Top 5 Gambling Movies since 2000

Our list of the Top 5 Gambling Movies made since 2000

A Potpourri of Vestiges Feature

By Ken Edwards

There are literally dozens of movies that are considered not only all-time classic gambling movies, but some of them are considered all-time classic movies across all genres. Masterpieces such as Casino (1995), The Sting (1973), The Hustler (1961) and The Cincinnati Kid (1965) will stand the test of time and can safely stand alongside any classic movie from any era, across any genre. 

With the Academy Awards Season recently completely, we invariably speak in melancholy terms andsometimes like to compare films across different eras and bemoan that ‘the movie industry’s best days are behind it’. 

Today we do our best to debunk that theory and look at the Top 5 Gambling movies released this millennium since the year 2000;

1. The Cooler (2003)

William H. Macy performance as Bernie Loots is superb. Loots is the professional loser (‘cooler’) of the title – a man whose luck is so woefully bad that Vegas casinos employ him to repair their house edge by jinxing nearby punters on hot streaks. The gambler’s luck always turns from bad to worse, until the cooler’s own fortunes begin to change for the better after a fling with a waitress. Loots’ discovered good luck is a bad career move and much to the annoyance of the casino bosses that employ him.‘The Cooler’ is a fun look into the roles of luck, fate and superstition in life and became an instant classic.

2. Owning Mahowny (2003)

Proving that 2003 was a classic year for gambling movies, ‘Owning Mahwony’ is the iconic and true story of Dan Mahowny, a Toronto bank manager who at first seems like a boring professional Canadian, probably doing no more than playing online casinos occasionally through

What unfolds onscreen is the biggest bank-fraud case in Canadian history. In his position, Mahowny has access to a multimillion dollar account, eventually leading him to lose CAD$10 million in only 18 months. Hoffmann masterfullyportrays Mahowny’s obsession with losing total control, rather than that of the thrill of the win.

3. 21 (2008)

Another dramatisation of a true story, ‘21’ is the tale of a group of wunderkind MIT students. The movie stars Jim Sturgess as the genius of the student group and Kevin Spacey as the maths professor who trains the groupto count cards and win fortunes on the Vegas strip every weekend. What plays out is a complex tale of casino gambling, Blackjack card counting, betrayal and partying that incredibly and unbelievably, really happened.

4. Casino Royale (2006) 

The film based on Ian Fleming’s stars Daniel Craig, in his first reprise of James Bond, 007. Set at a blisteringpace, the tale follows Bond as he takes on archetypical super-villain, the Poker-playing, Le Chiffre. A gripping scene in the movie centres on an amazing showdown in the Monte Carlo Casino when Bond takes on his nemesis in an all-or-nothing high-rollers-only Poker game. The pace is relentless, co-star Eva Green is gorgeous and the poker play is faultless.

5. Two for the Money (2005) 

Director D.J. Caruso's masterpiece ‘Two for the Money’ stars Matthew McConaughey as Brandon Lang, a former college quarterback. Suffering a career-ending injury, Brandon turns out to have talent at picking winning football bets. He comes to the attention of his mentor Walter Abrams (played masterfully by Al Pacino), a somewhat successful business tycoon with a gambling addiction, who runs a phone-in sportsbook. Walter brings Brandon to New York and introduces him to a luxury, big-money lifestyle. Everything goes swimmingly until Brandon picks begin to lose and havoc breaks loose.

Readers, please feel free to share your opinion by leaving your comments. As always your valuable thoughts are highly appreciated!  

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