Casino Films with the most Dramatic Losses

Hollywood has a penchant for glorifying gambling. From the James Bond Series to the Fast and Furious, the Office to the Big Bang Theory; lots of movies and TV shows feature gambling scenes. And while many of them end with star characters winning large sums of money, some films have taken an entirely different approach.

A few films share stories of seemingly great people who took a chance at casinos but paid the price by losing it all. Here are a few such movies.

High Roller: The Stu Ungar Story

Imagine living a life so rough that you had to survive playing poker in the streets to survive. Then you turn out into a prodigy and start beating the Pros. And before you know, you’ve won three World Series of Poker tournaments (the only person to do it) and a $50 million fortune to show for it.

But in between the joys of being a self-made millionaire and living the gambling life, you lose it all. Literally: no money, no friends, just you. That’s the story of Stu Ungar, one of the best poker players the world has ever known.

In his posthumous biopic, The Stu Ungar story showed the dark side of being a gambling addict explicitly. The film shares the full story of Stu, from his early beginnings to his untimely death in Las Vegas. The hard-hitting drama film doesn’t share the specific amounts Stu lost per horse racing bet, but it explains he lost over $50 million through gambling and drug addiction.

The Gambler (2014)

Gambling addiction spares no man, not even a college professor from a well-off background. In the 2014 remake of ‘The Gambler,’ Mark Walberg plays a self-destructing lecturer (Jim Bennett) who gambles so much that his entire life revolves playing cat and mouse games with his debtors.

Despite having hundreds of thousands in debts, Jim continues to gamble money in the hopes of hitting one big win. His favourite game is roulette, and he prefers to on the ball landing on a black pocket no matter how many times he loses.

In the course of the film, Bennett loses over $400,000. But after convincing one of his students, a college basketball player, to fix a match through point-shaving, he wins enough money to pay all his debtors. The film ends with Jim as a broke man, but free from debt.

While the Gambler ends a free man, most real-life gamblers have a fate similar to Stu Ungar. Extremely wealthy athletes sometimes lose millions of money and recover, but a few have gone down completely broke.

Learn more about famous sports personalities who lost life-changing money through gambling addiction on this page. Some of them still gamble to date, surprisingly.  Others are serving time in jail while some are still active in sports.

The Cincinnati Kid

Although a casino movie classic, the Cincinnati Kid has one of the most controversial endings ever. The movie’s entire plot builds on the premise of a young poker expert wanting to beat the best player in town. And in doing so, he can become the undisputed poker champion.

The Cincinnati Kid is a low-budget film set in the great depression era. As such, it’s not flashy or graced by high-rolling players. Nonetheless, it’s gripping and dramatic as ‘the kid’ battles distractions to beat “the man.”

Eric Stoner, the kid’s film name, and Lancey ‘the man’ Howard’ manages to outfox their opponents to the last hand when they meet. By then, Lancey looks tired and loses a few hands convincingly. But to the surprise of nearly everyone who watched the film, Eric loses to “The Man’s” straight flush.

Lost in America (1985)

Lost in America has a gambling scene thousands of casino players can relate to. A crazy in love couple opts to leave L.A. to tour America with their $100,000 savings. They have an RV to make their money last for a while.

Unfortunately, the newly wedded couple drives to Las Vegas where a quick stopover obliterates their plans. While the man’s away, the bride gets curious and settles around a roulette table with a bag full of cash.

Predictably, she catches a gambling bug and spends the entire nest of money. It all happens so quickly that even the pit boss is afraid to tell the woman’s husband what had happened.

“She hasn’t been on a lucky streak,” the pit manager tells the husband who’s visibly dismayed.

Although a film, everyone who watched the scene was probably shocked as well. The husband wasn’t even gone for ten minutes before the wife lost the money. Sadly, such split-second losses happen all too often in Las Vegas and online casinos.

Indecent Proposals (1993)

In “Indecent Proposal,” Hollywood shows us why it’s possible to gamble both your money and your wife and lose both. Billionaire Robert Redford offers Woody Harrelson $1 million to sleep with his wife, Demi Moore.

To put some context, the couple had just lost their entire fortune in a game of roulette. But Redford, who spotted the couple, got attracted to Demi. Both Demi and Robert me in high school and have been in love ever since. But having lost their fortunes and a billionaire offering so much money, their marriage nearly comes to an end.

Bad Lieutenant (1992)

Before Nicholas Cage and company remade it, Bad Lieutenant focused on a cop criminal with an irredeemable path towards self-destruction. He’s a drug addict, an alcoholic, a lawbreaker and a gambler. He doesn’t have a name. Bad Lieutenant is just a lousy lieutenant doing everything police officers and civilians at large shouldn’t do.

Amidst his gambling problems, Bad Lieutenant drunk drives through the Bronx after he just lost a lump sum to baseball betting. He feels gut-wrenched and shoots his car’s dashboard in broad daylight. Of course, he doesn’t quit gambling. Quite the contrary, Bad Lieutenant attempts to recoup his losses by doubling down in his next bet.

The film doesn’t give Bad Lieutenant redemption, also. After losing most of his money through gambling, he wins once and gives the money to a group of rapists but condemns them to leave New York. Shortly after, he attempts to park his car, and another drive drives close by and shoots him dead.