Movies & TV

Place Your Bets: Four of the Best Gambling Movies Of All Time


roulette wheel

There is something irresistible about a gambler. Brimming over with an optimism that we all wish we could share, they’re roguish, charming, and they refuse to play by the rules, all of which makes them the perfect anti-heroes.

It’s impossible not to get caught up in the suspense when we watch them on our screens. Seeing the dice roll and the sharp, accompanying intake of breath, we can’t help rooting for our risk-taking protagonists, so it’s unsurprising that Hollywood has taken such stories and turned them into big-budget films time and time again.

If you’re at a loose end and looking for something enjoyable to watch, here are a few of the best gambling movies of all time for you to try…

#1: Molly’s Game (2017)

Molly's Game Jessica Chastain

Filmed right here in Canada, Molly’s Game is the most contemporary choice on this list, but it carries on in the proud tradition of the many gambling films that came before it by adopting slick dialogue and an irresistible storyline. Following the real-life tale of ‘Poker Princess’ Molly Bloom, it charts her meteoric rise to success, from her beginnings as a failed Olympic athlete to her arrest in 2013 for illegal gambling. Addictive, enthralling, and in parts genuinely adrenaline-inducing, it will keep you on the edge of your seat from start to finish.

#2: Rounders (1998)

Rounders features a sterling cast that includes a young Matt Damon, Edward Norton, and John Malkovich. It might be two decades old now, but it has lost none of its charm in the intervening 20 years. Following the story of an entrepreneur who funds his university fees by making a killing at the poker table, it culminates in a deliciously high stakes games. With inimitable performances, authentic portrayals of poker strategy, and the wittiest of dialogue, it will make you feel ready to head down to the casino yourself and see what fate has in store for you when the cards come out. If you’re feeling like giving something different a go, you could always give in to that urge and play a hand of video poker, or even live casino poker by visiting a website like casinogames.ca to select a casino that offers such variants.

#3: Casino (1995)

Robert De Niro Casino Las Vegas Movies

Another real-life story turned cinematic masterpiece, Casino marries the mastery of Scorsese with the dazzling dramatizations of Robert De Niro, Joe Pesci, and Sharon Stone. Widely hailed as the ultimate gambling movie of all time, it will have you hooked in an instant, so that even when you feel like you should be looking away, your eyes remain glued to the screen. Following the story of a bookie who runs Vegas casinos on behalf of mob bosses, it provides a dangerous glimpse into the darker side of rolling the dice, and has some of the most memorable scenes in silver screen history.

#4: Hard Eight (1996)

It may lack some of the glamour and thrill encapsulated by the other movies on this list, but Hard Eight also deserves a place here. Focusing on bringing to life a human story and a compelling cast of characters, it follows Phillip Baker Hall, a past-his-prime gambler who becomes a father-figure to a down-on-his-luck youth. Poignant yet nonetheless precise in its depiction of gambling schemes and their unique ingenuity, it really is well worth a watch.

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