Top 10 Gambling Movies Ever

By BestOdds Analyst | August 10, 2021 10:31 AM

The excitement that surrounds gambling is something every bettor feels, especially when they take that little extra risk for a sweet reward.

And this is precisely what makes gambling films so exciting! The spin of the slots, the quick changing hands of dealers, the extravagance—it feels like you’re there yourself.

So if you want to feel like you’re in a real casino putting it all on the table, read on to check out our top 10 favorite gambling movies ever.

1. California Split (1974)

First on the list is a classic—California Split, directed by Robert Altman. This dramedy not only highlights the highs but the lows of gambling as well.

Bill (George Segal) and Charlie (Elliott Gould) become friends over a mutual love of gambling. The story sees the two getting hooked into the game to the point of selling their possessions when convinced they’re on a hot streak.

We won’t give away too much to enjoy it yourselves, but this film is one to watch. It includes a great message touching on gambling addictions and knowing when to quit.

2. Casino (1995)

Martin Scorsese hit the mark with this classic intricate drama chronicling the inner workings of Sin City’s underground mob dealings.

Robert De Niro is Ace, a gangster trying to turn straight while working at a mobbed-up casino. On the other side, we have Joe Pesci and Sharon Stone playing his hot-headed pal and the woman he can’t trust, respectively.

Some may say this isn’t a gambling film, but the depiction of Vegas within Casino speaks for itself. We had to include Casino on this list because it simply would not be complete without it.

3. Molly’s Game (2017)

Now, this is a personal favorite that is an absolute must-watch. Aaron Sorkin’s directorial debut took the 2014 memoir of Molly Bloom and stuck it on the big screen in one of the best biographical crime dramas of the 2000s.

Molly (Jessica Chastain) starts as a world-class mogul skier with quite the overbearing father/coach. After an injury at an Olympic qualifiers event, she quits, abandons law school, and somehow ends up in LA.

Long story short, she makes connections and somehow becomes involved and later the ringleader of an underground poker ring involving movie stars, investment bankers, sports players, and more.

The best part about this film? It all happened.

4. High Roller: The Stu Ungar Story (2003)

Alternatively known as “Stuey,” this low-budget production is another biopic that highlights the highs and lows of gambling.

The film flashes back to the three-time World Series of Poker winner, Stu Ungar (Michael Imperioli), during his prime years.

Ungar then chronicles his life to a stranger telling the story of an intelligent man with promise who becomes addicted to drugs. His excellent poker skills bankrolled his addiction throughout the heart-wrenching tale.

5. The Cincinnati Kid (1965)

This Depression-era drama takes poker to a new level as it depicts a marathon game of poker while still including everything you need for a great gambling film. There are guns, women, action, betrayal, and of course, shady, underhanded moves.

The story centers on “The Kid” (Steve McQueen), a detached hotshot with a lot of confidence. Despite his friends advising against it, he decides to take on Lancey Howard (Edward G. Robinson), known as “The Man.”

As this fast-paced thriller unravels, the world of gambling unravels with it. The riveting rivalry between The Kid and The Man comes to a close with a phenomenal ending.

However, the director Norman Jewison wanted to end the film at a different point than the producer. So keep an eye out for which ending you get on the version you watch.

6. Ocean’s Eleven (2001)

Now, I know what you’re thinking—this is a heist movie, not a movie on gambling. But this iconic film is centered around a plot to rob not just the Bellagio but the Mirage and the MGM Grand as well.

This 2001 remake exuded the sleek, jazzy, and cocky spirit of Vegas for the first time. Not to mention it has a star-studded cast, including George Clooney, Brad Pitt, and Julia Roberts.

Director Steven Soderbergh took this film to new heights and created a whole new market for gambling films with the Ocean’s series. There’s even an all-female remake known as Ocean’s 8 with Sandra Bullock playing Danny Ocean’s estranged sister, Debbie Ocean.

So, you all know what that means—it’s time for a movie marathon.

7. 21 (2008)

21 is another “based on a true story” drama, this time directed by Robert Luketic. The story is based on the novel “Bringing Down the House” by Ben Mezrich.

MIT maths professor Micky Rosa educates six of his students on how to count cards to win blackjack. Star student Ben (Jim Sturgess) joins in hopes of making enough money to attend Harvard Medical School in the fall.

This is before Vegas upgraded its systems to ensure there is no more counting cards, amongst other strategies. But back in the early 2000s, the six students took many Las Vegas casinos for millions.

This movie is a winner winner chicken dinner (you’ll get that reference once you watch the film).

8. Casino Royale (2006)

The only thing better than a gambling movie is a gambling movie with James Bond. Martin Campbell’s debut of Daniel Craig as 007 was the highest-grossing Bond film to appear on the screen (at the time).

Casino Royale sees Bond (Craig) playing an extremely high stakes poker game against Le Chiffre (Mads Mikkelsen), a terrorist financier.

Not only does this movie have action and adventure, but it also has some pretty excellent bluffing strategies and is one of the largest hands won in the cinematic gambling universe. If you haven’t seen it yet, it is an absolute must.

9. The Gambler (1974)

The Gambler is based on (problematic) screenwriter James Toback’s own life and struggles with a gambling addiction. The film is centered on Axel (James Caan), an English professor obsessed with not gambling but danger.

Axel makes bets not for the win nor the risk but for the fun of losing. He argues that is what truly motivates gamblers like him. After losing multiple times and causing trouble in all of his close relationships, he continues to spiral throughout the film.

Again, we don’t want to give too much away, but this crime drama is one to put on the list. Just don’t watch the 2014 remake with Mark Wahlberg… trust us.

10. Rounders (1998)

If you’re looking for a gambling movie that has everything, Rounders is the one. A “rounder” by definition is a person who travels from place to place looking for high-stakes card games.

In this case, it’s poker. The story follows Mike McDermott (Matt Damon) and his friend Lester (Edward Norton) as they try to settle their gambling debts with a Russian mobster named KGB (John Malkovich).

Rounders has been praised for its authenticity in respect to the actual playing of poker, but even if you’re not into gambling, this film is an overall winner.

There you have it folks! The top 10 gambling movies ever. We hope you enjoy watching them, and let us know if you think we missed any.