Calculating the Odds: Movies About Betting (Infographic)

Movies about betting have always been popular among cinephiles, and various Hollywood releases prove this trend. But why do people love to watch these movies? 

First of all, there’s usually an excellent and witty script that introduces us to unforgettable characters and luxurious locations. And secondly, let’s not forget the thrill and suspense we as an audience experience while following the protagonists’ risky moves. 

Now, get your popcorn, and enjoy some of the funniest, craziest, and the most spellbinding movies about Lady Luck.

Best Movies About Betting to Put on Your Watchlist

We compiled a list of some of the greatest movies of their decades that talk about gambling, addiction, and sports betting. In case you’re more interested in sports-related movies, you should check out our dedicated top sports movies rank list.

Best Movies of the 1980s

1. The Color of Money (1986) — Best sports drama about pool hustling

• Director: Martin Scorsese
• Box office earning – $52,293,982 million
• Main cast: Paul Newman, Tom Cruise, Mary Elizabeth Mastrantonio

Martin Scorsese took a chance with the adaptation of a novel by Walter Tevis, called The Color of Money, to create a $10 million movie of the same name. The film was an instant hit, earning more than five times its initial budget at the box office—$52 million.

This interesting gambling movie about pool hustling is also a sequel (i.e., continuation) to The Hustler (1961). The story begins 25 years after the plot of the Hustler, following the story of Edward “Fast Eddie” Felson (Paul Newman). 

Eddie is a former pool hustler who, after meeting a talented pool player, Vincent (Tom Cruise), decides to make him his protégé. What starts with a partnership in scamming people ends in an exciting duel. 

2. Eight Men Out (1988) — True story gambling movie about the biggest baseball scandal

• Director: John Sayles
• Box office earning – $5,680,515 million
• Main cast: John Cusack, Clifton James, Jace Alexander

Filmed and directed by John Sayles, Eight Men Out is based on a true story, following one of the biggest gambling scandals in baseball’s history. 

The story was set in 1919. It follows the famous baseball club, the Chicago White Sox, and their decision to throw the World Series against the Cincinnati Reds for money. 

This is one of the most thrilling historical movies about sports betting filmed on a small budget of $6,6 million. Despite the modest box office earning (only $5,6 million), Eight Men Out became one of the classics among cinephiles and baseball fans.

3. Let it Ride (1989) — Comedy movie about gambling on horses

• Director: Joe Pytka
• Box office earning – $4,973,285 million
• Main cast: Richard Dreyfuss, Teri Garr, David Johansen 

In 1989, Joe Pytka made his feature directorial debut, Let it Ride, with an $18 million budget and an idea to create one of the funniest movies about gambling on horses. The odds weren’t in his favor since the film earned only $4.9 million at the box office.

That said, Let it Ride is still one of the fan’s favorites due to its comical plot and a fantastic performance by Richard Dreyfuss.   

The plot of the movie Let it Ride revolves around two friends and taxi drivers, Jay Trotter (portrayed by Richard Dreyfuss) and his friend Looney (David Johansen). When the duo records one of their client’s horse racing tips, the game is on. 

Best Bet Movies of the 1990s

4. Diggstown (1992) — A hilarious comedy about the uneven odds of gambling

• Director: Michael Ritchie 
• Box office earning – $4,836,637 
• Main cast: James Woods, Louis Gossett Jr., Bruce Dern 

Diggstown is not your typical boxing movie since it injects a dose of humor into this usually serious genre. The plot follows Gabriel (James Woods), a con man who has just been released from prison. 

Without a minute to waste, he decides he’s going to do his next con in the city called Diggstown, where everything revolves around boxing.

What makes this one of the best movies about gambling? The odds. In order to win $100,000, Gabriel needs to bet on the boxing matches. But there’s a twist. Can his guy ‘Honey’ Roy Palmer (Louis Gossett Jr.) win the fight against the ten best fighters of Diggstown?

5. White Men Can’t Jump (1992) — The most famous sports comedy-drama about basketball betting

• Director: Ron Shelton
• Box office earning – $90,753,806  
• Main cast: Wesley Snipes, Woody Harrelson, Rosie Perez

White Men Can’t Jump started with a budget of $31 million and ended up with a staggering $90 million earnings at the box office, domestic and international combined. Not a bad haul for a comedy movie.

