Gambling is undoubtedly a compelling topic that makes for great cinema. This high stakes world provides the perfect backdrop for revealing the complexities of human emotion, unleashing great action scenes, dialogue full of wise cracks, and an undeniably entertaining time. Whatever type of cinematic entertainment you’re looking for, you can stake your bet on these movies.
While The Hustler’s promise of a story revolving around pool is what drew viewers in, the way it tackles complex psychological themes is what makes it an undeniable classic. Paul Newman shines in his breakthrough role as an A-list Hollywood actor, fueled by a unique twist that continues to weigh heavily on current and future attempts at any movie that explores human vulnerability. It’s a must-see film for pool players, psychology students, and fans of gambling-related cinema.
Runner Runner features Justin Timberlake as a Princeton grad who’s been swindled in a game of online poker, leading him to confront Ben Affleck, an online gaming tycoon who becomes his mentor. With its realistic portrayal of the online poker explosion that happened around 15 years ago, Runner Runner is an entertaining take on a topic that hasn’t been tackled this extensively since the Unlawful Internet Gambling Enforcement Act of 2006 killed off most online poker sites. Since then, online casinos have become the primary gambling platform for players around the world. In fact, a review of the LeoVegas casino app by Sandlot Games reveals how many of the very best digital providers now host as many as 1000 different games – which is a lot more than your standard land-based casino that features in Hollywood movies. Described by many critics as “The Devil’s Advocate of online gambling,” there’s no question that Runner Runner has made its mark on gambling-inspired cinema. And despite mixed reviews, there’s no denying that this is the movie that made online gaming cool.
If you’re looking for something lighter, check out Mississippi Grind. We’ve previously covered how this film is arguably the mainstream counterpart to the comparatively unconventional card shark story of The Gambler. Protagonists Ben Mendelsohn and Ryan Reynolds exude an undeniable charm that lends an undemanding air to an otherwise dark tale, resulting in a near-perfect weekend movie that tickles the mind as much as it entertains.
Another Paul Newman classic makes the list, but this time he’s accompanied by fellow Hollywood legend Robert Redford. The Sting follows these two as they play two grifters who devise a long-term con to steal money from a dangerous crime boss. Along the way, their complicated schemes entail recruiting a talented group of fellow misfits and con artists who are each promised their own share of the final take. Sound familiar? That’s because The Sting was one of the first highly successful heist movies to come out of Hollywood. Mental Floss recalls how it bagged the Best Picture Oscar along with several others soon after its release, a testament to its right balance of comedy, crime, murder, and drama. If you’re sick and tired of all the heist movies that have come out in the last decade or so, go and see how it’s supposed to be done.
Fantastic dialogue, extremely risky deals, calculated doses of realistic violence, and comedic legend Adam Sandler disappearing into his greatest dramatic role of all time —what more can you ask for? In the tradition of The Hustler, Uncut Gems is a vivid exploration of human frailty and the consequences of even the most calculated risks. Do not be fooled by the fact that this movie was snubbed by the 2020 Golden Globes. If you’re picking just one movie from this list, you can absolutely bet on Uncut Gems for an entertaining albeit jarring gambling movie experience.