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Quick answer: the best gambling movies are The Sting (1973), Casino (1995) and Rounders (1998), with The Hustler and The Cincinnati Kid close behind. Below are our 20 picks with year, director and stars (each checked in two film databases), the best poker and sports gambling movies, the real odds behind four famous scenes, and the best gambling books.
The best gambling movies at a glance
| # | Film | Year | Game | Director | Starring |
|---|---|---|---|---|---|
| 1 | The Sting | 1973 | Con game | George Roy Hill | Paul Newman, Robert Redford, Robert Shaw |
| 2 | Casino | 1995 | Casino | Martin Scorsese | Robert De Niro, Sharon Stone, Joe Pesci |
| 3 | Rounders | 1998 | Poker | John Dahl | Matt Damon, Edward Norton, John Turturro |
| 4 | The Hustler | 1961 | Pool | Robert Rossen | Paul Newman, Jackie Gleason, Piper Laurie |
| 5 | The Cincinnati Kid | 1965 | Poker | Norman Jewison | Steve McQueen, Edward G. Robinson, Ann-Margret |
| 6 | Uncut Gems | 2019 | Betting | Josh Safdie, Benny Safdie | Adam Sandler, LaKeith Stanfield, Julia Fox |
| 7 | Molly’s Game | 2017 | Poker | Aaron Sorkin | Jessica Chastain, Idris Elba, Kevin Costner |
| 8 | California Split | 1974 | Poker, betting | Robert Altman | George Segal, Elliott Gould, Ann Prentiss |
| 9 | The Gambler | 1974 | Addiction | Karel Reisz | James Caan, Paul Sorvino, Lauren Hutton |
| 10 | Owning Mahowny | 2003 | Addiction | Richard Kwietniowski | Philip Seymour Hoffman, Minnie Driver, John Hurt |
| 11 | Casino Royale | 2006 | Texas hold’em | Martin Campbell | Daniel Craig, Eva Green, Mads Mikkelsen |
| 12 | Hard Eight | 1996-97 | Casino | Paul Thomas Anderson | Philip Baker Hall, John C. Reilly, Gwyneth Paltrow |
| 13 | The Cooler | 2003 | Casino | Wayne Kramer | William H. Macy, Alec Baldwin, Maria Bello |
| 14 | Mississippi Grind | 2015 | Poker | Anna Boden, Ryan Fleck | Ben Mendelsohn, Ryan Reynolds, Sienna Miller |
| 15 | 21 | 2008 | Blackjack | Robert Luketic | Jim Sturgess, Kevin Spacey, Kate Bosworth |
| 16 | Two for the Money | 2005 | Sports betting | D.J. Caruso | Al Pacino, Matthew McConaughey, Rene Russo |
| 17 | Bugsy | 1991 | Las Vegas | Barry Levinson | Warren Beatty, Annette Bening, Harvey Keitel |
| 18 | The Color of Money | 1986 | Pool | Martin Scorsese | Paul Newman, Tom Cruise, Mary Elizabeth Mastrantonio |
| 19 | High Roller: The Stu Ungar Story | 2003 | Poker | A. W. Vidmer | Michael Imperioli, Renee Faia, Michael Nouri |
| 20 | Eight Men Out | 1988 | Sports betting | John Sayles | John Cusack, Clifton James, Michael Lerner |
Hard Eight is listed as 1996 on Letterboxd and 1997 on TMDB, so we show both years. The ranking is our own opinion.
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The 10 greatest gambling movies
1. The Sting (1973)
A novice con man teams up with a master to avenge a murdered friend by swindling a fortune from a big-time mobster. It is the gold standard because the audience gets conned along with the villain, and every gambling scene is part of the trick.
2. Casino (1995)
Martin Scorsese’s Las Vegas epic follows two best friends, a casino executive and a Mafia enforcer, fighting over a gambling empire and a fast-living socialite. It is based on Nicholas Pileggi’s book, and Pileggi co-wrote the screenplay. No film shows better how a casino counts, watches and protects its money.
