Good day frenz, I hope life is treating you just as well as it is treating me right now. I spent a night in the not so distant past live-tweeting one of my favorite Gambling Movies of all time, “Rounders”, so it got me thinking that because Gambling has been one of my main interests for a good chunk of my adult life that I might as well get down on a quick “5” of my favorite gambling movies. If you want a quick gambling tutorial, check out these flicks…..
5. Let It Ride – Horse racing is basically dead in America, but there was a time when going to the track and betting on the ponies was a well travelled path of Americana. This comedy takes you through a day of hilarious side plots and degenerate gambling to a dramatic conclusion……it’s fun, but it also shows you a form of gambling that is no longer mainstream.
IMPORTANT GAMBLING LESSON – “Fade the public” – In the final stanza the lead character Jay Trotter (Richard Dreyfuss) walks around the track and asks people who they like in the final race and literally crosses off all of those horses until he’s down to the horse that nobody liked, that’s his choice. In gambling fading the crowd is often valuable because of pricing, if a good chunk of the public is on one side of a bet, that side is often mis-priced due to the demand.
4. The Sting – This movie features many short cons and a LOOOOONG Con as well as some terrific acting. It’s the oldest film on this list and one that I first saw when I was a child. My favorite scene is the poker scene on the train. You’ll need to check it out to know WTF ole ‘Loaf is talking about.
IMPORTANT GAMBLING LESSON – “Know who you can trust“ – It’s not enough to have a gambling angle and a willing participant, but you need to know who ELSE might be trying to take a shot at you in this endeavor
3. Casino – Frank “Lefty” Rosenthal and Tony Spilotro are two legendary characters in the 70’s Las Vegas scene and this movie chronicles the life and times of these two and others. The movie is from a time and place that people still romanticize when it comes to Las Vegas, long before the major consolidation of casinos and the shift from gambling as the main business to tourism. I’m only 40 years old, so my first visits to Las Vegas weren’t until the early 2000’s, so I didn’t get to really enjoy any of this, but I did get to Vegas early enough to enjoy before “downtown” was rejuvenated. I could go on and explain the plot of the movie, but I won’t because if you haven’t seen this movie, you just need to go see it. The movie crosses the old mob classics into gambling lore. Yours truly is on the hill that this film is BETTER than Goodfellas. Watch them back to back to judge. It’s an all-timer.
IMPORTANT GAMBLING LESSON – “Leave Ego at the Door“ – Ace Rothstein fucked up everyone’s shit by letting his Ego ruin him in several big situations. 1. Marrying Ginger (played by Sharon Stone) 2. The County Commissioner 3. Dispute with Nicky. All of these were spots where if he chooses with his brain and not his YUGE Ego, he gets through and doesn’t end up in the spot he ends up in, which is out of the business and back to his original gig of handicapping sports.
2. Rounders – Before the poker boom, Brian Koppelman tossed this gem out to the general public without much fanfare, but before you knew it, it became a cult classic. Mostly everyone you knew at your local poker game was doing a Teddy KGB impression and using the poker vernacular they picked up from this film. This movie also has lots of good gambling lessons within and a bunch of big no-no’s including playing with your entire bankroll on the table. Every time I watch this film, I pick up some other little phrase or word that I know now but never noticed back then. The attention to detail is terrific and the story line is also great. Even if you don’t already love gambling, you’ll enjoy this Matt Damon / Edward Norton classic.
IMPORTANT GAMBLING LESSON – “Don’t over bet your bankroll” – The opening scene of the movie has your main character Mike McDermott playing a high stakes game with his ENTIRE BANKROLL on the table. Big no-no if you plan to gamble for a living. Truth be told, its not terribly bright in other facets of life either. He forgot to follow the cardinal fucking rule “Always leave yourself outs.”
1. Diggstown – If I were a betting man….AND I AM….I’d bet most of you reading this have never even seen Diggstown, well get your ass in front of a screen and check this movie out RIGHT. DAMN. NOW! Setting up a big gambling situation takes a lot of actors and the right mark, as you’ll see in this great film and ego and greed. James Woods is terrific (forget his politics, if they aren’t your cup of tea, the man is a great actor)….Bruce Dern is the perfect villain in this film. There is even an young, nubile Heather Graham for those that just want a little scenery with their gambling movie.
IMPORTANT GAMBLING LESSON – “Never con a conman, especially one that’s better than you“- Anytime you get offered an incredible bet that seems so obvious that it will win, THINK TWICE. Good gamblers will think of an angle you didn’t and take advantage of you. Just read any of a million stories about Amarillo Slim prop bets and you’ll understand what I mean. Even if you think you have all the details covered, remember what you are up against.