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I’ve spent a surprisingly large percentage of my hours living watching movies in a theater or in the comfort of my own home. I love the movies, and I love gambling.
Luckily, I’ve been able to find plenty of great movies about gambling and gamblers.
It’s easy to find lists of films about the life of a gambler, but none of them are as good as the one I’ve put together. I promise.
Spoiler warning: I go into considerable detail about the plot points of several of these films. I you want to see these movies unspoiled, read no further.
Here are the 10 absolute best movies about gambling and gamblers:
1- The Hustler
This is my favorite gambling movie on the list, and it was made in 1961. Robert Rossen directs and co-writes along with Sidney Carroll. The Hustler is an adaptation of the novel of the same name by Walter Tevis.
The movie tells the story of a minor pool hustler named Eddie Felson (Paul Newman). His goal is to become a professional pool player and he pits his skills against the greatest pool player in the country, Minnesota Fats (Jackie Gleason).
Felson loses, and he soon becomes associated with Bert Gordon (George C. Scott), who becomes his new manager. Gordon, by the way, is a high-stakes poker player.
The love interest (Sarah) is played by Piper Laurie.
The Hustler isn’t a big secret, either—it was a critical success at the time, and its estimation has only grown in the decades since.
The Hustler only won 2 Academy Awards, although it was nominated for 9. It won for Best Art Direction-Set Direction, Black-and-White, and Best Cinematography, Black-and-White.
The Hustler was also nominated for several Golden Globe Awards: Best Actor, Best Supporting Actor, and Best New Star of the Year.
You should see The Hustler, and you should also see its sequel, The Color of Money.
2- Hard Eight
I tend to prefer older movies, but Hard Eight is such a great film that I couldn’t imagine not including it on this list.
Paul Thomas Anderson directs, and Philip Baker Hall and John C. Reilly star. Gwyneth Paltrow and Samuel Jackson have fine supporting roles, too.
An elderly gambler, Sydney (Philip Baker Hall) takes John (John C. Reilly) under his wing after finding him sitting outside a diner lamenting the fact that he can’t come up with enough money to pay for his mom’s funeral.
He takes him to Vegas and teaches him how to make enough money gambling to live.
A couple years later, John has established himself in Vegas and has a friend, Jimmy (Samuel Jackson) and a girlfriend, Clementine (Gwyneth Paltrow).
But Clementine isn’t just a cocktail waitress; she’s also a prostitute. Eventually, she and John get into a hostage situation that Sydney has to help clean up.
Sydney eventually also has an altercation with Jimmy, who recognizes him as a gangster from the old days.
Hard Eight takes its name from the bet that Sydney always makes at the craps table, which, as you know if you read my column, has lousy odds. Phillip Seymour Hoffman has a great cameo at the craps table, in fact.
This was P.T. Anderson’s first film, and it’s well worth watching. Everything about Hard Eight is top notch—the screenwriting, the directing, and the acting are all superb.
3- The Gambler
This 1974 film was recently remade as a Mark Wahlberg vehicle, and the remake seems to have gotten good reviews. I haven’t seen it, but I have seen the original, and I have no trouble recommending it.
James Toback directs and Karel Reisz directs. James Caan, Paul Sorvino, and Lauren Hutton star.
Axel Freed (James Caan) is a gambling addict who also teaches English and writes books. In spite of his gambling addiction, he’s well thought of by his friends, family, and students.
He’s also thousands of dollars in debt to his bookie. He borrows $44,000 from his mom to pay the debt, but he takes the money to Vegas and loses it all betting on basketball.
He then asks his grandfather for help, but his grandfather has the good sense to turn him down.
He finally bribes one of his students to shave some points in a game. This gets him off the hook with the bookie, but Axel wanders into the ghetto and intentionally gets into a fight with a pimp after refusing to pay a prostitute.
James Caan was addicted to cocaine at the time of filming, so he had something to draw from when portraying a man who’s addicted to gambling.
Also, the film can be seen as a loose adaptation of Dostoyevsky’s The Gambler.
It’s a fine film and a good example of what cinema had to offer in the 1970s.
4- House of Games
I’m a huge fan of David Mamet, so 1987’s House of Games was a no-brainer for this list of the best gambling films. Mamet also wrote the screenplay, and the film stars Lindsay Crouse, Joe Mantegna, Ricky Jay, and J.T. Walsh.