3. Rounders (1998)
Poker player Mike McDermott loses his money to the gangster Teddy KGB, promises to quit, then gets pulled back in when his friend Worm leaves prison owing money to the wrong people. It is the best poker movie because the players talk and think like real players. If you want to learn the game behind it, our guide on how to win at poker is a good next step.
4. The Hustler (1961)
Small-time pool hustler Fast Eddie Felson has the talent but not the temperament, and challenges the legendary Minnesota Fats to a high-stakes match. It is less about pool than about what it costs to keep betting on yourself.
5. The Cincinnati Kid (1965)
An up-and-coming stud poker player takes on the long-time master of the game, Lancey Howard. The final hand is the most argued-about in movie history; we check its odds below.
6. Uncut Gems (2019)
A New York City jeweler chases the windfall of a lifetime through a run of high-stakes bets while debts close in. It is the most stressful film on this list and the most honest about how chasing losses feels.
7. Molly’s Game (2017)
Molly Bloom, a former Olympic hopeful skier, builds a high-stakes international poker game and becomes the target of an FBI investigation. Aaron Sorkin’s film is based on Bloom’s 2014 memoir of the same name.
8. California Split (1974)
Robert Altman’s loose, funny film follows two gambling buddies on a streak in search of the big payday. It catches the highs and the flat, empty mornings better than most bigger films.
9. The Gambler (1974)
New York English professor Axel Freed looks respectable, but a severe gambling addiction is destroying him. It is a hard, unglamorous watch and one of the clearest films about compulsive gambling.
10. Owning Mahowny (2003)
Dan Mahowny is a rising star at a Toronto branch of the Canadian Imperial Bank of Commerce, and a quiet, workaholic gambler. The film plays his addiction without any drama, which makes it more frightening.
Best poker movies
Poker movies are the biggest group of gambling films, and the best ones get the table talk right. Our top poker movies, in order:
- Rounders (1998): the table talk sounds like a real game.
- The Cincinnati Kid (1965): five-card stud and the most famous final hand.
- Molly’s Game (2017): the business of running a high-stakes game.
- Casino Royale (2006): James Bond plays Texas hold’em against Le Chiffre in Montenegro.
- Mississippi Grind (2015): a down-on-his-luck gambler and a younger poker player on a road trip to a big game in New Orleans.
- High Roller: The Stu Ungar Story (2003): based on the true story of poker legend Stu “The Kid” Ungar; our list of the richest gamblers covers players who kept their money.
- Lucky You (2007): a professional player tries to win the World Series of Poker.
If a film hand leaves you wondering what beats what, our poker hand rankings chart has every hand with its odds.
Best sports gambling movies
- Two for the Money (2005): a former college athlete teams up with a sports consultant to handicap football games for high-rolling gamblers.
- Eight Men Out (1988): underpaid Chicago White Sox players agree with gamblers to throw the World Series.
- Uncut Gems (2019): a jeweler stacks his whole life on a series of high-stakes bets.
Real sports betting is slower and duller than any of these films. Our sports betting tips explain what actually matters, such as the bookmaker’s margin.
We checked the odds in four famous scenes
Movies love impossible luck. We worked out the odds behind four well-known scenes ourselves. The scene details come from two sources each (listed under How we checked); the sums are ours.
| Film and scene | What happens | Our sum |
|---|---|---|
| Casino Royale: the final hand | The board shows two aces, 8♠, 6♠ and 4♠. One player has a flush, one has eights full, Le Chiffre has aces full (A-6), and Bond’s 7♠ 5♠ makes a straight flush. | Of the 1,081 two-card hands an opponent could hold, only one (7♠ 5♠) makes a straight flush on that board: 1 in 1,081 for a given player, before you add three other monster hands in the same pot. |
| The Cincinnati Kid: the last hand | The Kid’s aces full of tens loses to Lancey Howard’s straight flush in diamonds. | A five-card straight flush (counting royal flushes) comes up in 40 of 2,598,960 possible hands, or 1 in 64,974. Needing it on the one hand where your opponent has aces full makes it far rarer. |
| Casablanca (1942-43): roulette | Rick has the croupier let the number 22 come up twice so a refugee couple can win money for exit visas. | Hitting one number twice in a row is 1 in 1,369 on a single-zero wheel (37 × 37) and 1 in 1,444 on a double-zero wheel. In the film the wheel was rigged. |
| 21: the Monty Hall question | A maths professor (Kevin Spacey) asks Ben whether to switch doors in the Monty Hall game show puzzle. | We simulated 1,000,000 games on 1 November 2026: switching won 666,906 times (66.7%) and sticking won the rest (33.3%). Switching is right. |
For the maths behind casino games, see our guides to roulette odds and poker maths. Card counting, the method behind 21, is explained in our card counting guide.
