Always double down on... 11 Hollywood Tips on Becoming a Better Gambler

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A wise man once told us, “the best throw of the dice is to throw them away.” Wise words indeed. Then we discovered that the man had read it in a fortune cookie, and unwilling to gamble away our entire life savings on the word of a complimentary Chinese takeout snack, we went looking elsewhere for our gambling advice. As it turns out, Hollywood is positively teeming with tips for the avid gambler, from the obvious (“Always bet on black”) to the not so obvious. This got us thinking. With so many great movies centered on the art of gambling, surely we could become successful high rollers just by digging in to our DVD collections. Below you’ll find a list of helpful tips for everything from the poker table to the pool hall, while reliving our favorite movie moments along the way.

Always double down on 11... unless you're playing a $100 table and you've only got $300. (As seen in: “Swingers”)
Las Vegas may sound like the perfect getaway for a broken heart, but from the moment Mike and Trent (Jon Favreau and Vince Vaughn) arrive, things are bound to go wrong. For starters, they don’t go to the hottest casino on the strip, but rather an old school joint where seniors go to die, and “high rollers” like them can score a free night with a few lucky ladies. Unfortunately, the night gets off to a disastrous start when Mike heads to the high rollers table and stumbles into an excruciatingly uncomfortable exchange between him and the dealer. After cashing in his entire bankroll and getting back only three black chips, he soon discovers he’s stuck at a $100-minimum-bet table. His first hand yields an 11, sending Mike and Trent into hilarious banter about the age-old rule of the double down, and eventually, Mike gives in. His third card gives him a respectable 18, but the dealer squeezes out a blackjack, killing his night before it even begins. Still, despite spending the next few hours playing alongside a prostitute, a biker and a lucky old woman, at least poor Mikey had the chance to sleep with a Dorothy.
– Jason Zingale

Don't gamble drunk. (As seen in: “The Hustler”)
Excessive drinking degrades your judgment while lowering your inhibitions and, when you’re gambling, that’s dangerous. And if you’re gambling at pool, where both nerve and coordination are vital, drinking is obviously a disaster. That’s exactly what self-destructive up-and-comer “Fast” Eddie Felsen (Paul Newman) learns near the opening of Robert Rossen’s hypnotically bleak classic, “The Hustler.” Facing off for the first time against billiard hall legend Minnesota Fats (Jackie Gleason), Eddie’s considerable skills add up to a miraculous $18,000 win. But it’s not enough. He needs to hear Fats cry “uncle,” so the marathon 25-hour game continues and the bourbon he’s been drinking all night finally takes its toll. Even as Fats insists on taking a few minutes to wash up and refresh himself, Eddie keeps on drinking. Naturally, the younger man winds up losing everything to the unflappable Fats. He’ll meet the legendary old hustler again, but regaining his self-respect will come at the highest price. – Bob Westal

Savants are a blackjack player’s best friend (As seen in: “Rain Man”)
Charlie Babbitt (Tom Cruise) had little use for people, unless they could be exploited for his personal gain. Charlie was even indifferent to the news of both his father’s death and the realization that he had an autistic older brother Raymond (Dustin Hoffman), who lived in a mental institution. Charlie just wanted half of the $3 million inheritance that Charlie’s father left to Raymond. In their cross-country drive from Cincinnati to Los Angeles to discuss custody issues with his lawyers, Charlie discovers Raymond’s amazing recall abilities, and does what any caring little brother would do: he takes Raymond to Las Vegas and uses Raymond’s skill to win a fortune at blackjack. (“Lots of queens, lots of queens.”) Charlie and Raymond do so well, in fact, that the director of security calls Charlie in for a little chat. “You should take your winnings and leave the state,” he says. Hey, if we won $80,000 in a day, we’d walk away, too.
– David Medsker