Like with other best gambling movies, the story revolves around a hustle. Billy Hoyle (Woody Harrelson) is a basketball player who earns money by hustling streetball players pretending that he can’t play because he’s white. 

When he meets Sidney Deane (Wesley Snipes), a sassy basketball player who sees an opportunity to win some money, the duo starts their con game that ends up in a one-on-one match. Who will win, and who will take the money? 

You’ll have to watch to find out.

Best movies of the 2000s

6. Hardball (2001) — Baseball gambling movie based on a true story

• Director: Brian Robbins
• Box office earning – $44,102,389 
• Main cast: Keanu Reeves, Diane Lane, John Hawkes

The beginning of the new century brought us Hardball, a movie directed by Brian Robbins. The film was based on the book Hardball: A Season in the Projects by Daniel Coyle, which was based on his life.

While the movie’s initial budget was $32 million, it managed to earn $44 million at the box office (91.2% of the earnings came from the domestic box office) thanks to its witty and funny script. 

Unlike other sports betting movies, Hardball uses baseball gambling only for the atmosphere, focusing more on the main characters’ relationship.

That said, the story follows a gambler Conor O’Neill (Keanu Reeves), who can repay his debts only if he accepts to coach a fifth graders baseball team. This movie is a moving drama that will win all cinephiles’ hearts, even if they are not baseball fans.

7. Owning Mahowny (2003) — One of the most thrilling movies about gambling addiction

• Director: Richard Kwietniowski
• Box office earning – $1,271,244
• Main cast: Philip Seymour Hoffman, Minnie Driver, John Hurt  

Owning Mahowny is a thriller drama directed by Richard Kwietniowski. The movie was filmed on a small budget of $10 million. Despite its fantastic cast (Philip Seymour Hoffman, Minnie Driver, and John Hurt) and thrilling narrative, it earned only $1.2 million at the box office.  

Owning Mahowny was based on a true story about a bank employee from Toronto who stole money from his bank to feed his gambling addiction. 

This thrilling movie centers around Dan Mahowny (Philip Seymour Hoffman) and his gambling addiction. Unlike other flashy movies about counting cards, gambling, and betting, Owning Mahowny has a dark atmosphere that emphasizes on the obsession.

8. Two for the Money (2005) — Movie about the sports-gambling business based on a true story.  

• Director: D.J. Caruso 
• Box office earning – $30,526,509
• Main cast:  Matthew McConaughey, Al Pacino, Rene Russo

Two for the Money is a movie directed by D.J. Caruso, a man of many talents who dabbled in various film genres. 

This is one of the more expensive releases on our list of sports gambling movies. It was filmed with a $35 million budget and ended up earning a total of $30.5 million at the domestic and international box office. 

Fans of Matthew McConaughey and Al Pacino will enjoy watching this movie about a former college football star, Brandon Lang (McConaughey), and his partnership with Walter Abrams (Pacino), a gambling addict. 

Walter preys on the young Brandon, who soon becomes his winning machine, turning into his alter ego—an exclusive sports broker.

Best Gambler Movies of the Last Decade

9. Silver Lining Playbook (2012) — One of the most creative movies about mental illnesses and addiction

• Director: David O. Russell
• Box office earning – $236,412,453
• Main cast:  Bradley Cooper, Jennifer Lawrence, Robert De Niro  

Silver Lining Playbook is a romantic comedy-drama based on an equally successful novel by the same name. The movie was directed by David O.Russell, who started with a small budget of $21 million, managing to earn $236.4 million at the box office. 

As one of the more recent gambling movies, Silver Lining Playbook incorporates a more romantic approach to the subject, making it less dark. 

The story revolves around Pat Solitano (Bradley Cooper), who just came out of the mental institution. She is a strange girl called Tiffany (Jennifer Lawrence), who has an unnamed mental illness.

We also meet Pat’s father, Pat Sr. (Robert DeNiro). He suffers from an undiagnosed disorder that shows through his addiction to gambling and sports superstitions.

