Home Entertainment Top 20 Gambling Movies of All Time

Top 20 Gambling Movies of All Time

by Scott Kacsmar
0 comment
Casino 1995 - IMDb

Gambling has always been ripe for movie-making because it is an activity that encompasses the most visceral feelings in the human condition from hope, bliss and joy to sadness, addiction, greed, and misery.  From intense, high-stakes, poker scenes to the inner workings of casinos and the shady business of loan sharks and mobsters, gambling movies have touched on many topics over the decades. So, if you are looking for inspiration before playing at one of our recommended offshore sportsbooks, we are looking at the top 20 gambling movies of all time. Not included in the list are films that are only gambling adjacent such as Casino Royale, which is still at its heart a James Bond spy film.

20 The Card Counter (2021)  

A film written and directed by Paul Schrader (Taxi Driver, Raging Bull, First Reformed) and starring Oscar Isaac probably should have been better than the final product turned out to be. But this is still an engaging watch with great performances by Isaac and Willem Dafoe.  Isaac plays William Tell, a gambler with card-counting skills who also has a troubled past with time spent in a military prison. He meets a young man (Cirk, played by Tye Sheridan) who has a personal link to the same military prison, and the plot soon turns to revenge with Dafoe’s character the target. It is a dark but hypnotic take on a gambler’s life. 

19 Vegas Vacation (1997) 

Sure, it may be the worst of the Griswold family movies in the National Lampoons series, but it’s still fun to watch for nostalgia. You get to see Clark (Chevy Chase) act jealous of Wayne Newton’s pursuit of his wife Ellen, Rusty can’t stop winning cars at the casino, Audrey has never been played by a more beautiful actress (Marisol Nichols), and Wallace Shawn (as Marty) is perfect as the dealer who keeps beating Clark at every casino game.  This movie also taught many of us what keno is as it plays an integral role in the final act. Plus, you can never get enough scenes of Randy Quaid as Cousin Eddie.

18 The Killing of a Chinese Bookie (1976) 

John Cassavetes was a master filmmaker, and this collaboration with Ben Gazzara saw them both at the height of their powers in the 1970s. This is a gritty film with Gazzara playing Cosmo, the owner of a strip club in Los Angeles. Cosmo is finally about to pay off a 7-year gambling debt to a loan shark before he parties hard and racks up another $23,000 in poker debt. Old habits die hard.  To wipe this debt out, Cosmo is offered a job from a gangster to kill a Chinese bookie as the title of the film suggests, but the job is anything but what it sounds like in this entertaining cult classic from the 70s.

17 The Color of Money (1986) 

This won’t be the last film directed by Martin Scorsese on our list. Some feel this sequel to The Hustler was better than the original, though I must disagree there. But we do see Paul Newman reprise his role as “Fast Eddie” Felson, which led to the only Best Actor Oscar win of his legendary career.  In this sequel, Felson has moved on from playing pool to selling liquor, but he soon meets up with a cocky young pool player named Vincent, played by rising star Tom Cruise. Eddie finds himself teaching Vincent and his girlfriend how to hustle pool players, and the trio eventually land in Atlantic City for a pool tournament.  

16 Ocean’s Eleven (2001) 

It is rare for a remake to surpass the original, but Ocean’s Eleven did that from director Steven Soderbergh. Based on the 1960 film with the Rat Pack, there have since been several sequels, but this first one from 2001 remains the best and one of the better heist movies in recent decades.  In an all-star cast led by George Clooney and Brad Pitt, we see Danny Ocean (Clooney) plot an elaborate heist of a casino owned by Terry Benedict (Andy Garcia). The recruitment of the 11 men for the job and the planning that goes into it are among the highlights of the film, and none of the sequels ever surpass the quality of those scenes here.  Julia Roberts, Elliott Gould, Don Cheadle, Carl Reiner, Bernie Mac, and Matt Damon (among others) round out a great cast. 

15 House of Games (1987) 

Legendary writer David Mamet (Glengarry Glen Ross, The Untouchables) made his directorial debut with one of the best con artist movies ever made. Margaret Ford (played by Mamet’s ex-wife Lindsay Crouse) is a psychiatrist who tries to help a troubled patient, Billy, who owes gambling debts to a bad man named Mike (Joe Mantegna).  She is taken to the House of Games, which is a pool hall with a poker room in the back. Mike gives her a task to pick up on a player’s tell during the poker game, and if she does, he’ll forgive Billy’s debts. She agrees, and without spoiling anything, it leads to a series of cons with Margaret falling deep into this new, dangerous lifestyle.  

