The Best Gambling Movies | Dallas Observer

Movies are always a gamble. A writer bets that the story they’re writing is one that people will want to hear. A director bets that they’ve chosen the right crew to tell that story. Actors make bets with every choice they make on set — are they being overly emotive or too reserved? Certainly, studios are always making bets with how they spend their money and how audiences will react. Remember, someone bet that people would actually want to see a film based on Cats.

Audiences also are always making bets. They take a risk when choosing what film they buy a ticket for (or these days, what they rent online). Will it be worth the 12 bucks they could’ve spent on literally anything else? There’s always a bet involved when deciding what movies you watch with a group. If it’s your turn to pick a movie on movie night, you’re betting on something that won’t leave any of your friends or family members regretting their time.

We like watching movie characters take bets, risking it all for a big payoff. Watching fictional characters gamble away their lives allows us to enter into a world of high risks and heavy rewards without having to take the chances ourselves.

If you don’t want to risk going to a casino during a pandemic, and even if you don’t know how to play poker, here are some of our favorite gambling movies to watch that can tide you over.

The Hustler (1961)
The Hustler is the Citizen Kane of gambling movies, and Paul Newman gave one of his most remembered film performances ever as “Fast Eddie,” the serial gambling addict for whom winning was never enough. Newman was the rare movie star who could exude sadness, loneliness, weariness and charisma all at once, and The Hustler is a crowd pleaser that goes to some surprisingly dark places.

The Color of Money (1986)
A 25-year gap between two films in the same franchise usually isn’t a good sign, but thankfully Newman’s return to the Fast Eddie character was well worth the wait. This time, Eddie is the mentor who teaches the trade to a young hustler played by Tom Cruise (who never did anything else, did he?). The satisfying follow-up was the film that finally earned Newman an Academy Award for Best Actor.

California Split (1974)
This buddy movie classic is a surprisingly affectionate look at how friendships are formed and destroyed by the addictive nature of gambling. Like a great round of Texas hold’em, the partnership between Bill Denny (George Segal) and Charlie Waters (Elliot Gould) is awe inspiring and exciting, yet was never made to last.

Leaving Las Vegas (1995)
Believe it or not, there was a time when Nicolas Cage didn’t make 15 direct to VOD movies each year and could actually channel his performances into real characters, not self-parodical caricatures. Cage won the Oscar for Best Actor for his heartbreaking performance as a suicidal screenwriter tormented by alcoholism and an addiction to gambling.

Rounders (1998)
Matt Damon doesn’t look like he could pull a poker face to save his life, and Edward Norton’s signature smirk would probably give away any leads he might have, but if you can suspend your disbelief for two hours, Rounders is a damn exciting movie about two hot shots who get in over their head when they have to pay off a Russian mobster (John Malkovich).

Hard Eight (1996)
A lot of Hollywood movies tend to fantasize gambling as a thrill-a-minute, exhilarating experience, but 1996’s Hard Eight shows a different side, one with a lot more careful strategy, stuffy hotel rooms, and seedy side characters. Directed by the great Paul Thomas Anderson, this neo-noir classic follows a chance encounter between a veteran card player (Phillip Baker Hall) and a penniless orphan (John C. Reilly) who hit the Vegas strip.

Casino (1995)
Most gambling movies can be classified as thrillers or noirs, but Casino is an epic, telling the sprawling history of the mob’s involvement in Las Vegas. It also ranks just behind Goodfellas on our list of “Martin Scorsese movies where Joe Pesci freaks out at someone” list.

Uncut Gems (2019)
If you’ve ever had even a small amount of money bet on the outcome of a sports match, watching Adam Sandler risk his life based on the outcome of a Lakers game in Uncut Gems is likely to put you into cardiac arrest.

Molly’s Game (2017)
Save for the implication that Molly Bloom (Jessica Chastain) is only successful because she’s searching for the approval of her father (Kevin Costner), Molly’s Game is a damn entertaining look at what it’s like wrangling eccentric gamblers together for high profile poker tournaments.

Tombstone (1993)
It’s a testament to the great filmmaking that watching Wyatt Earp (Kurt Russell) confront an obnoxious troublemaker (Billy Bob Thorton) is just as exciting as any of the gunfights in Tombstone.

Rain Man (1988)
The depiction of neurological disorders may not have aged great, but Rain Man’s story of two lost brothers united by card counting still has a lot of feel-good charms, particularly with Tom Cruise and Dustin Hoffman at the height of their powers. Rain Man was the top-grossing film of 1988 (a year that also included Die Hard, Coming to America, Who Framed Roger Rabbit and Young Guns) — remember when audiences paid to see movies that weren’t about superheroes and lightsabers?

Ocean’s Thirteen (2007)
While not quite as good as 2001’s Ocean’s Eleven, the line “I don’t gamble, not with people’s lives,” is the best of the entire trilogy.

Mississippi Grind (2015)
Here’s a recent under-the-radar film with the potential to be a cult classic. Inspired by the movie star two-hander of California Split, Mississippi Grind follows an unlikely alliance between a serial gambler (Ben Mendelsohn) and a charming card shark (Ryan Reynolds) as they bet on every card game and sporting event in their path.