10. Uncut Gems (2019) — One of the best indie movies on gambling addiction and its consequences 

• Director: Benny Safdie, Josh Safdie 
• Box office earning: $50,023,780
• Main cast:  Adam Sandler, Julia Fox, Idina Menzel 

Uncut Gems is a dark comedy about a gambling addict, directed by the Safdie brothers (Joshua and Benjamin). 

As you already know, movies don’t necessarily need to be expensive to be effective, and Uncut Gems is the living proof of that. The movie’s initial budget was $19 million, and it earned $50 million at the domestic box office.

Uncut Gems is a new gambling movie that focuses on a gambling addict called Howard Ratner (Adam Sandler). He works as a jeweler with his girlfriend and employee Julia De Flore (Julia Fox). 

This chaotic tale follows Howard’s complex life full of bad choices and delusions, symbolized by a large black uncut opal. What’s more, Boston Celtics fans will be thrilled to know that Kevin Garnett made his feature debut in this movie by playing himself.

Honorable Mentions

Here are some honorable mentions that deserve a spot on our list.

11. The Lady Gambles (1949) — One of the best movies about casinos and gambling from the Golden Age of Hollywood

• Starring: Barbara Stanwyck, Robert Preston, Stephen McNally

Not many people have heard about this cinema gem directed by Michael Gordon. 

The Lady Gambles tells a story about Joan Phillips Boothe (Barbara Stanwyck). She is a gambling addict who struggles with her addiction which causes her to lose all her life savings. 

It is among the best movies about casinos featuring a woman as the lead.

12. The Gambler and the Lady (1952) — Movie about love, gangsters, and illegal gambling

• Starring: Dane Clark, Kathleen Byron, Naomi Chance

Patrick Jenkins and Sam Newfield directed this British crime movie that talks about gambling, casino nightclubs, gunfights with mobsters, and an American gambler who tries to get accepted by the British nobility.

The Gambler and the Lady differed from the typical Hollywood casino movies of the time because it was produced by Hammer Film Productions, known for their horror movies. 

13. The Gambler (1974) — Movie about the dark gambling obsession

• Starring:  James Caan, Paul Sorvino, Lauren Hutton

The story follows an English professor, Axel Freed, who loses control over his gambling addiction. Axel doesn’t play to win; he plays to feel the rush of energy and the excitement that gambling brings.

Besides losing his money constantly, he decides to borrow more from his family to satisfy his urges, despite being chased by the bad guys.

When it comes to top gambling movies, older movie fans probably remember this excellent adaptation. The younger audience might know the equally interesting 2014 remake. 

Keep in mind that this is not just a movie about gambling. It explores the dark and obsessive side of human nature and the dangers of gambling. The stunning ending scene of the film won’t leave you indifferent.

 14. Rounders (1998) — One of the best-known poker movies of all times

• Starring:  Matt Damon, Edward Norton, Gretchen Mol

Rounders is a 1998 movie directed by John Dahl that became a cult classic in the 2000s due to poker’s popularity. 

The story revolves around two law students, Mike McDermott (Matt Damon) and Lester “Worm” Murphy (Edward Norton), who play poker to pay off a debt. 

The two main characters are the complete opposites, with Mike being the honest player and Worm being a cheater. 

This Matt Damon gambling movie popularized poker terms like “flop,” “splash the pot,” and “nut straight.” 

One of the most notable characters in the movie was played by John Malkovich. He portrayed a Russian mobster called Teddy KGB. Many fans are still deliberating on the ending of the film. What was Teddy KGB holding during the final hand?

15. The Cooler (2003) — One of the best casino movies that talks about gambling curses and love

• Starring: William H. Macy, Maria Bello, Alec Baldwin. 

Directed by Wayne Kramer, The Cooler is not known for its flashy CGI effects and taking itself too seriously. In reality, casinos don’t hire “coolers” and are not led by the mafia. Instead, the movie brings us fantastic acting performances and many quotable dialogues. 

Bernie Lootz (William H. Macy), aka the cooler, is the main character in this fun take on casino movies. What’s a cooler? Cooler is the nickname the protagonist gets from his boss due to his “talent” for stopping people from winning bets by simply standing next to them. 

