Best Gambling Films: Ranking the top 10 ever made

Stryker Maguire loves everything about betting, so when OddsCritic asked him to rank the best gambling films ever made, he reacted by doing cartwheels in his Tennesee trailer.

Once he recovered from the resulting quad injury, your faithful correspondent opened his laptop and pondered on a life in gambling, and the landmark moments on his betting journey.

Some of those moments involved watching gambling epics on the big screen. Some of those moments shaped the man he is today. When he isn’t picking the winner of fights or betting on NFL games on fall Sundays, he’s watching stuff like this.

How we ranked our top 10 gambling films

Stryker is making one thing clear right now – he isn’t looking for a writing gig on any movie magazines. He’s not some academic with glasses forever perched on the end of his nose while he strokes his chin/s.

This list is based on sheer brilliance – Stryker is a maverick and our top 10 is ranked for the best of reasons – how did these epics make him feel?

So, here we go…

10. The Hangover (2009)

When Stryker was a younger man, he loved a weekend in Vegas. Heck, it was a prerequisite if you wanted to gamble properly before betting laws changed. Stryker is always all in on doing things properly.

He had many weekends similar to the bachelor party trip enjoyed by Bradley Cooper, Ed Helms, Zach Galifianakis and Justin Bartha. The only thing he hasn’t done is gotten decked by Mike Tyson for stealing a tiger. Oh, and he never married a stripper (at least he can’t remember it).

The mix of characters is perfection and the storyline is hilarious – Stryker suggests watching with a half dozen cold ones in the ice bucket and a 16” pizza on deck. Pure gambling heaven.

9. ’21’ (2008)

While The Hangover included the sort of weekend Stryker did indulge in during his formative years, ’21’ included the type of getaway he aspired to but never experienced.

You see, your faithful reporter didn’t make it to college – he learned about writing from reading Sports Illustrated in the restroom of a honky-tonk in Nashville. Why it was there every week? One of the stranger things in life.

Anyways, Stryker would have loved his high-school teacher to take him to Vegas every weekend after teaching him to count cards (just not Kevin Spacey, thank you). Instead, he just constantly predicted a prison life for Maguire. How wrong he was.

’21’ is exactly the sort of film kids should watch when they are told to think big. It’s also a lesson in life – when you look up to people, they invariably end up disappointing you at some stage down the line.

8. Ocean’s Eleven (2001)

One thing Stryker does admire is style. And it comes out of every pore in George Clooney in this modern classic. Great cast and a fun storyline – if a little far-fetched. But not nearly as far-fetched as Don Cheadle’s lamentable London Cockney accent. Stryker has friends (gambling friends obviously) in the UK capital, and your man Don is straight embarrassing here.

Stryker though can see past the odd bad point – Cheadle at least provided a little comedy to add to the fast-moving script and wise cracks.

Don’t expect award-winning drama and tension here, this is fun and style with a dose of Vegas wildness. Nothing better.

Oh, and btw, as a boxing betting aficionado, Stryker loved to see Lennox Lewis and Wladimir Klitshko getting it on at last. A fight that never happened in real life. See, gambling can even fix the filthy fight game.

7. Last Vegas (2013)

Stryker just realised there’s a strong thread developing in this top 10 – they’re mostly about stuff he’d like to do. At this stage Maguire has never married a woman half his age (yet) – but that doesn’t mean it’s something that is totally off his radar.

This terrific film also features the genius that is Robert De Niro. Stryker has yet to watch an RDN film he didn’t like – and yep, you can include ‘Dirty Grandpa’ on that list.

Anyways, our stellar cast lands in Vegas (always) for another bachelor party, and after a great start things start to go south.

Talking of marrying a woman half your age, funny how Michael Douglas actually did it real life too. Hollywood rules.

6. Atlantic City (1980)

By the time he got to #7 on this list, Stryker realised he had a little too much Vegas running through it. Step forward Atlantic City.

