10 Gambling Movies That’ll Make You Hit the Strip. The other day, I was bloviating about something or other… oh, shoot, it’s not out yet. Let’s start over. Come June, I’ll push a post wherein I talk about Bonnie & Clyde, it’ll be a hoot. In said movie tear down I started reminiscing about Bugsy and the gloriousness therein. And it maybe that I have a serious connection between my teen years and the movie Bugsy, but it is one of my all-time favorite films. I then started thinking – huh, I wonder how many other Bugsy-esque, gambling films out there are worth watching? And so I figured, heck… let’s make a list of approved THiNC. Gambling films that are really actually worth watching.
Bugsy
It is sad. It is really really sad. What’s sad, Taylor? It’s sad just how few people have seen this glorious film. I’m not even going to tell you about it, I’m just going to command you to go watch it. INTERNET DENIZEN?!? GO WATCH BUGSY!!! Watch it here on Apple.
Molly’s Game
Aaron Sorkin’s biographical crime drama, 2017’s Molly’s Game details one of the more famous modern stories of real-life intrigue. Following the world-class skier Molly Bloom, this movie details her career-ending injury and her slide into the world of underground poker. Starting with involvement in Los Angeles, and some not-so-subtle references to real celebrity players, Molly’s Game moves onto increasingly higher stakes. Eventually cornered by the Russian Mob and accidentally saved by the FBI, the story ends with Molly protecting her players, resulting in a large fine and community service, but no jail time. Read my write up right here and watch it on Amazon.
The Color of Money
Turning back the clock for this one, 1986’s The Color of Money is a sports drama based on pool-hall hustling and the gambling that was born from it. Following the established Eddie Felson and the upcoming Vincent Lauria, The Color of Money tracks a small group of hustlers as they trick opponents all across the United States. Ending with a cheated bet, the movie was a huge hit at the time, and in no small part helped put Tom Cruise on the map. Been working back through a pile of Cruise’s older movies lately and really enjoyed this walk down memory lane.
Uncut Gems
Adam Sandler is officially back. With his debts mounting and angry collectors closing in, a fast-talking New York City jeweler risks everything in hope of staying afloat and alive. I’ve been trying to get to writing up this really fantastic movie – but for the LIFE OF ME it has alluded me like a cheetah on the plains of Africa. (Wait, WHAT? Can I have a mulligan on that one guys? I mean, I’m bound to screw it up occasionally. Wow, that was bad.) It alludes me as to why I can’t get this written up. But regardless, it’s a fantastic film that you should all check out on Netflix.
Rounders
“Rounders” is possibly the worst movie a gambling addict could possibly watch as John Malkovich’s character gambles away most of his life: Law degree, girlfriend, etc., etc. But as he rounds to the ending of the film he excitedly shakes off his losses and asks for another hand. “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.” Watch it over on Google Play. It holds up surprisingly well.
Tricheurs
Literally the best gambling movie that you – I promise you – have never heard of. It’s a glorious thriller about an individual with a horrible gambling addiction (Jacque Dutronc) so bad, that he honestly doesn’t even care if he wins or loses, just as long as he can keep playing. It gets even worse when he gets drawn into a complicated cheating scheme. Join in on the ride, as these characters ride this ICBM straight into the ground. Rent the DVD on Netflix? Wow.
Win It All
Follow Eddie (Keegan-Michael Key), a super small-time gambling addict as we watch him dig himself into an enormous financial hole. Eddie now needs to start winning to dig himself out of said hole. Win it All is an Netflix exclusive by Joe Swanberg and Jake Johnson. I haven’t enjoyed such a fun depressing movie this much in my life! hahaha. Watch it on Netflix.
The Cooler
The Cooler is a brilliant little indie film about a man, Bernie (played by William H. Macy) with horrible luck, who, despite the odds, finds love with a casino waitress (played by Maria Bello) in the middle of a hopeless situation. Macy and Bello shine in these roles and bring an amazing sense of melancholic grit in world that usually too slick for its own good. Watch it over on Tubi.
Mississippi Grind
Ryan Reynolds. I could stop talking now for most of you. OK, it also includes Anna Boden, Sienna Miller, and Ben Mendelsohn. Mississippi Grind follows problem gamblers Gerry and Curtis as they travel the Mississippi and we watch them grapple with their world of chaos. Why does every gambling film have to be in Las Vegas, I ask you??
Bonus – 1 Gambling Movie to Totally Avoid:
Runner Runner
Taking an entirely fictitious angle, Runner Runner is a 2013 crime thriller with a more technological bend. Following Richie Furst, a former Wall Street executive, this story revolves around online casinos, and an attempt at funding higher education gone awry. The fictitious flick is incredibly fake when it comes to cyber security, as most online gambling sites literally make their business off of being safe. But we watch as Ben Affleck and Justin Timberlake nose this one over horrifically. Didn’t they see this one screaming raspberry at them when they first read the screenplay?
Edited by: CY