The Gambler, Kenny Rogers, said it himself in his hit song aptly titled The Gambler (that also spawned a series of TV movies), that “You got to know when to hold ‘em, know when to fold ‘em,” and blah, blah, blah. Well, I’ve decided to hold ‘em as I present my list for the greatest gambling movies. After all, there’s nothing like a little risk to get the blood flowing. Now, the problem with this list is that there are actually a ton of films about the subject and I haven’t been able to view them all. Additionally, another bummer is that many of the most worthwhile gambling movies unfortunately are currently not available on video. (Is this a government conspiracy?) However, I’m not going to let these little obstacles deter me (Maybe I don’t know when to fold ‘em.) from paying tribute to one of America’s favorite pastimes… that is, losing one’s hard-earned money to big business in some of the most ridiculous ways possible.
Now, not all films featuring games of chance are solely about gambling. That would probably be tough to pull off and most likely relatively uninteresting. Such films featuring a turn of the card, roll of the dice, etc. are usually used to fuel a narrative concerning a bigger human drama, but I did my best to whittle this list down to films that feature gambling as a central plot device as much as possible. Therefore, I’m going to give an honorable mention to titles such as Hard Eight and Two For The Money, because while they feature and deal with gambling, the activity isn’t quite as focal as some other solid efforts that handle the topic. I’ll also throw in 21 and California Split. Sadly, I haven’t seen these two, but they’re on my list, and I mention them only because I’m convinced that they have to be enjoyable films. So, without further delay, here are the greatest gambling releases of all time, in no particular order.
A Big Hand For The Little Lady (1966): A totally fun and brilliantly paced little movie has Joanne Woodward and her compulsive gambler of a husband Henry Fonda stumbling into the biggest poker game in town, held once a year for the richest men in the county. Seeing this as a sign for him to make a killing, Fonda risks his life savings to get into the game, much to the chagrin of Woodward. However, when the excitement of the game becomes too much for Fonda, the innocent and supposedly ignorant Woodward must step in to play for him. Funny, with great performances from an incredible supporting cast including Jason Robards, Kevin McCarthy and Burgess Meredith, the film perfectly embodies the spirit and rush of poker.
The Sting (1973): OK, for some this title may be an obvious choice, and for others it may be an odd one since the movie is more about the art of the con. However, I would probably have to turn in my membership card as a gambler, a film buff, and perhaps even a man if I didn’t include it on this list. The title is an Academy Award winner, so no one needs me to exclaim how awesome it is. However, there’s plenty of gambling in the film (including characters gambling with their lives), the poker scene between Paul Newman and Robert Shaw is amazing, and the main aspect of the title deals with taking down Shaw through betting on the horse races, so it seems fitting that George Roy Hill’s masterpiece gets a rightful place on the list.
The Gambler (1974): Perhaps the quintessential gambling film, it features James Caan as an otherwise intelligent literary professor with a gambling addiction who gets in way over his head. It’s a brilliant character study, and Caan is intense and riveting as man who feels he’s always on the edge of his next big score but is incapable of recognizing his real problems. He eventually goes in debt to the mob, and to get even he of course tries to gamble his way out. There are scenes such as when Caan takes a very ill-advised hit on a hand of blackjack while he’s on a rush, and moments of complete discomfort while he listens to a basketball game he has bet on while he’s in the tub, that are undeniably impactful.
The Hustler (1961)/The Cincinnati Kid (1965): Yeah, it’s probably cheating to include two films in one slot, but bear with me. While it would have been controversial, I almost left The Cincinnati Kid off my list, because as I’ve made known in a previous piece, I feel the Depression Era poker effort with Steve McQueen is a touch overrated and flawed. However, there are great performances in it (especially McQueen and Edward G. Robinson) and the poker scenes are entertaining. I decided to slip it alongside The Hustler since the two movies are very similar in tone, scope and subject matter, with the obvious exception of The Hustler utilizing billiards to tell its story instead of cards, and the two are often measured against each other, anyway. Additionally, I feel The Hustler is a far superior film as far as gambling is concerned. The rivalry between Fast Eddie Felson (Paul Newman) and Minnesota Fats (Jackie Gleason) is one of the best in film history.
