Gritty and brutal tale of the world of high-stakes pool hustling
Watch it: Not available on Prime or Netflix. DVD £2.79 from Amazon.
This is less a tale of pool and more a tale of how we deal with losses, both financial and personal. If that all sounds a bit deep then it also features some of the best pool scenes recorded on film, some top quality betting action and an effortlessly cool performance from Paul Newman in the lead role. The tale of small-time pool hustler Eddie taking on the big time is one any gambler can empathise with and it features the same mix of hope, hubris, heroics and heartbreak we’ve all experienced.
At its heart it’s a film about being human and how we deal with success and failure and what those two things do to our soul and to our wallet. No spoilers, as it’s a cracking tale, but if you come of out this the other side without asking yourself a couple of questions you’re a better gambler than most.
Tip: If you can’t handle losing don’t chase the wins.
The definitive poker film that will have you rushing to the tables afterwards
Watch it: Streaming on Netflix
This is every poker player’s favourite film and one most can quote from endlessly. The story of law student Mike who, surprise surprise, is a bit of a gambling addict and loses all his cash and his journey of revenge and redemption against the man who sent him broke. It sounds rubbish right? So why does everyone love it? The characters are great, especially the just about believable villain Teddy KGB, and the poker is the right side of plausible while also being ridiculous enough to be entertaining.
The poker is treated with real love and there is even some genuine discussion on pre-internet poker theory, while there are some truly iconic scenes including one involving an Oreo cookie and a bizarre tell. Give it a spin and try and resist opening up an online poker table immediately after it finishes.
Tip: Poker is a long-term game. Just make sure your big wins make up for your big losses.
Timeless, funny and ridiculously entertaining tale of an old-school horse racing scam
Watch it: Not available on Prime or Netflix. DVD £4.99 from Amazon.
Arguably the best film on the list, this is a clever piece of filmmaking that somehow makes a massive horse racing con not only believable but edge of the seat exciting. It’s really a tale of the two main characters and their attempts to get revenge on a slightly cartoon-like villain but it’s a hugely entertaining ride and the old-school horse racing world has a wonderfully nostalgic feel to it.
It takes you back to a time when having an edge was as much about getting information before anyone else had access to it as it was analysing and interpreting it. And when you find an edge you exploit the s*** out of it.
But aside from anything else it’s just hands-down one of the all-time great films with two of the all-time great actors in lead roles. Sit back, enjoy and rue how the internet ruined cheating for everyone.
Tip: Learn to cheat. Find your edge and milk it for all its worth.
Win it All
Modern comedy drama morality tale of a poker player who gets in way over his head
Watch it: Streaming on Netflix
Most gambling movies contain the same cliches about a hopelessly addicted degenerate, usually battling some kind of deep personal issues, who despite looking like he is about to drag himself out of the mess with one final shot at glory somehow manages to f*** it all up. At first glance this appears to be another one to chuck on the pile, but it’s a lot smarter and more subtle than that.
Essentially it’s a story of a guy who is down on his luck and finds a bag of money and proceeds to rinse through it at a rate of knots before trying to “win it all” back. Can he do it? What do you think? Smartly written and with characters that go beyond your usual poker player on a downswing trope make this a good watch with an ending that will likely live in the memory.
Tip: Erm. Don’t be a gambling addict? More seriously bankroll management is all.
Two for the money
Stupid but surprisingly entertaining film about Sports Tipping
Watch it: Watch it: Not available on Prime or Netflix. DVD £3.19 from Amazon.
Another absolutely top-quality cast with Al Pacino, Matthew McConaughey and Rene Russo coming together for the unexpectedly dramatic story of a sports-star turned handicapper (McConaughey) and his gradually building war with rival tipster and mentor Pacino. Handicapping is a serious business in Vegas and the high-stakes nature of the world may surprise some but the themes will be achingly familiar to anyone who’s placed a sports bet before.