Margaret Ford (Lindsay Crouse), a psychiatrist and author, is bored, but one of her patients owes money to a crook, Mike (Joe Mantegna). She goes to Mike’s pool hall to discuss her patient.
Mike agrees to forgive her patient’s debt under one condition:
She has to identify a poker player’s tell during a poker game. She notices that George always toys with his ring when bluffing, and Mike uses this information to call a bluff. George wins anyway, and guns get drawn. Margaret offers to pay George off but soon realizes the entire set-up was a con.
She comes back the next night and asks Mike to teach her about cons so she can write a book on the subject. He agrees, and they soon become lovers. She also starts accompanying Mike on his cons, but soon they run afoul of the police.
More cons and double-crosses ensue, and Margaret eventually kills Mike over a huge con job he tried to put over on him.
You should find the special edition of House of Games that Criterion released and watch, then re-watch, this movie. It’s fantastic on every level.
5- Indecent Proposal
I used to drink a lot, and one night I had too much to drink and offered a woman some money that I probably shouldn’t have. My drinking buddy told me that they should make a movie out of this called Sordid Proposition. He’s a clever guy, that drinking buddy of mine.
But I digress.
Indecent Proposal is loosely based on a novel by Jack Engelhard. The premise is that a young married couple accepts a billionaire’s offer of $1 million to spend the night with the young woman. Adrian Lyne directs, and Robert Redford, Demi Moore, and Woody Harrelson star.
David (Woody Harrelson) and Diana (Demi Moore) go to Vegas to try to win enough money to save a piece of real estate. They have a big winning streak, but they eventually lose all their money.
But John Gage (Robert Redford), a billionaire, offers them $1 million to spend the night with Diana. They accept, and Gage flies Diana to his yacht, where they consummate the deal.
David can’t handle his feelings and the tension causes the young couple to separate. Gage begins courting Diana.
David eventually pulls his act together, and the couple divorce.
But Diana and John separate, too, mostly because John realizes she’ll never love him the way she loves David.
David and Diana seem to reconcile at the end of the film.
It’s well worth seeing, but skip the novel. It’s almost unreadable.
6- The Killing of a Chinese Bookie
You might have gathered already that I’m something of a film snob. And like most film snobs, I’m a huge fan of John Cassavetes, who wrote and directed this gritty noir from 1976. Ben Gazzara stars as Cosmo Vittelli, the owner of an unusual strip club in California.
This is also a movie about a gambling debt. Vittelli owes money to a loan shark who he pays off. Eventually, though, the loan shark entices Vittelli to gamble at his mobster friend’s underground casino.
This is one of my favorite scenes in the film, as Vittelli does it up right, bringing along 3 of his favorite strippers on his gambling excursion.
He loses over $20,000 playing poker that night, so he’s now again in debt. The mobsters explain to him that since he can’t pay his debt, he needs to work it off by performing a hit on a small-time Chinese bookie.
The mobsters are lying about the bookie, though—he’s not small-time at all. He’s actually the head of the Chinese mob. Surprisingly, Vittelli pulls off the hit.
The mob didn’t even expect him to succeed, even though he suffered a major gunshot wound in the process. The film ends with uncertainty, as we’re not sure if Vittelli survives his subsequent encounters with the Italian mobsters who double-crossed him.
The Killing of a Chinese Bookie is a cult favorite, and you should see it.
7- Rounders
It’s hard to imagine that Rounders is now 20 years old, but the high stakes poker movie has withstood the passage of time well. John Dahl directs, Matt Damon and Edward Norton star.
Rounders came out shortly before the poker boom, and it became a cult favorite after that.
Mike McDermott (Matt Damon) is a law student and poker player who risks $30,000 in an underground cardroom operated by Teddy KGB (John Malkovich). He loses all of it and decides to quit poker.
But then Worm (Edward Norton) gets out of prison. Worm owes money, and Mike helps him find poker games. Eventually he sits in and plays in one of the games with him, and he allows Worm to play on his own credit at one of the rooms.
Worm wins but leaves the cardroom with debt in Mike’s account. And Worm still owes money to a pimp who’s associated with Teddy KGB. They beat Worm up for owing them money, and Mike’s girlfriend dumps him.
