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The Best Books for Aspiring Gamblers

Gambling has fascinated us and has been an integral part of human culture for thousands of years. From the bright lights of Las Vegas to the untouchable old money families of Monte Carlo, the practice of gambling has inspired thousands of stories both real and imagined, which continue to enthral millions of people around the world.

Part of this fascination stems from the sport itself; the risk of the wager, the thrill of the chase, and the euphoria that accompanies a life-changing jackpot win. Dreamchasers have been flocking to casinos for centuries in the hopes of turning their life around and reaching the big-time, and it’s this very dream which readers find so magnetic and enchanting.

The idea that one can completely reverse their fortunes and change their station in life with a simple roll of the dice or a well-played hand is a very attractive and entertaining one indeed. The literature around gambling is a rich and diverse canon, one which includes luminaries such as Dostoevsky and pop culture icons like Ian Fleming and Hunter S. Thompson.

On the other side of the spectrum are the educational novels, which are more popular with those who take gambling more seriously. Everyone from Harvard professors to mathematical prodigies have written guide books explaining how the vast casino system works and what it takes for an average person to rise to the stop and become a high roller.

Whether you’re an aspiring gambler or just fascinated with the cultural heritage of the activity, read on to find out the very best gambling books ever written.

The Best Fiction Gambling Novels

Caption: Casino Royale was a huge box office hit, inspiring many to try their luck at the casino tables.

Sometimes the best novels are borne out of real-life circumstances. This is certainly the case with one of the most critically-acclaimed gambling-themed novels of all time, Fyodor Dostoevsky’s The Gambler, first published in 1866.

The novel follows the glamorous lives and over-the-top roulette and blackjack habits of the Russian aristocracy as they move between the most luxurious hotels in Europe wagering a king’s ransom at the gaming tables.

This sumptuously written text is about more than just roulette, which Dostoevsky himself was an avid player of, dealing with themes of personal greed, societal corruption, and the fracturing of social bonds as a result of a growing culture of individuality.

If the lengthy philosophical ruminations of Dostoevsky are a little too heavy for you, then your best bet is to dive into the uber-stylised world of blackjack, yachts, spies, and gadgets in Ian Fleming’s Bond classic Casino Royale.

First published in 1953 and later turned into a blockbuster film, this gripping action novel follows 007 at his very best, navigating the diamond-encrusted snake pit that is Monte Carlo, where he must win a high-stakes game of baccarat to prevent the winnings going to an international terrorist.

This would be no round-up of gambling literature if we didn’t mention Las Vegas. There are countless novels detailing the stranger-than-fiction exploits of the City of Sin, but none does them justice better than Hunter S. Thompson’s Fear and Loathing in Las Vegas: A Savage Journey to the Heart of the American Dream.

This psychedelic masterpiece is based partly on Thompson’s own Vegas exploits, as he happened to be an avid blackjack player during his life. Rather than following a linear storyline, Fear and Loathing is a whirlwind journey through the dizzying excesses and unconventional characters that inhabit the gambling capital of the world. It’s a text that stays with you long after you’ve finished reading.

The Best Non-Fiction Gambling Books

Caption: From gambling to financial trading, Edward Thorp has certainly capitalised on his skills.

If you’ve read any of the above novels and want to make it in the high-stakes world of casino gaming, the next step is to learn from the best. There are a number of painstakingly detailed and highly informative instructional guides from expert gamblers which you should read if you want to have the best shot of turning your gambling passion into a lucrative career.

Since blackjack has long been the most popular table game at most casinos, that seems like the best place to start. Any experienced gambler knows that the game of 21 is about much more than pure luck, and that you’ll need plenty of skill and attention to detail in order to become a high roller.

One of the most popular tomes, which has sold over 1,000,000 copies as of this writing, is pro gambler Edward Thorp’s Beat the Dealer: A Winning Strategy for the Game of Twenty-One. In it, the original king of card counting lays out his tried-and-tested strategies for beating the house, claiming to have won millions doing so himself.

Then there’s the book described by reviewers as “the book that launched a thousand blackjack careers”. Ian Andersen’s Burning the Tables in Las Vegas: Keys to Success in Blackjack and in Life teaches novices the art of playing a winning hand, as well as the valuable life lessons that blackjack teaches us.

Once you’ve dusted up on your blackjack literature, the next thing to do is follow the advice of these acclaimed authors and practice. Thankfully, in the digital era, aspiring gamblers can now work on their blackjack skills online for free, without having to wager a single penny. Eddy Thorp would have surely killed for such an opportunity.

The Best Audiobooks and Guides

If you’re serious about becoming a pro gambler, then you’ll need to take your studies seriously. Listening to some audiobooks while you go about your day is an effective way to learn more about the rules of gambling without having to sit down and read through a novel.

There are a number of great gambling guides available as audiobooks. One of the very best is the gorgeously narrated The Blackjack Life by Nathaniel Tilton, which systematically goes through all of the golden rules of 21, whilst peppering the information with inspiring lessons on how casino gaming can make you a better, stronger person.

Another good listen is Alexander Fitzgerald’s Exploitative Play in Live Poker, which teaches you how to master the art of the poker face, whilst learning how to read facial cues and know when your opponent is bluffing. Le Chiffre would have appreciated this one. The whole text is available on Audible now and can be listened to for free.

The vast canon of gambling literature is far too extensive to cover in one place, but these are without a doubt the best texts to get you started on your journey to becoming a pro.

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Written by Nathaniel Fried

Co-founder of Fupping. Busy churning out content and building an empire.

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