Whether or not you participate in it yourself, it’s hard to deny that on occasion online gambling can be fun. Betting on a horse race or maybe playing a hand of blackjack gives you a pretty tremendous rush of adrenaline, and this is especially true when you actually win. Of course at the same time, online gambling can be a pretty horrendous affliction, one that can ruin lives and lead to bleak outcomes for the people doing the betting.
Fortunately for us, Hollywood is around to give us views of gambling from every side, and it’s only just mostly skewed toward whatever message the studio is trying to send. Obviously some films glorify gambling, while others treat it as the most dreaded disease known to man. So naturally, we can safely say gambling tends to fall a little closer to the middle of that particular spectrum. The exaggeration for the sake of film, though? Heck, most of the time that just enhances the pleasure of watching those movies, such as…
People sometimes forget that, before he went insane and became an over the top racist, Mel Gibson made some pretty enjoyable movies. One of those films was Maverick, which kind of gets forgotten about these days but remains one of the better television show adaptations in Hollywood history. And the entire movie revolves around gambling, gamblers, and one massive poker tournament on a riverboat that the titular hero is trying to get to in hopes of winning half a million bucks, which as you might guess, is a good amount of cash in the Old West.
The script was written by William Goldman, and the movie features strong, likable performances from Gibson, Jodie Foster, and James Garner (who starred in the original television series), and there’s clearly enough gambling going on throughout the film to qualify for this list. There are obviously other plot points that maybe hold more significance throughout the movie, but the build up to the big card game and the actual, climactic montage right up to the final hand is well shot and a lot more thrilling than a simple card game has any right to be.
9. Silver Linings Playbook
For as critically acclaimed as Silver Linings Playbook was, it sure does seem like there are a lot of people who not only have never watched it, but also have basically zero clue as to what it’s about. About all they know is that it stars Bradley Cooper, Jennifer Lawrence, and Robert De Niro, and somehow relates to the Philadelphia Eagles and perhaps some dancing. Directed by David O. Russell, the movie actually deals not only with mental health issues, but also gambling addictions.
See, in the film, De Niro’s character – the father of Cooper’s character – has a pretty bad gambling addiction. He likes to bet on the Eagles, and as any Philly fan will happily tell you, that’s a horrible idea most of the time. Somehow, this leads to De Niro making a parlay bet that includes not just the Eagles, but also Cooper and Lawrence’s finish in a dancing competition they’ve entered. Because apparently bookies take bets on literally anything these days.
It’s a shame that more people don’t remember Diggstown and speak of it in reverential tones, since it featured a stellar cast and should be ranked as one of the best, and arguably most fun boxing movies of all-time. To set up the premise for you, James Woods plays a con-man who is just out of prison, and he’s headed to Diggstown, named after a retired boxer who was poisoned in his last match. Woods uses his old pal, a washed up boxer played by Lou Gossett, to set up a bet saying that Gossett can knock out any 10 fighters the town can dig up in a 24 hour period.
The movie is funny, and surprisingly dark, and features some solid fight scenes along with some twists and turns as Woods and the crooked figure at the center of the town, played by Bruce Dern, try to get the best of one another all over the course of one 24 hour period, for the sake of this one, massive bet. Some of the other people who pop up in supporting roles are Oliver Platt, who is as awesome as always, and a young Heather Graham, who still couldn’t act even back in the Diggstown days. But at least she was cute, right?
While not a standard gambling movie per se, as the main plot doesn’t revolve around a single horse race, card game, or other such game of chance, it’s hard to imagine a list about the best gambling movies ever that doesn’t include Casino. This was an unofficial follow-up to Goodfellas, with most of the key players returning including director Martin Scorsese along with stars Robert De Niro and Joe Pesci.
Considering the movie takes place almost entirely around the rises and pitfalls of running a casino, clearly gambling is at the forefront even if it’s not the key piston in driving the plot forward. Just like with Goodfellas, Casino was based on real life people and situations, though obviously some liberties are taken in the story of sports handicapper “Ace” Rothstein, played here by De Niro. The movie is all about how intertwined the worlds of gambling and organized crime are, though let’s be honest here, that’s not exactly a big surprise to anyone who’s ever read a single article or seen one movie about betting, and loan sharks, and vigs.
Probably the most obscure film on this list, Croupier is the movie that really introduced Clive Owen to the world. It was after this movie that people wanted to see him don the tuxedo as James Bond, though obviously that didn’t wind up happening. But we’ll get back to 007 in a minute. If you are unaware, a croupier is the guy who runs a gambling table at a casino, whether that means he’s the blackjack dealer, or runs the craps table, or what have you. In the film, Owen plays an aspiring writer turned croupier in a story that’s got a bit of a noir feel.