If you're a spy playing high-stakes poker, mix your own drinks. (As seen in: “Casino Royale”)
When you’re gambling on behalf of the free world, you simply can’t be too careful. But, in the 2006 James Bond series reboot, Daniel Craig’s 007 is still a relatively inexperienced tough who has to learn his lessons the hard way. This time, his obsession with destroying the villainous Le Chiffre, and his own fondness for the new cocktail he’s created (three parts Gordon’s Gin, one part vodka, half a measure of Kina Lillet and a lemon twist), makes him oblivious to a mysterious blonde who adds a deadly dash of digitalis to Bond’s drink. The grueling solution? Drink shakers full of salt and pepper to induce vomiting, then take a nearly deadly dash to his trusty Aston Martin for a call to MI6 and some impromptu poison control. None of the above would have saved his life were it not for a last-minute rescue by the lovely Vesper Lynd (Eva Green). It’s only fitting that he eventually names the ridiculously strong drink after her. – Bob Westal

If you've lost everything, you can always prostitute your wife to a millionaire. (As seen in: “Indecent Proposal”)
In 1993, director Adrian Lyne’s turd of a film “Indecent Proposal” not only provided a cautionary tale to yuppies with no scruples, it gave all of us an invaluable lesson in gambling. Woody Harrelson and Demi Moore play David and Diana, married high school sweethearts who travel to Las Vegas in hopes of winning enough money to finance a real estate project. But as usually happens in Vegas, the house wins and they lose their savings (if only they had seen “Lost in America”). But luckily for them, they are soon approached by suave millionaire John Gage (Robert Redford), who offers the couple $1 million for the opportunity to spend one night (read: have sex) with Diana. Monetary desperation trumps marital vows and Diana spends the night with Gage for the cash. Things didn't go too smoothly for David and Diana in the film, but hey, it never hurts to ask, and after blowing it all at the roulette wheel to begin with, are you really in a position to take the moral high ground? – Andy Kurtz

Never bet the nest egg. (As seen in: “Lost in America”)
David Howard (Albert Brooks) and his wife, Linda (Julie Hagerty), have decided to drop out of society and cruise around America in an RV. Shame they stopped in Vegas, where Linda gambled away their entire nest egg. “Why didn’t you tell me when we married you were this horrendous, gambling-diseased person?” screams David. “It’s like a venereal disease! You tell someone!” He immediately goes to the manager and launches into the most ridiculously desperate pitch of all time, suggesting an ad campaign focusing around the casino giving him and his wife their money back that reaches its nadir when he suggests having Santa Claus hand them the check. (“We associate, for the first time ever, Christmas and Las Vegas. ‘Las Vegas: a Christmas place to be!’”) Unsurprisingly, the Howards retreat from Sin City considerably poorer than they arrived, with David informing Linda that she can’t even speak the phrase “nest egg” aloud -- not even part of it. “If you’re in the forest, you can point and say, ‘That bird lives in a round stick,’ and you have ‘things’ over easy with toast!” In short, my friends, the nest egg is sacrosanct; bet it, and your marriage will never recover. – Will Harris

Never underestimate an opponent’s snack. It could be his weakness. (As seen in: “Rounders”)
“It hurts, doesn’t it? Your hopes dashed, your dreams down the toilet. And your fate is sitting right beside you.” If you’re looking for a quick summary of the first 90 minutes of “Rounders,” look no further than the above quote from John Malkovich’s over-the-top Russian gangster, Teddy KGB. Throughout the course of the film, Mike McDermott (Matt Damon) is exploited, beat up and completely cleaned out. With only one day remaining to pay off his friend Worm’s $15,000 debt, McDermott does the unthinkable – he borrows 10 grand from his mentor and heads to Teddy’s hangout for a little heads-up poker action. It doesn’t take long before McDermott has doubled his money, but just as he’s about to leave, Teddy baits him into another round. McDermott bites, and he pays dearly when the tables begin to turn. Lucky for him, Teddy likes to snack on Oreo cookies (he’ll eat one if he’s got a good hand), and once McDermott recognizes the tell, he exploits the crème-filled weakness for six times his original bankroll.
– Jason Zingale

