The Biggest Gamblers In The Movies Always Seem To Lose

Posted: September 12, 2016

Updated: September 12, 2016

Whilst there are a lot of movies that feature mansion casino gambling, in grandiose edifices of betting, or the notorious western saloon poker game that ends up in a shoot out, most films involve risk taking of some form or other and it is surprising how often an entire plot might hinge on a momentary call on the gods of fate to be kind. With this in mind we look at some of the biggest gamblers in the movies and rather than dwell on the heroic success against the odds, we look at how sometimes their luck lets them down.

1. Han Solo – Star Wars

In the grand scheme of things Han Solo making the decision to seek out Lando Calrissian for help proved to be a minor hiccup on the road to galactic freedom in Star Wars. However given he ended up frozen in carbon (hardly the most pleasurable of experiences) and could probably have got the Millennium Falcon repaired somewhere else, the smuggler and rebel leader makes first mention on our list of biggest gamblers who lost – which is slightly ironic given how he gained possession of the ship in the first place, n’est pas?

2. MacDonald – The Great Escape

Losing Movie Gamblers

  • Han Solo: Harrison Ford
  • MacDonald: Gordon Jackson
  • Maj. Strasser: Conrad Veidt
  • Dr. Bowman: Keir Dullea
  • Col. Quaritch: Stephen Lang
  • Joe and Jerry: Tonny Curtis – Jack Lemmon
  • Aragorn: Viggo Mertensen

Intelligence officers not displaying any at all is common movie fodder and MacDonald’s chances in The Great Escape were blown when he replied “Thank You” to a gestapo officers laconic wish of “Good Luck”. You don’t have to be the biggest gambler to hope that a good disguise will get you through an enemy checkpoint, but failing to speak the expected language is silly and anyone in that situation from the UK gambling news of escaped POWs wouldn’t be top of the gestapo briefing that morning is hardly intelligent.

3. Major Strasser – Casablanca

Although perhaps not one of the more obvious of the movies’ biggest gamblers, in a classic scene of cinematography, towards the end of Casablanca, the embodiment of the Nazis, Major Heinrich Strasser, enters the hangar to demand where Victor Lazlo is and then, when informed they’re on the plane, gambles that he can both make a phone call to fighter command and hold a gun over Rick at the same time, perhaps betting his stern impression alone will hold the American at bay. It is a wager he loses.

Casablanca film

An ill-advised wager casuses the demise of Major Strasser in “Casablanca”

4. Dr Bowman – 2001: A Space Odyssey

This is perhaps the most harsh of judgments but given just how advanced Hal was in 2001: A Space Odyssey it seems that one of the biggest gamblers turns out to be Dr. David Bowman who perhaps should have more closely examined the concept of lip reading computers before discussing his concerns with other people. Betting you’re smarter than a computer is like placing a bet on sports in the UK by throwing darts at a copy of Sporting Life, it might be “something wonderful” but not usually.

Colonel Quaritch – Avatar

Any list of the biggest gamblers in the movies who lost has to include Colonel Miles Quaritch from Avatar who bet that modern high tech weaponry can defeat a bunch of seven foot blue primitives armed with big sticks. If you were to find such things at Bet365 you’d probably discover the big guns would have better odds than the bows and arrows, however, alas, the good guys always win, and betting that being the evil corporate stooge driven by profits with no moral compass might pay off for once was a fools wager for the Colonel.

Avatar movie

Colonel Quaritch loses his bet that modern weapons could defeat the Na’vi

Joe & Jerry – Some Like It Hot

Joe & Jerry are not, strictly speaking one character, but dressing in drag to escape being whacked by gangsters, traveling the length of the nation and then running into precisely those gangsters one is trying to avoid, as occurs in Some Like It Hot, is perhaps the very definition of a gamble gone awry and makes them joint entrants in our list of biggest gamblers in the movies who lost. Whether you consider a proposal of marriage from a millionaire who doesn’t mind you’re not a woman or a date with Marilyn Monroe a win or not is up to you, and entirely beside the point.

Aragorn – Lord Of The Rings

Lord of the Rings demonstrates to anyone in the UK gambling laws of averages will see the favorite win most of the time is wrong. Typically at moments of stress the biggest gamblers can be those seeming to back a dead cert. All Aragorn asked was for Legolas the elf super-archer to shoot one orc carrying something marking him out from the crowd, but at the crunch moment the boy from the Mirkwood fails to make a kill shot and merely puts two in the shoulder and as a result Helm’s Deep loses an outer defensive ring to a massive explosion. So much for elf and safety, eh?

LOTR return of the king

Aragon’s faith in Legolas almost costs him his life in the second LOTR film

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