14 Molly’s Game (2017) 

Based on a true story, Molly’s Game is Aaron Sorkin’s directorial debut about Molly Bloom, who ran a high-stakes poker game for elites in Los Angeles. Michael Cera plays Player X, who is reportedly a composite character based on real-life celebrities Leonardo DiCaprio, Tobey Maguire, and Ben Affleck.  Molly soon becomes involved in a dangerous game with Player X, Italian and Russian mafia members, and the FBI, leading to a trial. Jessica Chastain does a fantastic job as Molly in one of her best career roles in arguably the best poker movie since Rounders. 

13 Hard Eight (1996) 

Before he became a household name, Paul Thomas Anderson’s directorial debut was a hidden gem in the mid-1990s. An expansion on his short film Coffee & Cigarettes (1993), Hard Eight follows Sydney Brown, an experienced gambler played by the great Philip Baker Hall. He befriends a homeless man, John (John C. Reilly), who needs $6,000 for his mother’s funeral.  They travel to Vegas to win John the money. Two years later, John acts as a protégé to Sydney, and they meet a waitress/prostitute played by Gwyneth Paltrow in one of her early roles. Samuel L. Jackson also has a big role, and the film features Philip Seymour Hoffman, another favorite collaborator of PTA’s, in a small role as a craps player. If you’re a fan of Anderson’s other films and have never seen his first, you owe it to yourself to check this one out. 

12 Croupier (1998) 

Before he was well known to audiences, Clive Owen shined in this 1998 film where he plays a writer who takes on a job as croupier (dealer) at a casino. Soon, the casino lifestyle engulfs him, and his novel work suffers for it. But Owen carries the movie with his inner dialogue, which was a perfect fit for a movie about a struggling writer as it gives the story a classic noir feel.  

11 The Gambler (1974) 

Make sure to watch the original with a standout performance from James Caan and not the 2014 remake with Mark Wahlberg. This was a great blueprint for the 2019 film Uncut Gems as we follow a college professor, played by Caan, who has a bad gambling problem that leads him to hot water with his bookie and the mob.  We see the highs and lows of Caan’s gambling as this one has everything from a fight with a pimp to a point shaving subplot to a bad beat in a game involving the Lakers. The final shot of Caan will be seared in your memory as we see how much gambling takes ahold of him.

10 Mississippi Grind (2015) 

You might not think an Australian (Ben Mendelsohn) and Canadian actor (Ryan Reynolds) would be a good fit for something set in Mississippi, but the duo makes it work with great chemistry in one of the 21st century’s best gambling films.  Mendelsohn plays the experienced gambler who has been down on luck recently with his personal and gambling life, and Reynolds is the younger, enthusiastic learner. They mingle with muggers, loan sharks, and a prostitute during their road trip to find action at card games and other gambles before ultimately winding up in a Mississippi casino where they risk it all. 

9 Atlantic City (1980) 

While many gambling movies focus on the shenanigans in Las Vegas, this classic from director Louis Malle (My Dinner with Andre, Au revoir les enfants) uses its title city as the setting. Lou, played by Burt Lancaster in his last great role, is an aging gangster who runs a numbers game.  Sally (Susan Sarandon) is a waitress working at an oyster bar in an Atlantic City casino, and she dreams of being a blackjack dealer. But when her ex-husband shows up with intent to sell a huge bag of cocaine, she winds up crossing paths with Lou. Suddenly, love, murder, and danger follow them. 

8 Rounders (1998) 

Fresh off his star turn in Good Will Hunting, Matt Damon starred with Ed Norton in arguably the best movie ever made about high-stakes poker. Damon plays Mike McDermott, a NYC law student and great poker player who dreams of playing in the World Series of Poker. But he opts for an underground poker game run by Russian mobster Teddy “KGB” (played wonderfully by John Malkovich) where he loses his entire $30,000 in one hand.  Vowing to quit poker for good, Mike gets sucked back in after his friend Worm (Norton) needs to pay a debt. The final confrontation at the poker table between Mike and KGB puts this one over the top as a gambling classic. 

7 The Hustler (1961) 

Maybe Tom Cruise just doesn’t do it for me, but the reason I like The Hustler over its sequel (The Color of Money) is that we get to see Paul Newman in his prime as young pool hustler Eddie Felson, and he has a target in mind this time.  Minnesota Fats, played to a tee by Jackie Gleason, takes Eddie for a ride in a marathon pool session before the cocky Felson finally loses all his money. Needing to hustle to get the money needed to challenge Fats again, we watch Felson do whatever is necessary to get back on top. A classic that has aged well.