This interesting drama-romance follows Bernie’s life and his day-to-day job as a cooler in the Las Vegas casino. Once he falls in love, his cooling abilities disappear, which leads to a series of unpredictable scenarios. 

16. 21 (2008) — Movie about card counting inspired by a true story about six students who used math skills to cheat the dealers

• Starring: Jim Sturgess, Kate Bosworth, Kevin Spacey 

Robert Luketic directed a movie that was inspired by an intriguing true story about six students who used their card counting skills to cheat the casinos worldwide. 

The story follows the main character, Ben Campbell (Jim Sturgess). He is a student who becomes a part of a group that uses mathematical skills to cheat the casinos and win money led by an unconventional professor Mickey Rosa (Kevin Spacey).

This blackjack movie might be somewhat unrealistic and full of clichés. However, due to its atmosphere and a great soundtrack, it managed to earn an impressive $159.8 million at the box office (the initial budget was $35 million).

Moreover, the movie’s casting is also controversial, given that the actual students were Asian Americans, not white.

17. Molly’s Game (2017) — One of the most famous poker movies   based on a true biographical story

• Starring: Jessica Chastain, Idris Elba, Kevin Costner

This biographical drama, directed by Aaron Sorkin, talks about the life of Molly Bloom (Jessica Chastain), a “Poker Princess.” She was best known for organizing underground poker games. 

The story follows Molly’s life, her most exclusive poker games, and her final confrontation with the FBI, in addition to her sentence that might surprise you.

Like other great poker movies, Molly’s Game manages to show us the world of the high-stake bets, the glamour, and the danger surrounding it. This movie is a must-watch if you want to learn more about one of the most famous personas in the world of underground poker.

Fun fact, in reality, many Hollywood stars, including Leonardo DiCaprio, Ben Affleck, and Tobey Maguire (Player X), participated in the mentioned events. 

We’ll keep you posted if any new gambling movies from 2020 and on come out! Meanwhile, let’s talk about some of the most notable roles in movies about wagering, gambling, and betting. 

Many Hollywood actors and actresses became well-known to the audiences due to their exceptional performances. We’ll take a walk down memory lane to remember some of the best gambling characters that we learned to love or hate.   

Prominent Roles in the Movies About Betting

Now, let’s turn our attention to the best male and female roles.

Adam Sandler and Julia Fox in Uncut Gems  

Adam Sandler is an actor mostly known for his comedic roles in movies. He might not be a fan’s favorite since he’s been nominated 11 times for a Golden Raspberry Award.

Nevertheless, Sandler showed the world that he’s not just a comic actor. With his role in the dark comedy indie thriller called Uncut Gems, where he portrayed a gambling addict. His acting in this movie earned him many critical acclaims. 

It would be interesting to see Sandler in movies about blackjack, or poker, to see his final transformation from a movie jester to a serious actor (player). 

Unlike Sandler, Julia Fox is a young actress that made her film debut in Uncut Gems. Her role in the film brought her a nomination for the Breakthrough Actor Award in 2019. 

Paul Newman, Tom Cruise, and Mary Elizabeth Mastrantonio in The Color of Money 

While the Color of Money is not one of the best Paul Newman movies (supporting) roles, the film did manage to bring back one interesting character to life. He played the fascinating Edward “Fast Eddie” Felson from the film’s predecessor, The Hustler (1961).

Paul Newman was one of the most famous American actors, director, and race car driver. He won various awards during his lifetime, from the Academy Award to the BAFTA Award.

Fun fact, Newman did a screen test together with another Hollywood rebel, James Dean, for a 1955 movie, East of Eden (Dean’s last film), but he didn’t get the part. 

A year later, he got his major movie role as Rocky Graziano in the movie Somebody Up There Likes Me. It was initially intended for Dean, but he tragically passed away. 

Tom Cruise, who’s no stranger to movies with gambling or taking on impossible missions, was Newman’s co-star in The Color of Money. 

Cruise, who was 24 at the time, already had an impressive career behind him, with his role in Ridley Scott’s Legend (1985) and Tony Scott’s Top Gun (1986). 

Today, Cruise is one of the highest-paid actors that’s still actively working on movies and his cult classic-Mission: Impossible series.

