The Ten Best Gambling and Poker Films

Paul Schrader’s The Card Counter came out earlier this year, which prompted me to reflect on one of my favourite sub-genres of film: the gambling flick. They are an obsession of mine, in part, because so many of these movies are also noir. That, and my being a semi-professional poker player for several years.

Thus the list that follows is derived from some semblance of credibility. I was never a degenerate gambler (of the many flaws I have, this is not one of them), but I was a serious poker player. ‘Semi-professional’ is a way of saying I depended on part of my income from playing cards. I always won, year in and year out, and so could rely on that money

The world of gambling – the degenerates, the thrill seekers, the idle rich burning money, the desperate poor chasing losses, the recreational gamblers, the young geniuses, the old sharks – is, if nothing else, far more interesting than the rather staid, upper-class world of publishing.

The list only includes films where gambling is central to the plot and the protagonist. Thus, for example, Casino isn’t on this list, because (despite its name) it is a gangster film rather than a gambling film. Casino Royale, which (again, despite the name) is a very good Bond film, but a downright terrible gambling film. It ends with one of the most hilariously improbable poker hands of all time (nut flush v full house v  higher full house v straight flush), and precisely the kind of hand written by someone who neither plays nor understands the game.

Enough preamble, the list*:

=10) California Split (1974)

The Robert Altman technique of letting actors blather on – with unscripted dialogue, speaking over the top of each other – may be celebrated among auteurs, but is fucking annoying for regular viewers. Putting aside this tendentious film-making technique – so-called naturalism – California Split is an okay buddy film about the degenerate duo of Billet Denny (George Segal), and slow-rolling dickhead Charlie Waters (Elliott Gould). It does a decent job of showing the obsessive, thrill-seeking side of the problem gambler.

=10) Molly’s Game (2017)

I hesitate to include this film, not because it isn’t any good (it’s certainly better than California Split), but because the protagonist is not a gambler, and her only addiction is drugs. She (the titular Molly, played by Jessica Chastain), runs a private poker game for celebrities and wealthy socialites. It is, apparently, based on a true story (written by the real-life Molly Bloom), and revolves largely around ‘player x’, a celebrity who helped create the game, and attract many of the participants. Player x (played by Michael Cera) comes across as as spiteful and selfish, and is supposedly based on Tobey Maguire. Whether or not Molly Bloom told the whole truth in her memoir (apparently she did not), she was almost certainly telling the truth about that well-known tool and sub-standard Spiderman, Maguire. 

9. Hard Eight (1996)

The only enduring memory I have of this film is when Sydney (Philip Baker Hall, who I always think of as the library cop in Seinfeld) begs Jimmy (Samuel L Jackson), not to kill him. (Spoiler alert – this is a pretty good movie, so if you haven’t seen it, stop reading now). Jimmy lets him live, but demands money from him. Later, Sydney breaks into Jimmy’s house, waits patiently, and then shoots that bad motherfucker when he returns home.

It’s a good film about gambling culture, and the nature of gamblers, by a good director (Paul Thomas Anderson, in his debut). It co-stars Gwyneth Paltrow, back when she still appeared in Indi films and before she started selling vagina candles to credulous morons with too much disposable income to their names. Philip Seymour Hoffman also plays a small but incandescent role.

8. The Gambler (1974)

James Caan plays professor of literature and gambler Axel Freed. The academic aspect gives him the opportunity to quote and discuss Dostoyevsky during conversations with his students, and boy do I love some serious literature mixed in with my gambling tales. I love even more the story behind Dostoyevsky’s short novel, “The Gambler.” The great Russian writer was also a degenerate. A genius who yet thought he could beat roulette with a ‘system’, he went stone broke and was in great debt. And so, as a means to pay his debts, he made a desperate wager. If he won? His debts forgiven. If he lost? The publishing rights to all of his past and future works. The wager? Complete a new novel within 30 days.

What a gambler.

While the story of how Dostoyevsky’s novel came to be is more interesting than the one told by the 1974 film, the latter is still pretty good. Caan plays the part well, and wears a set of funky 70s ultra-tight attire that would be the subject of student complaints in the universities of today.  The ending of the film is – wow – dark and brutal, even by today’s standards.