The film deals with Owen’s character becoming more and more involved with the seedier sides of the casino business, including hanging around with fellow croupiers who are secretly stealing from the casino, and eventually he winds up serving as the inside man for a casino robbery. One thing leads to another, a few twists are revealed, and at the end of the film Owen is still working as a croupier despite full knowledge that he was pretty much manipulated by an outside source from the start. Oh wait, should we have said spoiler alert? Well, too late now.
5. Casino Royale
Well, we mentioned Bond, James Bond in the last entry, and we couldn’t well leave you hanging for too long. Casino Royale has actually been done multiple times, but we’re sticking with the most recent version starring Daniel Craig in his first appearance as everyone’s favorite MI6 agent. It’s not often that you can make a movie about the world’s greatest secret agent playing Texas Hold’em, but that’s exactly what happened with this film. And critics and fans alike agreed that it was one of the greatest Bond films ever made.
The fact that a Bond movie about gambling can legitimately be ranked alongside something like Goldeneye is a pretty strong statement, but it’s deserved. The film centers on Bond entering an incredibly high stakes poker tournament run by international terrorist Le Chiffre, and a good chunk of the action takes place in and around the card game as tensions rise on all sides. In fact, Casino Royale is so good at portraying Bond in a relatively mundane setting like a card game that it almost makes you wish future 007 films would get smaller in focus as well.
4. Eight Men Out
There may not be a more famous sports related gambling story than that of the 1919 Chicago White Sox, the team that had eight members take bribes to throw the World Series. All eight men, including Shoeless Joe Jackson, were banned from baseball for life once their misdeeds were brought to light, and the movie is incredibly compelling despite anyone who’s ever paid any attention to baseball history knowing full well where it was going to wind up.
Eight Men Out has a fantastic cast that includes the likes of David Strathairn, John Cusack, Michael Rooker, John Mahoney, Charlie Sheen, and Christopher Lloyd, and was written and directed by two-time Oscar nominee John Sayles. The story of how the eight ballplayers were convinced to not only take part in this scam but remain deeply entrenched despite their own misgivings is tremendously well told, and the product is not just one of the greatest baseball movies ever made, but also arguably the best sports betting movie as well.
Between Croupier and Rounders, 1998 was a big year for gambling movies. Rounders of course wound up being the higher profile film, as it starred Matt Damon and Edward Norton, two guys who were both sizzling hot in Hollywood at the time. There haven’t been many movies that have been more unabashedly about gambling and playing cards than Rounders, particularly considering the title itself refers to a card player who bounces around from city to city looking for high stakes games to get in on.
Sure, there are some pretty laughable parts of the movie, most notably Gretchen Mol’s performance and John Malkovich’s unintentionally hilarious and over the top Russian accent, but in terms of pure poker, you’d be hard pressed to find a better movie save for perhaps The Cincinnati Kid. Rounders tells the story of a kid with a bright future, but a knack for playing poker, who starts to fall into the seedy world of underground gambling, and it does so with such success that people have been wondering for years whether we’ll ever see a sequel.
2. The Hustler
Of course not all gambling movies revolve around playing cards. Most of them do because a card game is relatively cinematic and it’s easy to build the tension during a big hand, but there are some films, like The Hustler, that involve different forms of gambling. In this case, the 1961 film – which eventually received a sequel starring Tom Cruise called The Color of Money – is about pool hall hustlers, and starred a young Paul Newman alongside Jackie Gleason as the now iconic character, Minnesota Fats.
The movie tells the story of a young hustler named Fast Eddie who wants to become a big time billiards shark, eventually taking on the legendary Minnesota Fats and, in their first meeting, losing to the more seasoned pool player. The movie takes some dark turns, and while Fast Eddie eventually gets the best of Minnesota Fats, it’s made clear that his success has been achieved at a tremendous cost. The movie earned two Oscars and was nominated for seven more so, yeah, it’s just a little bit good.
1. The Sting
Yes, this means we’re saying that Paul Newman pretty much cornered the market on amazing movies about gambling, particularly when you factor in The Color of Money. Coincidentally, his Hustler co-star Jackie Gleason starred in the pretty awful sequel to The Sting. Anyway, if you’ve never watched The Sting, do yourself a favor and check it out as soon as possible. Starring Newman, Robert Redford, and Robert Shaw, it’s a fantastic story about con-men, gamblers, and thieves in Chicago around the time of the Great Depression.
Basically, the story revolves around Redford and a friend hustling one of Shaw’s couriers, and after Shaw, a big player in the world of organized crime and gambling, gets some retribution by killing Redford’s partner, he seeks out Newman to concoct an elaborate betting scam to take Shaw for just about everything he’s got. The grift at the center of the story is ingenious, and the dialogue and performances turn this into an absolutely transcendent film that was nominated for 10 Oscars and won seven, including Best Picture at the 1974 Academy Awards.