Mary Elizabeth Mastrantonio might not be known for her roles in gambling Hollywood movies. However, The Color of Money brought her an Oscar nomination for the Best Supporting Actress. 

This American actress and singer is mainly known among the older audience for Lady Marian’s role in Robin Hood: Prince of Thieves (1991).

We should also mention that her first role on screen was beside Al Pacino in the movie Scarface (1983), where she portrayed Tony Montana’s sister Gina.

Keanu Reeves in Hardball

We could easily picture Keanu Reeves in various film genres, from the Las Vegas-themed movies to dark action SF movies and even comedies. Reeves is one of the most likable Hollywood actors that’s also known for his writing and philanthropy.

He made his feature debut in 1986 in the movie Youngblood, but today’s audience probably knows him for his cult roles of Neo (Matrix) and John Wick.  

Richard Dreyfuss and Jennifer Tilly in Let it Ride

A famous real-life gambler, Jennifer Tilly, played a notable role in the movie Let it Ride, alongside her co-star Richard Dreyfuss, portraying a woman called Vicki. 

When she’s not gracing the audience with her distinctive voice, Tilly plays poker. She also worked on many movies about poker, like Deal (2008) and the documentary Poker Queens (2020).

That said, her most prominent movie role is the one of Tiffany Valentine from the horror franchise Child’s Play (1998), as Chucky’s partner. 

Richard Dreyfuss is no stranger to Hollywood classic movies. Most people remember him for his roles in American Graffiti (1973), Jaws (1975), and Close Encounters of the Third Kind (1977).

He was also the youngest person to win the Academy Award for Best Actor in 1978 for his role in The Goodbye Girl (1977). 

William H. Macy in The Cooler

The main character of one of the top casino movies from our list is portrayed by a well-known Hollywood actor, William Hall Macy. 

Macy is known for his roles in various independent movies, as well as high-budget films. He was nominated for the Best Supporting Actor for his role in Fargo (1996), and he managed to win 2 Emmy Awards and 4 Screen Actors Guild Awards. 

John Malkovich and Gretchen Mol in Rounders 

John Malkovich played a significant role in one of (if not) the best movies about poker. His portrayal of the Russian mobster called Teddy “KGB” was one of the highlights of the film, already filled with talented actors like Matt Damon and Edward Norton. 

Malkovich is also known for his extraordinary performances in the Dangerous Liaisons (1988), Being John Malkovich (1999), and Shadow of the Vampire (2000).

Gretchen Mol is mainly known for her role in Boardwalk Empire (as Gillian Darmody). Nevertheless, you’ve probably seen her in the famous western movie 3:10 to Yuma (2007) and the independent drama Manchester by the Sea (2016).

James Caan and Lauren Hutton in The Gambler

When it comes to gambling movies, you won’t find a better actor than James Caan, who managed to capture some of the darkest traits of human nature. 

Caan is also known for his role in The Godfather as Sonny Corleone, so he’s no stranger to the human psyche. You can also probably remember his role in Stephen’s King adaptation, Misery (1990).  

In the movie, the main female character (Billie) was played by an American actress and model, Lauren Hutton, known for her role in American Gigolo (1980). 

Barbara Stanwyck in The Lady Gambles

Barbara Stanwyck was an American model, actress, and dancer who was notable for her many movie and television roles. 

When it comes to movies about betting, her portrayal of Joan in The Lady Gambles was very strong and realistic. The trait for which she was known in Hollywood. 

Kathleen Byron in The Gambler and the Lady

Kathleen Byron was a famous British actress known for her role as the neurotic nun Ruth in Black Narcissus (1947) and Pat in a 1952 movie called The Gambler and the Lady.

She also portrayed Mrs. Goddard in Emma (1996) and Old Mrs. Ryan in Saving Private Ryan (1998), her last movie role.  

Jessica Chastain in Molly’s Game

You might know Jessica Chastain for her notable role of Molly in one of the best poker movies based on a true story. 

However, Chastain is an American actress and producer who also won a Golden Globe Award for her role in Zero Dark Thirty. Likewise, she received a nomination for the Best Supporting Actress for her role in the movie The Help (2012). 

She’s also known for her feminist views and movie roles. 