7. The Hustler (1961)

This is as much about alcohol addiction as it is about a gambling addiction. And about hustling as it is about gambling. Like poker, pool is a skill game. Yet the hustle is an art form. Knowing precisely the breaking point of an opponent, knowing how much money you can extract from them. You can hustle by being skilled enough to lose convincingly (and thereby emboldening your opponent to make bigger bets), or simply by increasing the bet size until a superior opponent cracks under the pressure.

The Hustler is far darker than it’s sorta-kinda sequel, the Colour of Money (1986), wherein Fast Eddie (Newman) teaches a brash character Vincent (Tom Cruise) the art of the hustle.

The Fast Eddie of the original has a drinking problem, a temperament problem, and a gambling problem. The movie begins, as many of these do, with his enduring a crippling loss against the legendary pool player ‘Minnesota’ Fats. It charts his path to redemption, but boy, he loses much – perhaps too much – on the journey.

6. The Cincinnati Kid (1965)

Lancey Howard ‘The Man’ (Edward G Robinson), and the Cincinnati Kid (Steve McQueen), face off in one of the ultimate heads-up poker duels of all time. This would have been rated higher, if not for the ending, which we shall get to in a moment. The card games overall are realistic, the actors very good, the dialogue ever-quotable, such as:

Lancey Howard: “It’s a pleasure to meet someone who understands that to the true gambler, money is never an end in itself, it’s simply a tool, as a language is to thought.”

And

Lancey Howard: “All you paid was the looking price. Lessons are extra.”

The ending, however, is ruined by the Casino Royale syndrome, with the Kid on the receiving end of the coldest of cold decks** when his Aces Full go down to The Man’s straight flush. Worse, it tries to paint this final hand as a question of skill, when losing monster over monster is simply a question of dumb fucking luck.

The bullshit nature of the final hand is discussed by Anthony Holden in his book Big Deal: A Year as a Professional Poker Player. He calculates the odds of it happening as more than 332 billion to 1 against, and says: “If these two played 50 hands of stud an hour, eight hours a day, five days a week, the situation would arise about once every 443 years.”

Holden’s book, I should add, is a pretty good example of the tiny sub-sub-genre of ‘writer-tries-gambling’. His book, The Biggest Game in Town (Al Alvarez), For Richer, for Poorer (Victoria Coren), and Positively Fifth Street (James McManus), are the best examples, and the only three worth reading in this area.

** ‘Cold decked’ is a poker term for when two huge hands go up against each other, and nothing can stop all the money going in the middle. The term comes from when a card cheat would replace the deck being used with one they’d set up in advance. The set-up deck was ‘cold’ insofar as the cards hadn’t been handled until that point.

5. The Croupier (1998)

I’m partial, as you may imagine, to movies about writers who are also gamblers. In this, Jack (Clive Owen) is not quite a gambler, rather, he is a croupier addicted to seeing people lose. He’s addicted to the industry itself. After every shift he has the shakes: he’s so amped up after watching the punters lose for hours on end.

He’s also a writer, drawing inspiration from the demimonde he inhabits every shift. There’s a scene where Jack stands on the bus, looking at passengers reading books, daydreaming about the day when he will see someone reading his book. It’s a fantasy I’ve had myself. The problem is that it has become a dead fantasy, or at least one on life support. Passengers don’t read books on public transport anymore, they play candy crush and doom-scroll twitter.

Anyway, while there are a number of anachronisms about the writing life – the relative ease of publishing, the opportunities available to unpublished authors (apparently plentiful), the massive rewards when you do so – it’s still a very good film, mostly well-written, and a deserved inclusion in this list.

4. The Card Counter (2021)

Paul Schrader is a thoughtful, intelligent, compelling, and uncompromising film-maker, in an era of franchise films that are bloated, market-driven, and lowest-common-denominator. He wrote the classic neo-noir Taxi Driver (1976), and his 2017 movie, First Reformed, was the best film of that year.

The Card Counter does not quite reach the heights of First Reformed. This is in part, I think, because the central relationship of the film – between the protagonist William Tell (Oscar Isaac) and a younger man, Cirk (Tye Sheridan) – lacks any real spark, or much in the way of internal logic.

It is, however, still a very good film. It is the only gambling movie I am aware of that accurately portrays the modern poker world. Tournaments, staking, running stables (a wealthy investor backing a group of poker players) and also the grind: the repetitiveness – and emptiness – of the life of a travelling tournament player.

As with many Schrader films, it also explores trauma, psychological distress, and asks hard questions about morality and justice.