The shady world of professional tipsters is pretty well laid bare here, but it also conveys the tension, adrenaline rush and mentally bruising nature of sports betting with real heart. There is, of course, the obligatory love story sub-plot and it loses its way a bit towards the end but it’s well worth two hours of your time.
Tip: Never pay money for tipsters unless you are 100% sure of their record
The Legend of Jimmy the Greek
Larger than life tale of one of Vegas’ most legendary sports bettors
Watch it: Hard to find on DVD, easy to find on YouTube
As part of the slick 30 for 30 ESPN documentary series this episode focuses on pro-bettor and one-time TV commentator James Snyder who was better known as Jimmy The Greek. After arriving in Vegas in the mid-50s he set up one of the first sports tipping lines on the then nascent NFL, which eventually led to him appearing on CBS to make predictions on upcoming games. His oblique references to gambling and the use of point spread style predictions helped popularise sports betting on the sport and he’s widely considered one of the bigger influences on helping make betting on the NFL one of America’s most loved pastimes, even if it’s technically illegal in most of the country.
But it’s not a story that ends well for Jimmy and this fascinating documentary shows how far he rose and how fast he fell. It’s well worth seeking it out on YouTube, if nothing else to finally understand a stream of TV and film references you never really understood before.
Tip: No matter how good you are at betting, don’t be an a***hole
Sports data geeks are the heroes in this unlikely blockbuster about baseball and data-mining
In the purest sense this isn’t a gambling film at all, but it contains more lessons about how to win at sports betting than all all the other films on this list combined. Moneyball is the mostly-true tale of the Oakland A’s rise from zeroes to heroes in Major League Baseball in the US thanks to a radical shift in how they recruited their players. It’s a pretty traditional narrative with two down on their luck heroes in the shape of the A’s general manager played by Brad Pitt and his newly recruited stats-geek played by Jonah Hill adopting a radically new approach complete with a false start before they hit the bigtime.
What the A’s do in the film, and actually did, was find a way to win by analysing the data that mattered and ignoring the noise. If there is a better lesson to winning at sports betting we’d love to know what it is.
Tip: This is how you win at gambling folks. It’s not about gut feeling, it’s about data.
Let it Ride
Genuinely funny hidden gem about horse racing betting
Watch it: Hard to find, but stream or buy on Amazon Video for £3.49
Have you ever had one of those days at the race course where you can’t stop winning? That’s the theme of this late 80s comedy gem where Richard Dreyfus plays the cliched down-at-heel horse racing degenerate who hits on a ridiculous winning streak and keep upping and upping the stakes until he’s placing a life-changing bet on the last.
Yes of course it’s a bit ridiculous, but everyone who’s spent time betting on horses has had moments that feel a bit like this and while it’s an American track the environment will feel weirdly familiar to any British racing fans and there are lots of genuine laughs to be had from the script and cast. With music by Giorgio Moroder and that man Dreyfus in a lead role it’s a real blast from the past, but still stands up to repeated viewing today.
Tip: When you’re on a hot streak, push. But don’t push too hard.
Solid documentary on the legendary MIT card-counting blackjack team
Watch it: Easy to find on YouTube
If you’ve not read the book by Ben Mezrich then this US made-for-TV dramatised documentary will be a fascinating watch. It’s the story of a team of students from a US university who perfected a card-counting system that they used to take Vegas casinos for huge sums of cash. The combination of mathematical strategy and old-fashioned con trickery required to pull this off makes this a massively entertaining watch, if you can forgive the slightly cheesy American production values.
Blackjack remains one of the few “skill” games at the casino and one where given the right conditions and the ability to fly under the radar of the watching staff a skilled team can still beat the house. But as you will find out from the film this doesn’t come without some serious consequences. The house, it seems, always finds a way to win in the end.