Best Movie Quotes About Betting and Odds

Many movies about betting are remembered for their notable dialogues that are often quoted by the audience. Here are some of the best ones. 

Croupier (1998) — “Gambling’s not about money… Gambling’s about not facing reality, ignoring the odds.”

Croupier is a movie directed by Mike Hodges that talks about a writer named Jack Manfred (Clive Owen). It’s a story about Clive Owen trying to fight writer’s block by getting a job as a croupier at a casino. 

One of the most memorable quotes from the movie includes a dialogue between Jack and a gambler called Marion (Gina McKee), who wants him to help her with a casino heist.

Casino Royale (2006) — “I think your odds are improving, Mr. Bond.” 

Casino Royale (2006) is a famous James Bond movie about casino cheating and high stake-poker games. The film was directed by Martin Campbell, while Bond was played by a British actor Daniel Craig. 

The movie has some of the best casino scenes and some of the most iconic movie quotes.   

The Color of Money (1986) — “Money won is twice as sweet as money earned.”

The Color of Money (1986) might not be the absolute best Scorsese movie. Still, the dialogue about the money between Eddie Felson (Paul Newman) and Vincent Lauria (Tom Cruise) is most definitely one of the most quoted movie lines.

Uncut Gems (2019) — “I made a crazy risk, a gamble, and it’s about to pay off.”

One of the unforgettable gambling quotes from movies includes Howard Ratner’s (Adam Sandler) line from the film Uncut Gems (2019). This line perfectly describes the character’s addiction to gambling. 

Around the World in 80 Days (1956) — “An Englishman never jokes about a wager, sir.”

Michael Anderson’s Around the World in 80 Days is a movie based on a famous novel by Jules Verne. This Hollywood classic brought to screen the epic tale of Phileas Fogg (Davin Niven) and his wager that he would be able to make a trip around the world in 80 days. 

Ocean’s Thirteen (2007) — “Oh, I don’t lose. People who bet on me to lose. And they lose big.”

When we talk about great gambling movies, we must not forget about Steven Soderbergh’s Ocean’s Thirteen. The movie’s cast includes some of the biggest Hollywood stars like George Clooney, Brad Pitt, and Matt Damon. 

And what makes a great movie? Unforgettable and catchy quotes like Al Pacino’s line about betting.  

Mississippi Grind (2015) — “You know why? I don’t care about winning.”

Mississippi Grind is a well-known Ryan Reynolds gambling movie, written by the duo Anna Boden and Ryan Fleck. The story follows two gamblers, Gerry (Ben Mendelsohn) and Curtis (Ryan Reynolds), on their road trip to get the money. 

This quote explains perfectly one’s addiction to the game, where it’s more important to play than to win.

Conspiracy Theory (1997) — “The Vietnam War was fought over a bet that Howard Hughes lost to Aristotle Onassis.”

Although Richard Donner’s Conspiracy Theory is not a movie about counting cards, casinos, or gambling, it contains one of the most iconic quotes about betting. 

Jerry Fletcher (Mel Gibson) is a taxi driver who believes that the government is covertly responsible for various world events. For instance, he believes that the Vietnam War started due to a bet and that the Grateful Dead is part of the British Secret Service.

Walk Like a Man (1987) — “You’re the only man whoever bet on a horse that started from a kneeling position.”

On the list of movies with gambling as the main topic, we have one comedy that’s not focused on gambling addiction—Melvin Frank’s Walk Like a Man. Nevertheless, one of the movie’s famous quotes includes Rhonda Shand’s (Colleen Camp) reference to horse racing. 

Oscar and Lucinda (1997) — “We bet that there is a God.”

Oscar and Lucinda is a romantic drama set in the early 19th century that talks about two people, Oscar (Ralph Fiennes) and Lucinda (Cate Blanchett), who are both passionate gamblers. 

The movie’s most notable quote is Oscar’s famous line about the ultimate gamble — God’s existence. The quote was inspired by Pascal’s Wager. 

Conclusion

Good gambling movies often take us on a journey through the human psyche, exploring the origins of greed. While some films speak only about the game’s glamourous parts, others go much deeper by focusing on gambling addiction.

Gambling has been a part of our culture for centuries. But what happens when this seemingly fun pastime becomes an obsession?