3. Uncut Gems (2019)

This is Adam Sandler’s best movie (although Punk Drunk Love is pretty good, as well). Sandler plays Howard Ratner, a jewellery store owner and gambling addict who owes money to a loan shark.

The film evinces that queasy inevitability of the compulsive gambler using, and then alienating, friends and family. Of destroying everything of value in their lives. The viewer sits there thinking it can’t get any worse, but knows deep down it probably will. Hoping that the main character can’t sink any lower, but somehow knowing they yet will. And they do. He does.

Uncut gems is an exhausting yet compelling portrait of addiction.

2. Mississippi Grind (2015)

Gerry (Ben Mendelson) and Curtis (Ryan Reynolds) play an unlikely duo of degenerates, with the former believing the latter is a good luck charm.

This is a modern version of Californian Split, better if for no other reason that the actors have lines and say those lines clearly, rather than the Altman technique of no script and every idiot speaking at once. But there are other reasons: Mendelson is a better actor for one, and for two, it goes to a far darker place.

Mendelson is a great character actor, and I’ve been pleased to see him go on to some level of mainstream success by playing a series of bad guys (Star Wars, Ready Player One etc.). Obviously he is far more interesting to watch in independent films such as this, where he inhabits the role of a melancholic loser who has truly stepped into the abyss of addiction, squandering everything dear to him in the process. The best gambling films, like this one, make the viewer uncomfortable. Moreover, they should make the viewer uncomfortable, given they are examining an industry that is venal, corrupt, and destructive of human life.

Having said that, and without giving anything away, Mississippi Grind is not entirely a miserable affair. You are allowed some hope.

1. Rounders (1998)

This is not the best film on the list, but it is my favourite. There is a generation of poker players (I am one of them) who emerged after Chris Moneymaker won the World Series of Poker in 2003, which went on to discover and fall in love with this cult film. It has an amazing cast: Matt Damon (as Mike), Edward Norton (Worm), John Turturro, Famke Janssen, Martin Landau and John Malkovich. The latter plays a gloriously overblown, scenery-chewing Russian gangster named Teddy KGB (Matt Damon tells a very funny story about the Malkovich performance).  Rounders is the most influential poker movie of all time; even now, 23 years after it was released, it still gets quoted time and again at the poker table.

From the opening line:

Mike McDermott: “Listen, here’s the thing. If you can’t spot the sucker in your first half hour at the table, then you ARE the sucker.”

To one of the great pre-poker trip pep-talks:

Worm: “You know what always cheers me up, when I’m feeling shitty?”

Mike McDermott: [siting in a chair in his apartment, with his head looking down] “No, what’s that?”

Worm: “Rolled up aces over kings. Check-raising stupid tourists and taking huge pots off of them. Playing all-night high-limit Hold’em at the Taj, “where the sand turns to gold.” Stacks and towers of checks I can’t even see over.”

Mike McDermott: [his head looks up] “Fuck it, let’s go.”

To the final line from Teddy (that needs to be watched to be fully appreciated):

Teddy KGB: [Referring to Mike after their final game] “He beat me… Straight up… Pay him… Pay that man his money.”

Rounders has a neo-noir aesthetic that credibly captures the underground poker culture of the end of the last century. The poker hands – remarkably –  are all realistic, unlike just about every other poker movie ever made. The culture and the types of people you meet in Rounders are much like those who inhabit the real poker world (again, except Teddy KGB).

It follows the familiar arc of these movies. A devastating loss followed by a path to redemption. But boy, the journey is brutal, and the culmination – much like The Hustler – exacts a heavy price.

*Only one of these films has a female protagonist. Such films are very rare. While there is an even mix of men and women in the casinos I have been in, women are far fewer at the poker table. At a full table of nine, I’d expect to see no more than one or two. As for the remainder of the casino: problem gambling seems to be a much more common affliction with men, with some studies showing they are seven-and-a-half times more likely than women to develop a serious addiction. Despite all of this, as a writer, this seems to me to be a story space in want of being filled. In addition, only one of these films is from outside the US (The Croupier). While it is true that Australian cinema has very few offerings in this sub-genre – surprising considering our national addiction to the punt – it is also true that I have not actively sought out non-US fare, as is my usual practice. The good thing about being a writer is I can now go watch a bunch of Asian gambling films, and call it ‘research’. 

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