Bet On These Gambling Movies Streaming Right Now
Poker, craps, blackjack - it's all covered in the great gambling movies available to stream
The gambling movie comes with built-in stakes, considering every bet made carries a certain amount of risk. However, the gambling movies we have chosen raise the stakes in different ways, so that more than just money is on the line. These characters, most of them extremely reckless, have made choices that put them in tight spots, which always makes for cinematic gold.
Turn one of these on this weekend if you’re looking for the rush that comes from going all in… on life. (I just gave away a movie tagline for free there, didn’t I?) In addition to these, we’ve also written about other gambling movies like Rounders and Win It All in previous newsletters, both streaming on Netflix right now.
Drew recommends…
Hard Eight (streaming on Amazon Prime)
A gambling movie that doesn’t actually show that much gambling, Hard Eight is a remarkable character study of a lonely former mobster trying to escape his past life. It’s a patient and tender film about regret and redemption that happens to be set in the casinos of Vegas and Reno.
Hard Eight is the debut of one of the great directors working today, Paul Thomas Anderson. Before he went on to create magnificent works like There Will Be Blood and The Master, he directed this minor portrait of Sydney (Philip Baker Hall), a successful professional gambler that comes across the miserable and desperate John (John C. Reilly). Sydney takes John under his wing and teaches him how to make it as a pro gambler.
For a first-timer, Anderson wrote memorable characters that inspired curiosity about their pasts and interior lives. In addition to Sydney and John, Gwyneth Paltrow plays a cocktail waitress that gets mixed up in a bad situation with John. Samuel L. Jackson appears with his typical scene-stealing swagger. And the late, great Philip Seymour Hoffman showcases his considerable talent in a single scene as a loud and obnoxious craps player that you won’t easily forget. If nothing else, Hard Eight is a great chance to watch early performances from actors that went on to bigger things, as well as an empathetic central performance from one of the great character actors in Philip Baker Hall.
The making of Hard Eight was not a happy time for Anderson, as the visionary director was locked out of his own production after quarreling with the producers. They re-edited his film and changed the title from Sydney to Hard Eight. Still, the director got his way when the distributor released his edit instead of the producers’, despite keeping their title. Even after all of the behind-the-scenes issues, this is a remarkable little movie that deserves more love.
Molly’s Game (streaming on Netflix)
If you find yourself thrilled by the rapid-fire dialogue of The West Wing, The Social Network, and A Few Good Men, this is a gambling movie you can probably get on board with. Molly’s Game is screenwriter Aaron Sorkin’s directorial debut -- and it is a very Sorkin-y movie. The characters deliver his clever banter at a head-spinning pace, while shuttling us through the alluring and dangerous world of high-stakes poker.
Based on the true story of Hollywood “poker princess” Molly Bloom, Molly’s Game shows you how a former Olympic-level skier came to run the most exclusive high-stakes poker game in the country, which attracted mega-famous celebrities like Tobey Maguire, Leonardo DiCaprio, Ben Affleck, Alex Rodriguez, and the Olsen twins. These games also brought in shady Russian mob figures that led to Bloom’s arrest by the FBI.
Jessica Chastain plays Molly as an ambitious and driven woman that simply doesn’t know when to stop or slow down. Chastain is more than up for the challenge that comes with Sorkin’s writing, as is Idris Elba as her criminal defense lawyer. Molly’s Game also features solid supporting turns from Jeremy Strong (Kendall from Succession) and, hilariously, Michael Cera, who appears as Player X, an unflattering character that is essentially a stand-in for poker-mad actor Tobey Maguire.
It feels like Sorkin is just out of reach of something amazing with Molly’s Game. I really liked parts and really didn’t like others. The early scenes crackle with fast-paced energy, but the movie is too long and loses its way in the home stretch as he ends up sympathizing with Molly a bit too much. However, there’s no denying how fun it is to watch this glamorous and enticing world of celebrities and billionaires betting absurd amounts at the poker table.
Billy recommends…
Mississippi Grind (streaming on Netflix)
Yet another movie that turns on and you think, “Oh! This is an A24 movie!?” In typical A24 fashion they take a typical movie archetype and make it their own. A movie starring the loud superstar Ryan Reynolds and the “that guy” of the 2010s in Ben Mendelsohn seems like you could predict the dynamic of this movie. The dynamic starts off the way that we expect, with Reynolds as the fast and loud-talking Greek god who can talk his way in and out of every situation while Mendelsohn is lurking in the background admiring a personality that he does not have.
We start off Mississippi Grind with two winners. I’m sorry, I mean two wannabe winners. Curtis (Ryan Reynolds) is a casual good luck charm that latches on to Gerry (Ben Mendelsohn). Curtis uses Gerry as his fix-it-up project. Similar to what Ryan Gosling did to Steve Carrell in Crazy Stupid Love. You find a down-on-their-luck loser who seems like an easy person to “improve,” but then in the end, you learn more than the person that you were trying to help. This is a classic movie trope that is in a lot of genres, but I have not seen it in many gambling movies.
In our opening scene Gerry comes in second place in a poker tournament and immediately his lucky rabbit foot is Curtis. Right as the tournament is about to start Curtis comes in hot with a story that transfixes the entire poker table, and also myself. As their relationship blossoms the pace of the movie is intoxicating. They go on the road in what seems like a casual gambling trip that will end up on NOLA. Each mile brings up a different problem and as their problems come to the forefront the pace slows down just as fast. Not in a bad way, but it is a shift that could make or break this movie for the viewer.
Mississippi Grind has the archetype of a movie that is predictable, but uses that allure to show something that is unique. All while creating the fun gambling sequences that propel us forward through the heartbreak and emotional moments. Reynolds gets the movie started and Mendelsohn will take the movie home. This movie will zag to the point of annoyance, but by the end you will enjoy the emotional connections with these characters.
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