Make no mistake – this covers a broad range of gambling-related themes ranging from hustling to casino gambling. Nevertheless, they have all been box office hits in more ways than one or just a ‘good movie’ to some. In fact, some of them can be termed the flashiest and most memorable flicks ever made.
So without further ado, let’s get down to the top 5 that make it to our list.
The Gambler – 1974
No one needs a hint to figure out what this movie is about. This is a crime drama that fetched the inimitable James Caan a Golden Globe nomination for his performance. It is one movie that gambling purists could easily identify with. Caan plays the role of Axel Freed, a New York City Harvard University professor who becomes a reckless gambler deep in debt. At college he is a source of inspiration for his students as he discusses Russian novelist Fyodor Dostoevsky’s works on psychology. But there’s this other side to the professor.
Freed’s gambling problem gets him to a stage where his bookie, Hips, begins to threaten him to pay up. Unfortunately, this situation left him $44,000 in the red, which he borrows from his mother. However, instead of clearing his slate with Hips the bookie, Freed heads straight to The Strip with Billie, his girlfriend, and after a winning streak ends up going bust on basketball bets. Billie is disgusted when loan sharks start to frequent their apartment every night, which leads to frequent fights between them. His grandfather turns his request for a loan down as well.
Left with little or no options, Freed does the unthinkable. He gets one of his students who is a basketball star, to fix a game so that he can pay off his creditors. His gamble pays off but despite being warned by his bookie to stay away from a ghetto, Freed makes his way there and gets into a fight with a pimp. He ends with slashes across the face, which doesn’t seem to disturb him even though he sees blood oozing from the wounds. The climax is brilliant, get hold of the movie if you can.
The Cooler – 2003
Gambling has the potential to send many to the ‘coolers’. However, this movie is a bit different where William H. Macy is an unusual character. His streak of bad luck lands him a really ‘cool’ job at casinos. All he has to do is stand at tables where punters seem to be on a roll. His bad luck rubs off onto them and the casinos are well on their way back to restoring the house edge.
The fun really starts when Macy’s luck strikes once again and is considered a lucky charm by Vegas punters. The movie highlights gambling superstitions and could trigger your ‘laugh button’ throughout many scenes. It could probably change your concept of luck as well.
California Split – 1974
Let’s roll back to the 70s and a movie with a terrific cast. George Segal plays the main role as Bill Denny in California Split, along with Elliott Gould as Charlie Waters. Bill is a full time writer for a magazine and a casual gambler. On the other hand, Charlie is a hard core gambler with a mission to beat everyone at a poker table. Bill is steadily influenced by Charlie and as they end up spending more time together, the more he tries to copy Charlie’s ways.
From hanging out with prostitutes to gambling, the two seem inseparable. However, Bill’s life takes a turn for the worse when he gets deep into debt and the loan sharks start hounding him. This only makes the duo more determined to make more money playing high stakes poker in Reno.
Bill is on a roll with $18,000 after a winning streak at the blackjack and roulette tables, and tops it up at the craps tables. With $82,000 each in their pockets, Bill decides to call it a day but Charlie couldn’t initially come to grips with it. However, he soon realizes that Bill is serious and they decide to move on and still part as friends. Watch this film for it’s a lot more about comedy than just gambling. Incidentally, it was nominated for Writers Guild of America Best Comedy award.
The Sting – 1973
Starring two of the most handsome dudes from Hollywood, Paul Newman (Henry Gondorff) and Robert Redford (Johnny Hooker), The Sting is probably one of the best gambling movies of all times. The two play the role of confidence tricksters at the height of the Great Depression in 1936. It’s a film where charm and humor combine to keep the audience entertained throughout. Hooker comes up with an elaborate scam to avenge his friend’s murder by a racketeer named Lonnegan and ends up hiring Gondorff for the job.
The duo rustles up a team of conmen who also hate Lonnegan and are willing to go ahead with the plan. There are plenty of twists and turns in the plot that gets more complicated and dangerous for the duo. The FBI is involved and ends up with one of its members, Agent Polk, being part of the con. The movie ended up with seven Academy Awards, which is reason enough to watch it if you haven’t yet or even if you have, it’s well worth another run.
Lock, Stock and Two Smoking Barrels – 1998
This British crime comedy directed by a former Wales international footballer, Guy Ritchie, was a low budget film that grossed over $28 million. The story involves an astute card player and friends who end up losing half a million to a powerful gang lord in a game that was rigged. Desperate to pay off the debt, the group decides to plan a robbery. Their goal is to zone in on a small time gang in the next door flat that were in the process of planning to rob some drug dealers themselves and take away their loot. The gang is successful in their heist but things go awry when they try to sell the drugs to a gangster who realizes that the drugs were stolen from his own growers.
There are many more gambling related movies that we’d like to showcase but let’s leave that for another round. Nevertheless, we hope you’ve enjoyed this list. There are plenty of ways to get your hands on a copy of these films. You could always buy a copy or find them on one of the subscription film sites.