Top 10 Degen Gambling Flicks

By Pauly
Las Vegas

The Sting. The Hustler. Rounders. The Cincinnati Kid.

Those are among Hollywood's brilliant contribution to the gambling film genre. California Split (with Elliot Gould) is probably the best poker flick you never heard of, while Croupier (with Clive Owen) captures the essence of gambling.

Let's go a little deeper and broader into the film archives with ten films off the top of my head that involves some sort of degenerate gambling. I wish I had more time to do a thorough investigation and smoke a bag of dope while analyzing 130 different flicks. Maybe after the WSOP? Until then, here's the Tao of Poker's Top 10 Degen Gambling Flicks...

1. Lucky Girl (2001)

Way before Elisha Cuthbert became the NHL's pin cushion, and before she gained fame as Jack Bauer's daughter from 24, Cuthbert starred in a Canadian film titled My Daughter's Secret Life. Typical good girl gone bad tale about a high school girl who becomes addicted to gambling, spirals out of control (in a very Canadian-after-school-special kinda way), and eventually has to shoot porn to pay her way out of debt. During her downfall, she goes on a wild bender betting on sports, stealing her mother's credit card to sign up for an online casino, and carousing in underground gambling halls. The original title was changed for release in the U.S. on the Lifetime network under Lucky Girl.



2. Let It Ride (1989)

Jen Tilly hijinks. Who could ask for anything more? How about a lifelong loser (Richard Dreyfuss) who embarks on the rush of a lifetime at the race track. He can't lose a bet...



3. Trading Places (1983)

I was 17 and worked as a runner on the floor of the NY Commodities Exchange, which is also the locale of the final dramatic scene of Trading Places takes place. In fact, one of my bosses can be spotted in one of the pit scenes towards the end. Anyway, if you don't know the comedy was an interpretation of Mark Twain's novel The Prince and the Pauper. Two rich brothers, Mortimer and Randolph Duke, have a prop bet if they can transform a street thug into a successful businessman -- and vice versa. Billy Ray Valentine is arguably one of Eddie Murphy's greatest roles. Bo Didley makes a cameo as a pawn shop own and utters one of my favorite movie lines... "In Philadelphia, it's worth fifty bucks."



4. The Deli (1997)

John A. Gallagher wrote/directed The Deli, a comedy about a New York deli owner who is in over his head with gambling debts. His sweet old mother gives him money to play the "numbers" every week, but he has been pocketing the money because she's never won once in 40 years. Disaster strikes when his mother's numbers hit -- he has to cover her jackpot winnings, in addition to paying his deli debts and sports betting losses. Interesting side note... Amnon Filippi's brother, David, makes a cameo in the film.

Sorry, no video clip for The Deli. Go look for it on Netflix.

5. Owning Mahowny (2003)

In my estimation, Philip Seymour Hoffman accurately depicted a total degen in one of the most nauseating gambling films in history. Based on a true story about one of Canada's largest single-man bank fraud operation, Mahowny (Hoffman) embezzles money to covering his staggering gambling losses during sojourns to AC and Vegas. There are two scenes in all of cinematic history that I cannot watch: the Mike/Nikki phone call scene in Swingers, and the one in Mahowny when he tells his bookie to bet on all the home teams in the National League.



6. Rogue Trader (1999)

In the 1990s, Nick Leeson took down Barings Bank -- at the time the oldest and one of the most prestigious merchant banks in the British Empire. Leeson (Ewan McGregor) is the legendary derivatives trader based in Singapore who abused his firm's error account and racked up over $1.4 billion in losses gambling, most of it on arbitraging the Japanese stock market and other Asian markets. Just another sad story about a compulsive gambler who chases his losses, only to ruin a bank's 233 year reputation in the process.



7. Two for the Money (2005)

The lemon soliloquy by Al Pacino in Two for the Money is one of the most true and eloquent scenes explaining compulsive gambling. The film delves deep into NFL gambling tout services.



8. Eight Men Out (1988)

Baseball flick. Era piece. Shoeless Joe Jackson. Ensemble cast. What could be better than Eight Men Out? Director John Sayles shared his take on the Chicago Blacksox scandal based on a book by Eliot Asinof. Arnold Rothstein bribes members of the White Sox to take a dive in the 1919 World Series, which was a best of nine series back then. I love a good fix. And I love movies about fixes.



9. Diggstown (1992)

James Woods unleashes a forceful performance as con man Gabriel Caine in Diggstown. Upon his release from prison, Caine makes an outrageous wager that he knows a boxer who can knock out 10 boxers in a 24 hour period. Just when you think the fix is in... there's a twist.



10. Wall Street (1987)

I had to throw in Oliver Stone's Wall Street because it's a film so close to my heart, and like so many young men eager to strike it rich, I also got hooked by the "Greed is good" mantra. Some days I can tell if the film is an indictment on 1980s excess or a justification for the anarchy and corruption in today's financial sector.

That's it for now, but please let me know if you've come across any obscure gambling flicks.