The weather may not be as nice in New Jersey as it is in Nevada most of the year round, but AC is a treat that anybody should experience at least once in a lifetime. It’s also probably the best place to bet since online bookmakers set up shop in 2018.

Anyways, Sally (Susan Sarandon) plays a croupier in an Atlantic Casino who ends up romantically involved with Lou (Burt Lancaster). Lou is really just a petty thief but he thinks he’s a huge deal – a real big hitter.

The only problem is, Lou pretty soon ends up having to back up that reputation when a drug deal goes south. Stryker likes him some Burt – and some Sarandon. He even shed a tear or two. Great film and essential for any gamblers out there.

5. California Split (1974)

There are a ton of gambling film gurus out there who likely have this epic at #1 and Stryker has no issue with that – each to their own.

Elliott Gould already featured elsewhere on this list in Ocean’s Eleven, but that is second best compared to his sensational performance in this betting classic.

Gould takes fellow gambler George Segal on journey to the darker side of the game – George is a magazine guy who likes gambling but isn’t in quite as deep yet. That changes pretty fast.

Stryker did think just for a second this was the first movie on the list that didn’t feature something he wanted. Then he remembered the wisecracking Gould is the big brother he never had.

4. The Sting (1973)

Another classic gambling movie – and this time about something Stryker has never wanted to do. Namely con a mob boss.

Maguire has no desire just yet to swim with the fishes, but he did admire professional grifters Robert Redford and Paul Newman for their masterplan to pull the hood over Robert Shaw’s eyes.

As well as being a classic involving one of film’s great double acts, it does eventually include something Stryker has always thought would be a career achievement. Sleeping with a paid killer and living to tell the tale.

The soundtrack for the move is also a beauty – it’s a little known fact that Stryker taught himself to play piano at age 23. The first tune he learned = ‘The Entertainer’. You’re welcome…

3. The Hustler (1961)

Newman is another of Stryker’s favorite all-time actors – apart from a brief period when he went out with a waitress who was obsessed with the Hollywood idol. Yeah yeah, I know he he has blue eyes…

Anyways, Newman plays a stellar role as pool hustler “Fast” Eddie Felson, who has to rebuild his life and his confidence after a shattering loss to pool legend “Minnesota Fats”. Their marathon showdown is epic, and worth watching for the final moments alone. Stryker even teared up again.

Eventually Eddie has to choose between his soul and his girlfriend, and reaching the top. Which way will he go?

2. The Gambler (1974)

One thing to make clear right away – we’re talking about the 1974 epic not the 2014 version of the same name starring Mark Wahlberg and Brie Larson. Stryker is partial to a little Wahlberg (Boogie Nights is right up there) but you can’t remake a classic.

James Caan is stellar as New York-based English professor Axel Freed who is in deep. A gambler with a problem and a debt to match. That’s where Paul Sorvino comes in as his bookie Hips. We love Sorvino – terrific in Goodfellas, another film which rates highly on Stryker’s all-time list.

The only way out of the debt for Axel is to get one of students – a basketball star – to help fix a game. From there the film spirals into the darkest of places. Gripping and must-watch for anybody who ponders the gambing psyche.

1. Casino (1995)

Ok folks, one thing Stryker should disclose right off the bat here – he loves De Niro and Pesci. And I mean loves them.

Heck if he could die, go to heaven and come back as a movie bad guy, Pesci would be his guy.

The plot and MO from Martin Scorsese is nothing new here. Let Joe generally cause mayhem, and have RDN pick up the pieces. It happens on a grand scale here.

As with all films, there’s a twist in the tale – in this instance it’s gruesome and Stryker likes nothing better.

The site of Pesci in his underwear getting his just desserts – via a baseball bat in the desert – warmed your writer’s heart like nothing else. He loves De Niro too (may have already mentioned it), and this time Bobby was the good guy. Proof that sometimes, good guys can win.