Tip: Learn how to count cards and how to run fast
Hard edged and realistic story of poker pros fighting their demons on the road
Watch it: Streaming on Netflix
At first glance this looks like another godawful Lucky You style look at the world of professional poker with pretty boy Ryan Reynolds in the lead role and a generic “mid-life crisis” gambler on a downward spiral as his buddy for the road trip. But this is a smartly written and acted film that doesn’t go for lazy cliches and takes it time to let the story and characters build.
The poker is almost an aside to what is more of a meditation on the role of luck in life and what gambling for a living can do to a man’s soul.
If you want a light-hearted knockabout with a guys getting dealt quads over quads this isn’t the film for you, but if you want a film about gambling warts and all then check it out.
Tip: Don’t underestimate the role of luck in everyone’s life
Holy Rollers: The True Story of Card Counting Christians
An unlikely tale of a hugely successful Christian pro-blackjack team
Watch it: Pretty easy to find on YouTube
This isn’t a clever title or a parody, it does what it says on the tin here. This is a documentary about one of America’s most successful professional blackjack teams and how they came together and learned to count cards and beat the casinos time and time again.
The film tries to balance the role of religion and gambling in the team’s lives but mainly just uses interviews and clips to tell what is a pretty extraordinary tale of pretty normal people smashing up Vegas for $$$$. It’s fascinating to see how involved the scheme is and how complex and serious a business card counting can be and the filmmakers do a great job of keeping the pace up and letting the story unfold.
Tip: Gambling isn’t bad if you do it properly
Paul Thomas Anderson directs a stellar cast in a lost classic
Watch it: Streaming on Netflix
Celebrated director Paul Thomas Anderson’s first film was a low-budget gambling flick with a cast including the always brilliant Philip Seymour Hoffman and Gwyneth Paltrow but it’s Philip Baker Hall in the lead role who steals the show. Professional gambler Sydney, played by Baker Hall, is who this film revolves around and it’s a plot that gently unfolds through a mix of beautifully judged dialogue and Thomas Anderson’s now trademark directorial style with sweeping tracking shots all over the shop.
Gambling is the setting rather than the content of this story and it’s all the better for it with the casino giving the film its heart and its edge while the engaging story of those who try and make money from it plays out. Definitely worth a couple of hours of your time.
Tip: Sometimes you just have to deal with what life throws at you
The Cincinnatti Kid
Last but by no means least The Cincinnatti Kid is a must watch.
Watch it: Available to rent on Amazon.
It’s probably been a few years since I’ve seen The Cincinnati Kid, a while since I’ve seen it for maybe the fiftieth time. But it’s a still a movie that I can guarantee you I would never ever go past if skipping channels and lucking into a classic rerun on TMC, as I’ve done many times. It is too great a gambling film, through and through.
Let’s talk about the players. The classic hero arc without a shred of sentiment. There’s the Kid, all the talent in the world and trying to be the best that ever was. There’s the Man, unloved and unfriended and maybe past his prime, who knows that it always comes to character in the end. There’s the Shooter, wise and bitter and failed, who still remembers that he was once a Kid himself.
There’s every gambler we’ve ever known.
Like the hard luck Pig who must always go broke, or the Doc who still believes a system can win, or Yeller who has a joke for every hand. There’s the millionaire Slade who just wants to win so he can dance on a grave and doesn’t care how it’s done. And Ladyfingers, of course, who has seen it all so many times that the story has played out before it even begins.
People like to point to the hand dealt in the scene near the end as too against the odds to be true, but everything else in this movie when it comes to gambling is spot-on. Every gambler that I’ve ever known can find their story in here, perfectly expressed.
Has a better New Orleans Film ever been made? That rough and beautiful city, complete with funeral jazz processions, gold teeth ladies banging the blues, and the poker games out behind the railroad tracks or in a back bar or the catered suite of a fancy hotel.
The Cincinnati Kid is a gambling story in all it’s glory and I won’t even tell you who wins. But that’s something that you should already know.
Tip: Drop what you are doing and watch this.