Top 10 Gambling Movies of All-Time

Gambling is a subject that fascinates people all over the globe. With this being the case, it’s no wonder why there are so many different gambling-related and/or poker movies out there.

As cinema has changed over the decades – and gambling evolving so fast in the past few years, it’s been fun to see the different types of movies studios have churned out in relation to gambling.

Of course, some of these movies stand out above the rest and have become classics within the genre. Others have shown they have the staying power to truly affect a generation, as well as make little known actors into legends in their own right (Matt Damon in “Rounders” and Robert De Niro in “Casino” stand out as some).

Without further adieu though, here is a look at some the gambling films that have earned their right to be on this particular Top 10 list.  Enjoy minions, muhahahahahaahhaa (attempt at sinister laugh)!

1. “Rounders” (1998)

No gambling movie ever been as influential as “Rounders”. Rounders became a huge inspiration to poker players everywhere, and brought many new people to the game including 2003 WSOP champion Chris Moneymaker. In this film, Matt Damon plays Mike McDermott who uses poker as a means of paying his law school tuition. Unfortunately for McDermott, he loses his $30,000 bankroll in one hand to Russian mobster Teddy KGB, which prompts him to quit poker. But McDermott is eventually sucked back into the underground poker world by his old friend Worm (Edward Norton Jr.). He must then try to balance his poker career with his friend Worm’s debt problems, an unhappy girlfriend, and a looming rematch with Teddy KGB.

2. “Casino” (1995)

Behind the glitz and glamour, casinos have always carried a tough, mobster reputation. And the 1995 film “Casino” did a great job of characterizing this reputation through the Frank Rosenthal-based character Sam “Ace” Rothstein. Rothstein, who is played by Robert DeNiro, runs the Stardust casino for the mob while aided by fellow mobster and friend Nicky Santoro (Joe Pesci). The stakes get raised when Santoro and Rothstein’s relationship becomes strained, Rothstein’s wife Ginger (Sharon Stone) spirals into depression and substance abuse, and Sam’s actions come into question by the very mob he works for.

3. “The Gambler” (1974)

Gambling addiction is a well-known problem within the gambling community. And you’d think that James Caan’s character Axel Freed would understand this better than anybody since the New York City University professor preaches against gambling addiction. However, Freed’s familiarity with the subject does nothing for him when he falls victim to addiction. After obsession takes over, Freed is at the mercy of loan sharks and enforcers who will do anything to get their money back. No gambling movie has managed to capture the dangers of the betting world as well as “The Gambler”.

4. “Owning Mahowny” (2003)

Sticking with the theme of gambling addiction, “Owning Mahowny” portrays the real life story of bank clerk Brian Molony who embezzled over $10 million to feed his gambling addiction. Dan Mahowny, played by Philip Seymour Hoffman, is a Toronto banker who is given access to large bank accounts after a big promotion. Unfortunately, his gambling addiction grows along with the size of the bank accounts he manages. This leads him to skim account funds for Atlantic City gambling trips while attempting to hide the truth from his girlfriend Belinda (Minnie Driver) and the bank. It’s amazing how well Owning Mahowny depicts the highs and lows of Mahowny’s compulsive gambling problem while staying true to the original story.

5. “21” (2008)

Facing $300,000 in Harvard Medical School tuition fees, Ben Campbell (Jim Sturgess) hopes to win the Robinson Scholarship which would provide him with free tuition. But Campbell begins to realize that there may be a much quicker way to earn the money after his math professor Micky Rosa (Kevin Spacey) approaches him with a proposition. Soon, Campbell joins Rosa’s unstoppable MIT blackjack team in counting cards and earning mountains of cash. But their card counting practices don’t go unnoticed as ruthless casino security chief Laurence Fishburne is hot on their trail. This movie combines suspense and danger along with something people have always dreamed of – beating the house edge!

6. “The Cooler” (2003)

It’s hard finding many comedies within the gambling movie genre, so “The Cooler” is definitely worth mentioning. This film takes a humorous look at Bernie Lootz (William H. Macy) whose luck is so bad that nobody can win when he’s around. Seeing as how he has such a special “skill”, Lootz is hired by a major casino as a “cooler”, or person who cools down gamblers on a hot streak. But when Lootz falls in love with a casino waitress, he suddenly turns losers into winners, and subsequently draws the ire of casino owner Shelly Kaplow (Alec Baldwin). While The Cooler may not satisfy those looking for a more serious take on betting, it is a breath of fresh air for those who are searching for a light-hearted gambling movie.

7. “Croupier” (1998)

Jack Manfred (played by Clive Owen) has no intentions of being anything more than a novelist. However, his lack of success leads Manfred to begrudgingly take a croupier job until his writing takes off. Along the way, Manfred begins to lose himself in the casino world before eventually becoming fully immersed. His girlfriend Marion (Gina McKee) drifts away from Jack, but he is hardly deterred as Manfred is side-tracked by his contemplation of becoming an inside man for a casino heist. In addition to telling the compelling story of the temptations Manfred must resist, “Croupier” also does a solid job of portraying how real casinos operate.

8. “High Roller: The Stu Ungar Story” (2003)

2003 was a good year for gambling films since “High Roller: The Stu Ungar Story” also came out this year. As the name suggests, The Stu Ungar Story tells the tale of one of history’s most talented poker and gin rummy players in Stu Ungar. Ungar is only the second person ever to win the WSOP Main Event 3 times, and is widely considered to be the best gin rummy player ever. Unfortunately, Ungar’s arrogant attitude and drug addiction diminished his accomplishments; prolonged drug addiction would lead to his fatal heart attack in 1998. Controversial or not, Stu Ungar’s tale is definitely worth telling, and this film does an exceptional job of taking audiences from his days as a Manhattan card prodigy to his achievements on poker’s biggest stage.

9. “Casino Royale” (2006)

While Casino Royale may not fit the traditional gambling movie model, it certainly contains enough betting elements to land amongst the top 10 all-time gambling films. MI6 agent James Bond (Daniel Craig) must infiltrate a high-stakes Texas Hold’em poker tournament in order to defeat terrorist and international banker Le Chiffre. After initially being out-played by Le Chiffre, Bond must find a way to buy back into the tournament and defeat his adversary. In addition to the poker tournament, Casino Royale provides an exceptional display of action to supplement the gambling. This film reinvigorated the whole James Bond movie franchise.

10. “The Sting” (1973)

The Sting’s greatest attribute is its ability to tie an interesting plot in with the gambling world. In addition to this, the duo of Paul Newman and Robert Redford bring two of Hollywood’s greatest actors onto the same screen in this gambling-related classic. “The Sting” revolves around John Hooker (Redford) and Henry Gandorf’s (Newman) attempt to con high stakes gambler Doyle Lonnegan (Robert Shaw) through horse racing. Besides presenting an intricate, yet easily understood plot, The Sting does a good job of giving viewers an excellent look at horse racing.