Top 10 Gambling Books of All Time

Gambling makes for the perfect subject for a great story. You take a risk. You anticipate a reward. The bigger the gamble, the greater the payoff. Bet it all. Lose it all. Win it all. Fundamentally, everything in life is a gamble: the relationship, the job, the family. Simply existing, from day to day, is little more than a series of calculated decisions and risks.

So, it comes as no surprise that authors have put gambling at the centre of many a book; both fact and fiction. We’ve scoured the Internet, and consulted the bookworms, to bring you our top ten list of the most loved books that tell the tale of the tables, put the action in the ante, and bring home the betting bacon.

#1. Fear and Loathing in Las Vegas – Hunter S. Thompson

Written in 1971, Fear and Loathing is Thompson’s hazy, brilliant, tale of a drug-fuelled search for the American dream in the heart of Las Vegas. Insane, incredible, laugh-out-loud-funny, and utterly original, the book introduced the world to gonzo journalism where Thompson is both the author and the protagonist. In brief: the book is all about the end of the 1960s hippy dream, with trashed hotel rooms, drug excess, and the quest for meaning at the blackjack tables of Las Vegas. Darkly brilliant.

#2. Casino Royale – Ian Fleming

s of James Bond on the big screen, but of course he started his career as a spy in print. Ian Fleming’s Casino Royale was first published in 1953 when the character of Bond was introduced to the world. In Casino Royale, James Bond has to play against and bankrupt SMERSH villain La Chiffre at the Baccarat tables. In the 2006 movie the game is changed to Texas Hold’em, but the outcome remains the same. Fleming manages to keep the reader gripped by the use of his sharp and suspenseful prose, punctuated by trademark bursts of action. Of course Bond would go on to become one of the most iconic literary creations of the 20th century, so any fans of the movies should make a point of picking up this book.

#3. Bringing Down the House – Ben Mezrich

Mezrich’s 2003 tale of MIT students card counting their way to a Blackjack fortune was a best-seller that made everyone think they could beat the system. The book is based on a true story but there is a lot of controversy about what’s fact and what’s fiction. Either way, Mezrich’s vivid writing style makes for an engaging read and the book gives us a glimpse behind the scenes of professional gambling and those who engage in it. Will the team of college kids manage to pull one over on the casino big-wigs and beat the house? This non-fiction book has the rhythm and cadence of a thriller and pulls the reader into the centre of the action on the casino floor.

#4. The Gambler – Dostoevsky

Dostoevsky’s The Gambler is a cautionary tale of addiction and loss at the Roulette table. Widely regarded as one of the greats of 19th century Russian literature, Dostoevsky was himself a gambler and owed his publisher a lot of money. He bet him the publishing rights of all of his past and future works, against money owed, that he could write a book within 30 days. The result was The Gambler – a fascinating insight into mid-19th century casinos and their patrons. Dostoevsky clearly drew on personal experiences when it came to writing this novel, a particularly unlucky trip to the casino providing him with inspiration for what would become one of his signature works.

#5. Tishomingo Blues – Elmore Leonard

Elmore Leonard was famously described by the New Musical Express as “the poet laureate of wild assholes with revolvers”. It was an epithet he loved. Gritty, realistic, and packed with punchy dialogue, Leonard is a writer with style and flair. In Tishomingo Blues, the action is set in a Mississippi casino replete with gangsters, gamblers, and luscious belles. This thriller follows Dennis Lenahan as he navigates dealing with corrupt officialdom and local mafia gangs and tries to stay in one piece. Readers familiar with Leonard’s style will know what to expect from this funny and fast-paced page-turner set in the deepest South.

#6. Casino: Love and Honour in Las Vegas – Nicholas Pileggi

It comes as no surprise to see Pileggi’s true-life tale of Las Vegas mafia Frank ‘Left’ Rosenthal and Tony Spilotro in this list. The Martin Scorsese film Casino, starring Robert De Niro and Joe Pesci, is one of the great gambling films of all time and this is the book that inspired it all. It tells how the Mob basically looted their own casinos in the 1970s and early 1980s. A brutal and fascinating insight into the world of Las Vegas and the Mafia. This is a gripping read for anyone interested in the history of Vegas and the murky side of Sin City.

#7. Beat The Dealer – Edward O. Thorp

Another one for Blackjack lovers. Written by mathematics professor Edward Thorp, Beat The Dealer is basically a guide to card counting. First published in 1962, it outlines the first card counting system and remains relevant today – for those of you blessed with the memory of an elephant. This is the grey area in the casino between science and chance, but it is not actually illegal to practice even though casino pit-bosses tend to frown upon it! Despite the fact that the book is more than 60 years old it still remains relevant to blackjack players in the 21st century.

#8. Roll The Bones: The History of Gambling – David Schwartz

First published in 2006, David Schwartz’s comprehensive history of gambling starts with prehistoric man rolling knucklebones and ends in modern day Las Vegas. On its journey, it includes biblical references to casting of lots, betting in Ancient Rome and Greece, the evolution of playing cards in Medieval China, the birth of the casino in Venice, and the spread of gambling on the back of the British Empire. If you are interested in the roots of Roulette and more, this is the perfect choice.

#9. The Man Who Broke the Bank at Monte Carlo – Robin Quinn

The most recent book in our top ten is The Man Who Broke the Bank at Monte Carlo. It tells the true story of Charles Deville Wells, aka ‘Monte Carlo Wells’, who basically broke the bank – ten times, playing Roulette, in Monte Carlo’s world famous casino. Did he really invent an infallible system? Was he just a fraudster? He certainly ended up becoming Europe’s most wanted man with 36 aliases. It’s a well-researched book and a fascinating read.

#10. Casino Gambling for Dummies – Kevin Blackwood

Easy to read, easy to understand and packed with genuinely useful information – sounds like a winning formula! The Dummies guide to the casino includes guides to all the most popular games, as well as the coolest places to gamble, how to score comps, and the most common gambling mistakes. Many of them delivered in top ten list style (rather like this!). It’s a great guide and essential reading for newbies, while even experienced casino veterans will pick up a thing or two from this tome.