Let It Ride (1989): This underrated farce features Richard Dreyfuss as man who has spent much of his life losing money at the racetrack. However, after promising wife Teri Garr that he’ll quit, he gets a hot tip on a horse and bets everything he has (a whopping $50) on one “final” hurrah. Miraculously, he wins, but instead of quitting Dreyfuss decides to “let it ride” and experiences an incredible wave of good luck. It’s so good in fact, that one can’t help but wonder when it will run out. Not only is the film uproariously hilarious, but for me it mirrors the choices we all make with our lives. There are some critics who revile this movie and I don’t understand why, so I’ll take this opportunity to call them all a bunch of jaded hacks.
Croupier (1998): Quoting Ernest Hemingway from A Farewell to Arms, lead character Clive Owen states, “The world breaks everyone and afterward many are strong in the broken places.” Thus begins this tough tale, as aspiring author Owen takes a job as a dealer at a London casino in order to acquire material for his novel. He becomes coldly detached and even creates an alter ego for himself, with the intention of using this alternate persona as the protagonist of his book. However, as Owen becomes more and more immersed in the seedy world of gambling, it becomes increasingly tough to tell where the real Owen begins and his fictional character ends. Matters get really dire when he gets involved in a plot to rob the casino. The film is unique, surprisingly tense and stylistic, and it’s incredibly interesting to witness a story from the casino dealer’s point of view.
Rounders (1998): This is perhaps the grand daddy of them all. Most likely the greatest film ever made about the game of poker, it stars Matt Damon as a pro caliber poker player who has given up the game to concentrate on his law degree (and keep his girlfriend happy, due to getting in over his head). However, when his best friend (Edward Norton) gets released from prison looking to make it big, Damon gets sucked back into the game when Norton goes in debt to loan sharks. This leads to a showdown between Damon and head honcho Teddy KGB (essayed brilliantly by John Malkovich, with the exception of maybe the Russian accent). The movie delves pretty deep into various poker nuances such as tells (even though the Oreo cookie tell is perhaps a bit silly), strategy, etc. and features the Cadillac of poker, no limit Texas hold ‘em. Any fan of poker will say that any game that doesn’t feature exposed cards isn’t a real game, and many gambling films unfortunately don’t feature this kind of game. Anyway, the whole effort is entirely engaging, with great supporting turns from Famke Janssen and Martin Landau, and even features two-time World Series of Poker Main Event Champion Johnny Chan in a cameo appearance.
The Cooler (2003): This one may not focus on gambling quite as much as the others, but I find the idea fascinating that casinos would employ a gloomy, downtrodden man to bring bad luck to gamblers on hot streaks. That’s the basic gist of this gem, as William H. Macy plays the said “cooler,” who quickly puts an end to someone’s good luck merely by standing next to the person. How does he do this? Simply by being himself. Macy is a born loser. However, this all begins to change when he enters into a loving relationship with waitress Maria Bello. All of a sudden, “lady luck” is on his side, and the fact that he’s feeling good about himself is having dire consequences for the casino, since now everyone who comes into contact with him is winning! This is all much to the dismay of Macy’s boss, Alec Baldwin, who has a sordid history with Macy. Now, Baldwin must find a way to get his cooler back under control. The film, for its premise, is so well done, with a great atmosphere and Las Vegas feel to it, and all performances are sublime, especially Baldwin’s turn, which garnered him an Oscar nomination.
Owning Mahowny (2003): This character study, based on Gary Stephen Ross’ factual book Stung: The Incredible Obsession of Brian Molony, is a superb example of gambling gone wrong in real life. Philip Seymour Hoffman is awesome as “Dan Mahowny,” a bank executive with an insidious gambling addiction. His overwhelming habits lead him to “borrow” more than $10 million from his bank, resulting in one of the biggest embezzlement scams in Canadian history. What’s most interesting is that for the otherwise smart, likable and mild-mannered Mahowny, it’s never really about the money. It’s much more about the process of gambling, the one thing that gives the Mahowny character pleasure in life, even though he knows it will lead to his downfall. All the performances are phenomenal from top to bottom, including turns from Minnie Driver and John Hurt.
Even Money (2006): I call this one the Requiem For A Dream of gambling movies, even though this film isn’t quite as compelling. “Everybody’s chasing something,” remarks the film’s narrator (Kelsey Grammer), “but what they’re really looking for is more life. However, some people may go looking for more and come away with less.” It’s pretty heady stuff, and the film pretty deftly illustrates the dangers and consequences of gambling addiction, whether it’s the slots, sports betting, or even gambling with others’ lives. Led by an ensemble, all-star cast that includes Kim Basinger, Ray Liotta, Forest Whitaker, Tim Roth, Danny DeVito and Carla Gugino, they do a fantastic job illustrating just how ugly and dire the world of gambling can get.