The Funniest Gambling Movies to Watch

Gambling movies are often thought of as suave and sophisticated, but they can also be hilarious. The best and funniest gambling movies take a sidelong look at the absurdity of society through the lens of chance-based gaming. Some of the greatest gambling movies aren’t overtly comedies, but they always contain funny elements, allowing us to laugh at the antics of the characters while enjoying the trappings of Vegas cool (and all the hollow glamour it brings).

gambling movies

We’re about to run down the funniest gambling movies you can watch right now. Before we do, why not set the ambience? Decorate your house like a Vegas casino, fire up a great site like Novibet and try out some casino games, or even invite a bunch of people over for a casino movie party. However you decide to do it, immersing yourself in the ambience of a casino can really help to appreciate these works. Here are the funniest gambling movies you can check out right now.

Ocean’s Eleven (dir. Steven Soderbergh, 2001)

The sequels to this snappy reboot are the textbook definition of diminishing returns, but for the 2001 “original”, the stars aligned. George Clooney, Matt Damon, and the rest of the ensemble cast are dazzling as a group of chancers who decide to pull a heist on one of the biggest Vegas casinos in the city. Ocean’s Eleven isn’t a comedy, but it certainly has some great one-liners, and Clooney and his pals are endlessly watchable, even if the narrative is a little creaky. The recent all-female Ocean’s 8 reboot is also worth checking out, although it doesn’t take place in a casino.

The Hangover (dir. Todd Phillips, 2009)

Despite Phillips’ unfortunate comments regarding “woke comedy” (news flash, Todd, that’s not what’s killing funny movies), The Hangover remains the high watermark of his career. Phillips’ ode to boozy stag nights in exotic locales sees Bradley Cooper, Zach Galifianakis, Ed Helms, and Justin Bartha partying to excess as The Wolfpack in Vegas. Naturally, their night quickly goes south, and the group must spend the rest of the movie figuring out what happened the night before. As with Ocean’s, the sequels suffer from diminishing returns, but this first movie is something special.

Fear and Loathing in Las Vegas (dir. Terry Gilliam, 1998)

This isn’t a true casino or gambling movie per se, but it’s a great odyssey into the weirder and darker side of American subcultures. Johnny Depp is the eternally soused Raoul Duke, a thinly-veiled version of the original novel’s writer Hunter S. Thompson, while Benicio del Toro plays his companion Dr. Gonzo. Fear and Loathing was apparently a real wild ride to make, and that’s reflected in the movie’s outre artistic style and sense of countercultural abandon. While there aren’t many casinos or gambling establishments in this movie, Fear and Loathing truly reflects the absurd spirit of Vegas.

What Happens In Vegas (dir. Tom Vaughan, 2008)

Don’t let this movie’s sniffy Rotten Tomatoes rating fool you; it’s actually a great time, albeit one in which you’re not going to find any challenging or provocative laughs. Ashton Kutcher and Cameron Diaz play a couple who marry after a drunken night together, only for Kutcher’s Jack to win a three-million-dollar jackpot at a casino. What follows is a farcical look at the way marriages are made and broken, as well as a great opportunity for some fun Vegas sightseeing. You’ll see the ending coming like a freight train, but that’s no excuse not to spend some time in this movie’s company.

Last Vegas (dir. Jon Turteltaub, 2013)

Four old friends go to Las Vegas in order to host a bachelor party for the last remaining member of their group who’s single. These four friends are played by Robert de Niro, Morgan Freeman, Michael Douglas, and Kevin Kline. If that doesn’t sell this movie to you, we don’t know what will. Naturally, there’s plenty of casino action in Last Vegas, but it’s also a good-natured, good-humoured look at the way older friendships and relationships work. Again, it’s not going to win any prizes for originality, but it’s a perfectly pleasant and fun way to spend a hundred minutes.

The Sting (dir. George Roy Hill, 1973)

If you’ve ever expressed any kind of disdain for “old movies”, then The Sting is the movie that should make you look past that prejudice. It stars Robert Redford and Paul Newman, both of whom are on fire as con men looking to execute a masterful yet convoluted plot involving betting. The poker game scene is legendary (if perhaps factually inaccurate), but it’s the dialogue and snappy sense of movement that will make you want to stay all the way to The Sting’s thrilling conclusion. Give this one a look, even if you don’t usually like “old movies”. You won’t regret it.

Focus (dirs. Glenn Ficarra and John Requa, 2015)

Will Smith and Margot Robbie carry what would otherwise be a fairly mediocre movie. Focus is great fun largely thanks to the chemistry and talent of the two leads, but it’s also a solid casino heist movie in its own right. Smith is Nicky, a seasoned grifter who meets Robbie’s inexperienced Jess Barrett and shows her the ropes. The plot then takes in various situations involving betting, as Smith and Barrett try to con their way to a better life and a bigger payout. Like many of the other movies on this list, Focus is no masterpiece, but it’s great fun while it lasts.

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