6 Lock, Stock and Two Smoking Barrels (1998) 

Guy Ritchie’s full-length directorial debut immediately put his name on the map, and it introduced actor Jason Statham to the world. It barely cost over $1 million to make but still made over $28 million at the box office.  This black comedy gem sees a group of friends pool their money so their expert friend can enter a high-stakes game of three-card brag, an old British card game. After finding out the game was rigged, the friends owe a gang 500,000 pounds. They plan a heist to get money from a small gang in the next flat, but things do not go as well as hoped for in this vulgar, entertaining comedy. 

5 The Sting (1973) 

An instant classic upon release, The Sting remains high in replay value with Paul Newman and Robert Redford offering great performances as grifters who con a mob boss (Robert Shaw) through a series of rigged card games and horse races.  The Sting won 7 Oscars, including Best Picture, Best Director, and Best Original Screenplay. Who knew a revenge story set in the 1930s could be this fun to watch? They don’t make them like this anymore in Hollywood.

4 Bay of Angels (1963)

Only the second film from famed French director Jacques Demy, Bay of Angels is hands down the best movie ever made about roulette. Jean gets a taste of gambling at a casino against his father’s best wishes, then things really heat up when he meets Jackie, a tempting blonde played by screen legend Jeanne Moreau.  For Jackie, gambling is about the thrill and not the money she wins. Roulette becomes the game of choice for Jean and Jackie, but will their addiction destroy their new relationship, or is that the only thing keeping them together in the first place?

3 California Split (1974)

“It don’t mean a f***ing thing, does it?” The ending to California Split by legendary director Robert Altman is one of the realest you’ll ever see in a gambling movie. Elliot Gould was the coolest of cool in the 1970s, and we see that dynamic play out with his more strait-laced co-star George Segal.  But after a big win, Gould’s character Charlie Waters, the carefree gambler who lives with two prostitutes and is always seeking the next big score, has a moment of reflection in the final scene that’ll break your heart.  And if you’re anything like Charlie, you’ll be onto your next bet before the credits finish rolling. No moment in any other gambling movie captures the thrill of the hunt and the melancholy of the moment passing quite like California Split. The ride to the ending is also very fun as this is Altman and Gould at the peak of their careers.

2 Uncut Gems (2019) 

The Citizen Kane of sports betting movies, Uncut Gems is the Safdie brothers’ chaotic look into the life of New York City jeweler and gambling addict Howard Ratner, played by Adam Sandler in arguably the best performance of his career.  Ratner must retrieve a rare gem to pay off his gambling debts, and we see him in the final act place one of the wildest parlays imaginable involving the Boston Celtics winning the game’s opening tip, Kevin Garnett (who stars as himself) putting up big numbers, and the Celtics winning the game.  The frenetic pace and general loudness of the film may be off-putting to some, but no selection on our list captures the glory, despair, and sometimes tragedy of sports wagering better than this one did.

1 Casino (1995)

Martin Scorsese’s epic masterpiece is still highly rewatchable to this day as it is essentially Goodfellas set in Las Vegas with Joe Pesci playing another hothead named Nicky Santoro.  But this is Robert De Niro’s film as leading man and narrator Sam “Ace” Rothstein, a brilliant sports handicapper who is sent by his Chicago Mafia associates to set up shop at the Tangiers Casino in Las Vegas. The events unfold in the 1970s and 1980s with Ace and Nicky finding themselves in deep water with the Mafia, pressure from the FBI, and anxiety from Ace’s troubled wife Ginger, played by Sharon Stone.   There may be better movies about the art of gambling itself, but if you want the history of the Mafia’s link to Las Vegas seen through the eyes of an incredible cast and masterful direction, then there is no better choice than Casino.
author avatar
Scott Kacsmar
NFL football picks are Scott Kacsmar's expertise, serving as his main focus. He has contributed to various sports websites and blogs, such as NBC Sports, ESPN Insider, FiveThirtyEight, and, JoeWager. Originating from Pittsburgh, Scott maintains a love-hate connection with the Pirates.

You may also like

JoeWager is your leading source for trending topics relevant to offshore gamblers, including betting resources, sports & casino guides, entertainment topics, politics and more.

Editors' Picks

Latest Articles

Copyright 2023 – All Right Reserved.

This website uses cookies to improve your experience. We'll assume you're ok with this, but you can opt-out if you wish. Accept Read More