Shuffle up and deal
The 5 greatest gambling movies of all time
Some of the most underrated movies are gambling movies. On this list, we focused on gambling being the key element. A movie like Casino, for instance, has gambling, but at its heart it is a mafia movie. The Sting is a classic, but it would fall in the con movie genre. Maverick is good too, but it is more of a Western. There are a lot of great movies that have gambling scenes or backdrops. In the movies on this list, gambling is the fundamental driving force of the plot. These are a must for all degenerates:
5) The Hustler
The classic Paul Newman/Jackie Gleason tale takes us back to a time when gambling was conducted in back rooms and in this case, pool halls. For younger viewers, it represents a bit of a history lesson. While gambling has become mainstream, this was a time of hustlers, con men and shady people. Worth a watch.
4) The Cincinnati Kid
Another history lesson, Steve McQueen is basically Mike McD from Rounders decades earlier. The hot young up and comer who goes against a legend. It again harkens back to a time when gambling was deep underground. It's gritty, and like all gambling stories does not always have a happy ending.
3) Owning Mahoney
Based on a true story, Philip Seymour Hoffman plays a Canadian degenerate gambler who embezzles millions from his bank in order to feed his gambling habit. It is a cautionary tale of what can happen when addiction takes over. It's dark, hopeless and the late Hoffman is amazing in the role.
2) Let it Ride
The gold standard for horse betting movies. Richard Dreyfuss plays a cabbie whose friend overhears a conversation about a fixed race in this little-known gem. After Dreyfuss cashes, he goes on an unprecedented hot streak. It also deals with the social distinctions of the track, from the high rollers to the down on their luck. It features a young, sexy Jennifer Tilly - who is better known now for her real-life poker skills - and Teri Garr is terrific as the drunk wife. A must watch for anyone with even a passing interest in horse betting.
Simply the best, most realistic gambling movie ever made. Matt Damon is terrific as the main character, a brilliant poker player who tries to bail out his friend Worm, played by Ed Norton. John Malkovich plays the iconic Teddy KGB, and John Turturro is Knish, the wise old grinder. Gretchen Mol plays the overbearing, unlikeable girlfriend perfectly. The movie is filled with realistic characters and covers the highs and lows and massive swings of no-limit hold 'em as well as other games. Memorable lines, moments, people...It really is the gambling movie all others will be measured against.
Just missing out
The Gambler with James Caan is another classic. Also, check out Mississippi Grind with Ryan Reynolds, an underrated indie movie.