Most Memorable Gamblers in Film

Film characters that stick with us the most tend to be larger-than-life. That’s exactly what sets them apart from real people. The willingness to throw off the shackles of everyday life and live or die by the luck of the draw.

Now, playing online blackjack with friends is one thing, and it can be an exhilarating experience. But to make a proper gambling film plotline, you need a great character. Someone with more money, bravado, and grit than the rest of us could ever hope to bear. Let’s look at some of the best movie gamblers in history. 

Micky Rosa from 21 (2008)

Every great tale has a speck of truth in it. This truth can be especially fun when we’re talking about using card counting to beat casinos at blackjack. The story of the MIT Blackjack team is one every gambler should know by now, and it inspired this great movie and this amazing character. Played by Kevin Spacey, Rosa is a composite character based on several real-world blackjack pros.

Initially, Rosa is not just a brilliant mathematician with a penchant for games of luck. He’s an all-around hustler, who knows people even better than math. And, as any poker player worth their salt will tell you, gambling is more about people than cards. Rosa uses this knowledge to exploit brilliant young students with promises of riches and paid-off tuitions.

Initially framed as a roguish math teacher, we quickly learn that Rosa is obsessively greedy and quite unscrupulous.  We’ll stop here to avoid spoilers but, needless to say, he’s the most memorable character in a movie full of brilliant performances. 

Bret Maverick from Maverick (1994)

Speaking of poker and lovable rogues, Mel Gibson’s Maverick is one of those names that have become inseparable from poker. Maverick is a bit of a template many gambling movies have used since. He’s a suave traveling swindler and conman, true. But he also has his sights set on more than just cash. He wants to prove that he’s the best at what he does against the world’s biggest poker players. And he’s playing at a disadvantage, too.

Set in the fan-favorite backdrop of the American wild west, Maverick is hardly an original concept. Grizzled cowboys, loaded revolvers, and Texas Hold’em are a tried-and-true combination. However, top movies about gambling such as this take such tropes and make them truly shine. As such, Maverick is a fun trope that went on to influence film more than you’d expect.

Sam "Ace" Rothstein from Casino (1995)

Scorsese is a true master at creating fast-talking, quick-thinking hustlers. In the case of this professional sports bettor and casino executive, though, he didn’t have to create too much. Robert DeNiro’s Ace was based on Lefty Rosenthal, whose real-life story hits a lot of the same beats.

We all know those introductions Scorsese uses to set up larger-than-life characters from the underground. And Ace is the only person ever described as having Las Vegas “clocked.” His wagers are enough to make bookies from across the country change their odds. Ace’s skills are such that the Mob hands him a casino on a silver platter – and he doubles the profits.

Paired with DeNiro’s famous skill at portraying such characters, few gamblers in movies stick with you as much as Ace. 

Raymond “Rain Man” Babbitt from Rain Man (1988)

We’ve already mentioned that these characters can be a bit cliche. Some of them, however, are responsible for creating those cliches in the first place. The (in)famous Rain Man is sometimes blamed for creating an unfair connection between people on the autism spectrum and blackjack card counting. However, that merely speaks to just how impressive Dustin Hoffman’s character is. The footprint the Rain Man left on pop culture is immense.

Raymond is a savant with a perfect, photographic memory. In one of the film’s most entertaining scenes, the eponymous Rain Man uses his talents to fleece a casino blackjack table. Though not a gambling movie per se, Rain Man’s gambling scenes are some of the most influential in movie-making history. Also, the fact in portrayed someone like Raymond as the hero was quite refreshing back in 1988.

Teddy KGB from Rounders (1998)

Rounders is a bit of a cult classic among poker fans, gaining notoriety during the poker boom of the early 2000s. It has everything a great movie needs – a star-studded cast, a gripping high-stakes story, and, of course, an amazing villain. In this case, that’s Teddy KGB.

John Malkovich's performance easily outshines those of his co-stars, and we’re not saying that to degrade anyone. It’s hard to put your finger on why, though. Maybe it’s the campy Russian accent, maybe it’s the strange mannerisms. However, what truly sets the character apart is the adherence to a sort of personal code. Teddy’s personal brand of justice is cruel and remorseless, but one can’t help but see it as just that – justice. This point about him being an honorable villain is hammered home at the end of the movie. He keeps his word and pays his debts – unlike the film’s protagonists, if we may add.

That rounds out our list of the best gamblers in movies. Or at least the most memorable ones. As it turns out, the best gambler characters tend to be villains. Perhaps there’s a lesson in there somewhere, but let’s just end with a warm recommendation for all the movies we mentioned above.