Worm then goes on a losing streak, still on Mike’s credit. They try to negotiate some extra time from the pimp, but Worm is too arrogant. The pimp gives him 5 days to pay off the debt, and Mike agrees to play poker to pay off Worm’s debt and save his life.
He wins $7200 in 3 days, but he still needs another $7800 to clear up Worm’s debt. At a private game full of state troopers, Worm shows up and starts cheating to help Mike win the rest of the money. They get caught, and the state troopers beat them both up and take all their money.
Mike asks for an extension on the debt, but the pimp tells him to negotiate with Teddy KGB. He winds up borrowing $10,000 from his law professor and uses the money to challenge Teddy KGB to a heads-up holdem game, winner take all.
Mike eventually wins enough money to pay off all his debts and go to Vegas to play in the World Series of Poker.
But if not, you should see it immediately. It’s too good to miss.
8- The Cincinnati Kid
Like many of the films on my list, The Cincinnati Kid is an older movie—it was made in 1965. Eric “The Kid” Stoner (Steve McQueen) is a poker player during the Great Depression who wants to be the best player in the world.
To establish himself as the best, he eventually must play and defeat Lancey “The Man” Howard (Edward G. Robinson).
Reviews for The Cincinnati Kid were mixed, but it’s become a major classic among gambling movies.
9- The Cooler
Wayne Kramer directs from a screenplay he co-writes with Frank Hannah.
The title refers to an unlucky employee at the casino who hangs around gambling tables to create bad luck for a player who’s been winning.
Bernie Lootz (William H. Macy) is the titular cooler in this film. He’s a loser living in a motel in Las Vegas, and he owes a fortune to Shelly Kaplow (Alec Baldwin), who broke his knee years ago.
Lootz has since given up gambling, and he now works as a cooler at Shelly’s casino, The Shangri-La. Instead of getting paid, his wages go toward re-paying his debt to Shelly.
Lootz plans to leave Vegas when his debt is settled, but his luck changes when Natalie (Maria Bello) falls for him. Unbeknownst to Lootz, Sheely paid Natalie to seduce Lootz so he won’t leave town.
But Natalie turns out to have a heart of gold, and she and Lootz really do fall in love.
Things get more complicated. Shelly conflicts with Larry Sokolov (Ron Livingston), one of the young, new investors in the Shangri-La, who wants to modernize the casino.
The main reasons to watch this one are the stellar performances from all 3 of the leads, but especially Alec Baldwin as Shelly.
10- Vegas Vacation
Okay, did I say that The Hustler is my favorite gambling movie?
I take it back.
Vegas Vacation is my favorite gambling movie.
Stephen Kessler directs this 4th installment in the Vacation series. Elisa Bell writes. The usual cast for Vacation movies stars, including Chevy Chase, Beverly D’Angelo, and Randy Quaid.
Ethan Embry and Marisol Nichols appear as Rusty and Audrey, the 2 kids, who are played by different actors in all the Vacation movies.
Clark Griswold (Chevy Chase) invents a food preservative and gets a huge bonus check, which he uses to take his family on a vacation to Las Vegas.
Hijinks ensue. Some of the funniest scenes belong to Cousin Eddie (Randy Quaid), who lives in the desert near Vegas with his family. The Griswolds go see Siegried & Roy, Hoover Dam, and Wayne Newton.
The family separates, and each of them has his or her own adventures in Vegas. Clark loses a fortune playing blackjack, Rusty becomes a high roller with a fake ID, and Audrey parties with her cousin. And Ellen (Beverly D’Angelo) is courted by Wayne Newton.
Cousin Eddie eventually has to bail Clark out with money he has buried in a jar in the desert. Clark loses all Eddie’s money, too, and hits rock bottom. He realizes that his family is what matters, not gambling.
The family bet their last $2 on a game of keno. They lose, but the old man sitting with them dies during the game. Clark gets his winning ticket.
The family then pays Eddie back and drive home in 4 brand-new sports cards that Rusty won while masquerading as a high rolling gambler.
Critics seem to hate this movie, but they’re wrong. If you love Las Vegas and gambling, Vegas Vacation might be the best gambling movie ever made.
Conclusion
Those are my 10 favorite movies about gambling and gamblers.
What movies make your list of favorites?
