard Jungle, Elmer Gantry, The Professionals, and In Cold Blood. Brooks’ script pretends to know something about gambling but it becomes painfully clear almost right away that the movie doesn’t know a thing. Ryan O’Neal stars as a newspaper writer who does a column about his gambling addictions under an assumed name. When O’Neal gets in too deep with some “bad men” he goes into rehab and writes about that. Now I am going to ruin the ending for you so you never even attempt to seek this garbage out. O’Neal, who still owes thousands of dollars to bookies, has completed his rehab. He goes to the airport to head home and when he gets there he fishes out his last coin and sticks it in the nearest slot machine. Lo and behold O’Neal hits the jackpot which will now get him out of debt and he will live happily ever after. This ending is condescending and insulting to the viewer. Can you imagine what any hopelessly addicted gambling addict must have thought after seeing it? Do you think this may have been another crutch, another hope to lean on? The film is a cheat. Audiences were rightly laughing at this pile of junk and it wisely is long forgotten.

Here is my choice for the 10 best gambling related movies. As usual they are listed not by preference but in alphabetical order.

BUGSY (1991 – Director: Barry Levinson) – Warren Beatty gives one of his best performances as Ben ‘Bugsy’ Siegel, the foul tempered gangster who created the idea of building a casino in the desert known as Las Vegas. Annette Bening, Harvey Keitel, Ben Kingsley and Elliot Gould co-star in this fabulous bio of a womanizer, dreamer and killer whose very dreams would result in his ultimate downfall.

CALIFORNIA SPLIT (1974 – Director: Robert Altman) – George Segal stars as a down on his luck gambler who meets high spirited and fellow gambler Elliot Gould and the two head out for drinking and gambling binges. Director Altman shows us that the gambler is less concerned with the win but with the feeling of the gamble itself. Along the way Segal nearly loses his possessions, his job and his life after being robbed. Altman wisely has an ‘up in the air’ ending with a simple shot of a spinning wheel.

THE CINCINNATI KID (1965 – Director: Norman Jewison) – Set in the 1930’s, Steve McQueen stars in the title role as a tough up and coming stud poker player who likes to travel from place to place to play in big tournaments. In New Orleans he comes to play Lancey Howard (Edward G. Robinson), the legendary stud poker player the Kid looks to unseat as the best. Karl Malden, Tuesday Weld, Ann-Margret, Joan Blondell, Jack Weston and Cab Calloway co-star in this tense drama which ends with a heads up match between the novice and the pro. This is one of those films where the final end is too ridiculous to believe but you are so caught up in it, it really doesn’t matter.

THE COOLER (2003 – Director: Wayne Kramer) – William H. Macy stars as a casino “cooler,” a man so unlucky that he simply has to stand next to a winner and his luck immediately changes. Soon he falls in love with a cocktail waitress (Maria Bello) and suddenly his luck begins to change for the better. This is bad news to the casino manager (Alec Baldwin) who hates seeing winners in his place and plots to break the two up. This is a sometimes violent, funny, sexy drama with terrific performances by the three leads.

THE GAMBLER (1974 – Director: Karel Reisz) – One of the definitive movies on gambling addiction stars James Caan as a literature professor who keeps getting deeper in debt simply because he loves the sick thrill of the bet and the rush in awaiting the results. As he goes deeper he begins borrowing money from his mother and girlfriend before driving a wedge between him and them and then has to turn to more seedy characters which put his life in danger. Despite all of this he can’t shake the feelings it gives him pushing him on a downward spiral. This is a powerful story realistically told with Caan giving a strong performance in the lead and model turned actress Lauren Hutton doing a nice job as the girlfriend. This is a film for anyone trying to kick a gambling habit or for those who don’t quite understand the addiction.

HARD EIGHT (1996 – Director: Paul Thomas Anderson) – Before Boogie Nights and Magnolia, writer/director Paul Thomas Anderson made this little seen gem originally titled (and the title Anderson still refers to) Sydney. The studio insisted on a different title and came up with a dice term that few outside the world of gambling understood. In the film Phillip Baker Hall stars as Sydney, a longtime successful gambler who, as the movie opens, sees John (John C. Reilly) sitting outside a diner looking morose. Sydney invites him in and soon takes John under his wing. Before he knows it John is being taught how to get free rooms at the top hotels without losing money and soon becomes a professional gambler, though on a lower level then the more successful Sydney. John also falls for a hooker (Gwyneth Paltrow) which leads them down a dark road with a sinister pimp (Samuel L. Jackson). Anderson shows with this early effort his great gift of crafting interesting characters into situations beyond anything they ever dreamed of, whether they like it or not. This may not rank quite as highly as Boogie Nights or Magnolia but it’s a good piece of filmmaking that deserves to be seen.

LOOKIN TO GET OUT (1982 – Director: Hal Ashby) – Jon Voight conceived the idea, co-wrote the script and stars in this drama about two small time losers who get in way over their head in New York and foolishly run to Las Vegas hoping to change their luck and hit the “big one.” While there Voight runs into his ex-wife (Ann-Margret), now a high class call girl. Director Ashby (The Last Detail; Shampoo; Coming Home; Being There) had the film taken away from him because of his unreliability due to his drug use and the film sat on the shelf for almost two years before it was quietly released and soon disappeared. While there is no way of knowing how much better Ashby’s version would have been, I can say is that this is a very entertaining drama that stretches credibility only near the end and features three strong performances from its leads.

LUCKY YOU (2007 – Director: Curtis Hanson) – This is yet another film that the studio shelved for well over a year despite the track record of director Hanson (L.A. Confidential; 8 Mile; Wonder Boys; In Her Shoes). Eric Bana stars as a full time gambler whose dream is to win the World Series of Poker. Soon he falls in love with a friend’s sister (Drew Barrymore) and his estranged father (Robert Duvall), a great poker player himself, re-enters his life. This is a straightforward drama which takes a realistic look at the world of gambling and doesn’t succumb to the perils of the “silly last hand” in the final scenes. It fared poorly at the box office earlier this year but deserves to be seen.

OWNING MAHONEY (2003 – Director: Richard Kwietniowski) – Phillip Seymour Hoffman stars in this little seen but powerful independent drama about a successful Canadian banker who, in the eyes of his friends and loved ones was a hard working, honest and loyal worker. What no one knew was that he orchestrated and pulled off the biggest fraud in Canadian banking history to support his out of control gambling habit. Hoffman offers up one of his best performances to date as a soulless, lost man who will do anything for another chance to win.

ROUNDERS (1998 – Director: John Dahl) – Perhaps the most recognizable movie about gambling, this is a film that has grown in popularity through the years and continues to get more popular just like poker itself. Matt Damon stars as a young gambler who, as the movie opens, loses his life savings to professional gambler John Malkovich in an underground club Malkovich owns. Damon decides to hang it up and go back to school and live with his girlfriend and all is well until old school buddy Edward Norton is paroled from jail and takes Damon back on an odyssey of gambling because of debts Norton incurred before he was jailed. Before he knows it Damon is skipping his personal responsibilities after the gambling bug bites him again. This is an involving drama with Norton’s character of a hopeless addict waiting for the next score and then blowing it all, not caring who he takes down with him, one of the most realistic in this type film I have ever seen. Malkovich is over the top but memorable as a Russian foe eager to take anyone sucker’s money that comes to him. The supporting cast includes Gretchen Mol, John Turturro, Famke Janssen and Martin Landau all giving good performances.

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