Best gambling books
Several of the best gambling movies started as books. These are the gambling books we would read first:
| Book | Author | Year | Why read it |
|---|---|---|---|
| Beat the Dealer | Edward O. Thorp | 1962 | The book that showed card counting could beat blackjack. |
| Bringing Down the House | Ben Mezrich | 2002 | The MIT blackjack team story that became the film 21. |
| Casino: Love and Honor in Las Vegas | Nicholas Pileggi | 1995 | The reporting behind the Scorsese film. |
| Positively Fifth Street | James McManus | 2003 | A magazine writer plays the World Series of Poker Main Event. |
| Molly’s Game | Molly Bloom | 2014 | The memoir behind the Sorkin film. |
| The Biggest Bluff | Maria Konnikova | 2020 | A psychologist learns poker from scratch. |
Best sports betting books
| Book | Author | Why read it |
|---|---|---|
| Sharp Sports Betting (2001) | Stanford Wong | A long-standing basics book on how betting lines and value work. |
| The Logic of Sports Betting | Ed Miller and Matthew Davidow | How sportsbooks set and move lines. |
| Weighing the Odds in Sports Betting | King Yao | The maths of finding value. |
| Trading Bases | Joe Peta | A story-led read about a trader who became a baseball bettor. |
Films and books make big wins look normal. They are not: in real gambling the house edge wins over time. If gambling has stopped being fun, see our responsible gambling page for help and tools.
Gambling Movies FAQ
What is the best gambling movie of all time?
Our pick is The Sting (1973), directed by George Roy Hill and starring Paul Newman and Robert Redford. Casino (1995) is the best film about how a casino works, and Rounders (1998) is the best poker movie.
What is the best poker movie?
Our pick is Rounders (1998), with Matt Damon and Edward Norton. The Cincinnati Kid (1965) and Molly’s Game (2017) are the next best.
Which gambling movies are based on a true story?
High Roller: The Stu Ungar Story is based on the life of poker player Stu Ungar, Molly’s Game is based on Molly Bloom’s memoir, Casino is based on Nicholas Pileggi’s book, and 21 is based on Ben Mezrich’s book about MIT students who counted cards. Eight Men Out is about the White Sox players who threw the World Series.
Could the Casino Royale final hand really happen?
Only just. On that board, exactly one two-card hand out of 1,081 makes Bond’s straight flush, and three other players also had to hold a flush or a full house. It makes great cinema and terrible poker maths.
What are the best gambling books?
Start with Beat the Dealer by Edward O. Thorp for blackjack, Positively Fifth Street by James McManus for poker, and Sharp Sports Betting by Stanford Wong for sports betting.
How we checked
- Film year, director and main cast: Letterboxd and TMDB. Where they differ (Hard Eight, Casablanca) we show both years. Casino’s source book and Pileggi’s screenplay credit: both databases.
- Casino Royale final hand: PokerNews and CommanderBond.net. They disagree on the suit of the second ace, which does not change our sum.
- The Cincinnati Kid final hand: Filmsite and The Straight Dope.
- Casablanca roulette scene: Film Threat and SparkNotes.
- 21 and the Monty Hall problem: Computational Complexity blog and UC Santa Barbara.
- Books, authors and years: Open Library plus publisher or review pages (Simon & Schuster, Book Riot, PokerNews, Bookishelf). We leave out a year where we found only one source.
- All odds sums and the Monty Hall simulation are our own.
Last checked: 1 November 2026, when we worked out the odds behind four famous scenes ourselves (including a 1,000,000-game Monty Hall simulation) and checked each film’s year, director and cast in Letterboxd and TMDB.
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