Watching movies is a gamble. You take a risk every time you buy a ticket at the theater, or queue up a movie from your couch. Will it be worth the 13 bucks? Will it be worth the two hours? There’s always a risk when it comes to picking a movie, but there are ways of limiting that risk; like, say, reading a list of the best movies in the genre.
If you like gambling movies give these bonafide classics a whirl.
California Split is the Citizen Kane of gambling movies, and Elliot Gould gives a career-best performance as Charlie Waters, the serial gambling addict who can literally bet on anything. Gould commands the screen with cocaine-fast charisma, while Robert Altman’s casual realism sucks you into every frame, casino, and horse race.
Betting has never seemed as bitterly hopeless as it does in the Safdie Brother’s intense farce about a jeweler (Adam Sandler), the mob, and Kevin Garnett. New York becomes a manic monstrosity full of bookies, sad sacks, and noise; the entire city seems to reflect Sandler’s down-on-his-luck, out-of-options plunger.
Alright, we know this isn’t really a gambling movie. But come on, it’s got Vegas, poker, and slot machines. Plus, robbing three casinos is kind of a gamble, right?
Clive Owen has been in a lot of bad movies. 43 of them, to be exact. But he does have some gems, like this 1999 cult classic about a croupier who spins roulette tables by night, writes novels by day.
Wake in Fright is one of the best gambling movies of all time, and most people don’t even know what it is. Let me break it down for you: Gary Bond plays a school teacher in Australia, blonde, tan, drenched in sweat. He winds up in a small town where there is no water–only beer–and everyone is Stepford Wives-level sexist. Madly, things get worse when he gambles away all his money. If you couldn’t tell by the title, things go from worse, to even worse, to downright frightening.
If you don’t think Maverick is a great satire, consider that it was nominated for an Academy Award in 1994. Mel Gibson sells every joke and shootout and card game, and he also reminds us how great comedy can be when the star commits to the bit.
Martin Scorsese doesn’t seem interested in gambling. He doesn’t even seem interested in casinos, which is weird since the movie is called Casino . He’s interested in people, and with two eccentric mobsters as the main characters, and two eccentric actors in the leading roles (Robert De Niro, Joe Pesci), he’s got all the firepower he needs to craft another classic, adrenaline-fueled character study.
When Phillip Baker Hall, John C. Reilly, Samuel L. Jackson, and Paul Thomas Anderson are on the table, it’s a Royal Flush. Assuming you like your casino movies with a tinge of tragedy, Anderson’s debut feature, about a veteran card player and a lonely orphan, is a riveting exploration of the men who spend their lives in Vegas.
Although Vegas Vacation is the worst Vacation movie by a long shot, it’s also got some solid gambling moments. Case in point: A hilarious scene where Chevy Chase goes to a discount casino and plays a game called “Guess a Number Between 1 and 10.” He guesses “4.” The dealer says “7.” It perfectly sums up how casinos stack the deck against unsuspecting visitors.
If you’ve ever sat down at a poker table, looked across the board, and rubbed your hands like Birdman, watching the cocky Steve McQueen lose all his cash will give you Vietnam flashbacks. Gamblers beware: this one isn’t for the faint of heart.
Dr. No has an all-time Baccarat scene. Sean Connery lays on the charm at the Craps table in Diamonds Are Forever. But if we’re going to include a Bond film (and how could we not?), it’s gotta be Casino Royale, which features a poker game in which Bond goes head to head with a terrifying villain, Le Chiffre.
Speaking of scary poker games, Lock, Stock, and Two Smoking Barrels starts with a poker game and ends with a gang war. Who knew pocket 6’s could be so fatal?
Believe it or not, The Gambler really happened. James Toback based the screenplay on his own gambling habits, which might explain why he’s been hit with so many allegations for problematic behavior. His character is cruel, lost, sexist, and addicted to betting. To channel that into a movie, however, is one gamble that pays off.
The highest-grossing film of 1988–a year that also included Die Hard, Coming to America, and Who Framed Roger Rabbit— Rain Man coasts off its feel-good charms, particularly the blackjack scene between Tom Cruise and Dustin Hoffman.
Ping-ponging from casinos to hotel rooms to long monologues with her father (Kevin Costner), Molly is a show-stopping show-runner who runs a lucrative operation that allows rich people to gamble with other rich people. Jessica Chastain is so good in the role you sometimes forget about all that drivel coming out of Arron Sorkin’s script.
Is The Cooler at all realistic? Well, William H. Macy plays a loser who is so good at losing that a casino highers him to sit at a craps table and ruin everyone else’s luck. Also, Maria Bello has sex with him. It’s dumb, gonzo fun, without an ounce of realism in its body.
After he became the laureate of loneliness in Casablanca and Treasure of the Sierra Madre, Humphrey Bogart turned on the charm in films like Sabrina and The African Queen. Sitting in-between those two periods is The Big Sleep, a charming, sleazy noir about a private eye who flirts with Lauren Bacall and caresses her gambling debts.
An homage to the Holy Grail of gambling movies, California Split, this two-hander takes all the scenes from Altman’s classic and somehow ups the ante. How? Two words: Ryan. Reynolds.
While not as good as Oceans 11, the line, “I don’t gamble, not with people’s lives” is maybe the best in the entire franchise.
Any list about gambling movies has to include one of the most famous examples ever committed to celluloid: George Roy Hill’s The Sting . This Best Picture Winner may be playing with a stacked deck–Paul Newman+Robert Redford=a full house–but it’s also playing with a cool style, boasting some of the smoothest, most entertaining scenes in genre history.
Paul Schrader makes stern, austere and existential movies about stern, austere and existential people. So why should his poker movie be any different? The Card Counter is less about cards and more about grief, trauma and faith, and it delivers those themes through the dark dazzling eyes of Oscar Isaac.
Gambling and noir go together like chicken and waffles. On their own, they’re great. But pair them together–the high stakes of poker, the seedy underworld of Los Angeles– and you got a match made in heaven.
This 1961 masterpiece has it all: pool games, trick shots, high-stakes, a too-cool-for-school Paul Newman. It’s even got a sense of melancholy, an aching feeling that pool isn’t enough for Fast Eddie (Newman); he’s got to stick it to the man. The only thing it doesn’t have? Tom Cruise.
A 25-year gap between two films in the same franchise usually means it’s a cash-grab, but Paul Newman’s return as Fast Eddie is anything but. Thanks to Martin Scorsese’s direction, plus an award-winning turn from Tom Cruise, The Color of Money is proof that not all sequels have to be scams, even when they are, in fact, about scams.
“Pay dat man his money!” No one can deliver a line quite like John Malkovich (“pay dat man his money” is now a t-shirt), and no one can play a boy genius quite like Matt Damon. Following Good Will Hunting, Damon plays the smartest guy in the room (again), this time as a professional poker player who really, really wants to win some money. Spoiler alert: dat man gets his money.
Asher Luberto is a film critic for L.A. Weekly, The Playlist, The Progressive and The Village Voice.
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