Never play poker with a gangster. (As seen in: “Lock, Stock and Two Smoking Barrels”)
Guy Ritchie’s debut film is quick to crush any preconceptions that talented gamblers always win, but the bigger lesson here is that you should never trust someone whose reputation includes beating a man to death with a 15-inch, black rubber cock. When poker natural Eddie walks into local porn king “Hatchet” Harry’s high-stakes card game, he’s unknowingly walking in to a trap. With Harry’s right-hand man spying Eddie’s cards through a hidden camera, and then communicating them to Harry via a clever Morse code device attached to his leg, Eddie is slowly baited into the biggest hand of the night. When Harry raises him more than he’s got, it looks like the game is finally over. That is, until Harry offers to stake Eddie the $500,000 he needs to stay alive. If he refuses, he’ll go home empty-handed, but if he accepts, he stands to lose a lot more than money. – Jason Zingale

Never take your eyes off the dealer. They may be dealing from the bottom of the deck. (As seen in: “Maverick”)
The great riverboat poker tournament has come down to a final game between Maverick (Mel Gibson), The Commodore (James Coburn), and a scroungy Spaniard named Angel (Alfred Molina); with Marshall Zane Cooper (James Garner) serving as the lawman for the proceedings. When Maverick spots the dealer dealing from the bottom of the deck, he asks to let Angel deal him his last card instead, and Cooper agrees. The Commodore goes all in (he’s got four eights), as does Angel (he’s got a straight flush), so Maverick joins the fun as well, disconcerting his competitors by refusing to look at his final card. Instead, he lays down his first four cards one by one: 10, jack, queen, king -- all spades. With a sigh and a picture-perfect poker face, he tosses onto the huge pile of chips his final card: the ace of spades. Angel reacts poorly, whipping a gun out of his sleeve, but before his finger ever reaches the trigger, Angel and his men have all been shot dead by Cooper and Maverick. Of course, if you’ve seen the movie, you know Maverick doesn’t actually get to enjoy all of his winnings. But as my pappy always said, “No use crying over spilled milk. It could have been whiskey.” – Will Harris

You're better off playing at the casino than robbing the casino. (As seen in: “Ocean's Eleven” 1960)
Today, Las Vegas is a corporate entity, but in 1960 only one corporation mattered, and you were much better off pretending that La Cosa Nostra, Inc. didn’t exist. In this original, fascinatingly historic (but far less entertaining) version of the ultimate Vegas fantasy, Frank Sinatra’s Danny Ocean and company were never going to emerge triumphant from their bold New Year’s Eve robbery. (Some old friends and employers of Mr. Sinatra and his Rat Pack cohorts might have felt it was sending the wrong message.) Sure, it’s bad luck when one key member of the group (tough guy stalwart Richard Conte) drops dead, starting a series of seriously unfortunate events, but in any case, the whole gang would have been better off betting their life savings on “red.” If “Ocean’s Eleven” were a true tale, Frank, Dean and Sammy wouldn’t be slowly walking down the strip at the end of the movie, they’d be on the I-15 out of town -- or more accurately, underneath it. – Bob Westal

You're better off robbing the casino than playing at the casino. (As seen in: “Ocean’s Eleven” 2001)
Sure, casino gambling can be a blast, but unless you’re counting cards (accurately), the house always wins. Always. If you actually want to make money from casinos, try owning them, or, failing that, robbing them. The first entry in Steve Soderbergh’s heist trilogy is more of a fantasy than “Lord of the Rings,” but the basic truth of this masterpiece of slickness is that the cool cats led by George Clooney and Brad Pitt are much too smart to seriously play table games for anything more than chump change. It’s much more rewarding, and apparently much more fun, to play the more high-stakes game of using absurdly high-tech equipment to rip off a nasty casino owner (Andy Garcia). And, before it’s all over, they get to spend a relaxing moment enjoying the Bellagio’s famous fountain before making off with their winnings. Sure, they might not be completely out of the woods, but they’re newly wealthy and way too hip to wind up in dead or in jail. – Bob Westal

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