Fans pick 100 books like Tricky Business

By Dave Barry,

Here are 100 books that Tricky Business fans have personally recommended if you like Tricky Business. Shepherd is a community of 12,000+ authors and super readers sharing their favorite books with the world.

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Book cover of Tourist Season

Susie Black Author Of Death by Jelly Beans

From my list on funny men whose stories take place in Florida.

Why am I passionate about this?

I am Susie Black. Before I became an award-winning, humorous, cozy mystery author, I had a successful career as a ladies’ swimwear sales exec. As you can imagine, I spent a lot of time in Florida. I interacted with progressive, traditional, and conservative buyers and sellers from large cities to small towns all over the Sunshine State. My experiences gave me a unique perspective on the social mores and hierarchy of Florida’s diverse, multi-layered, and complicated society. 

Susie's book list on funny men whose stories take place in Florida

Susie Black Why did Susie love this book?

As someone who has lived for several decades in a resort area that relies exclusively on tourists to survive, it was no shock that I was all over Carl Hiaasen’s book like white is to rice. I loved how biting humor could shine a light on the dark side of tourism and the impact it had on the locals.

Hiaasen’s debut book is a fast-paced masterpiece that focuses on protecting the Sunshine State from greedy, corrupt characters. I found myself in the unique role of rooting for Eco-terrorists, trying to scare builders away from further developing South Florida by murdering tourists and snowbirds. 

By Carl Hiaasen,

Why should I read it?

3 authors picked Tourist Season as one of their favorite books, and they share why you should read it.

What is this book about?

Take a trip to exotic South Florida with this dark, funny book that established Carl Hiaasen as one of the top mystery writers in the game.

The first sign of trouble is a Shriner's fez washed up on a Miami beach. The next is a suitcase containing the almost-legless body of the local chamber of commerce president found floating in a canal...

The locals are desperate to keep the murders under wraps and the tourist money flowing. But it will take a reporter-turned–private eye to make sense of a caper that mixes football players, politicians, and one very hungry crocodile…


Book cover of Orange Crush

Susie Black Author Of Death by Jelly Beans

From my list on funny men whose stories take place in Florida.

Why am I passionate about this?

I am Susie Black. Before I became an award-winning, humorous, cozy mystery author, I had a successful career as a ladies’ swimwear sales exec. As you can imagine, I spent a lot of time in Florida. I interacted with progressive, traditional, and conservative buyers and sellers from large cities to small towns all over the Sunshine State. My experiences gave me a unique perspective on the social mores and hierarchy of Florida’s diverse, multi-layered, and complicated society. 

Susie's book list on funny men whose stories take place in Florida

Susie Black Why did Susie love this book?

Since I was ten, my parents insisted I watch every major party-political convention. So, it was no surprise that now as an adult political junkie, I devoured every page of this book. I loved the what-ifs the book translated to in today’s political picture.

I marveled at how author Dorsey deftly took the unquestioning tool of the powerful special interests incumbent Florida Governor and transformed him into a candidate with a conscience three weeks before the next election. I gave a standing ovation to Dorsey, who used zippy dialog and a fast-paced plot to hysterically make mincemeat of the hypocritical, holier-than-thou morals of an alley cat displayed by state party officials. 

By Tim Dorsey,

Why should I read it?

1 author picked Orange Crush as one of their favorite books, and they share why you should read it.

What is this book about?

If you like your humour dark and twisty, then you'll love Tim Dorsey's outrageous Serge Storms series of crime novels. The Republicans' "golden boy" and a loyal, unquestioning tool of the powerful special interests handsome, unthreatening, Florida governor-by-default Marlon Conrad seems a virtual shoo-in for re-election. That is, until he undergoes a radical personality shift during a bloody military action in the Balkans. Now it's just three weeks before the election and Marlon is suddenly talking about "issues" and "reform" as he crosses the length and breadth of his home state with an amnesiac speechwriter and a chief of staff…


Book cover of Florida Straits

Susie Black Author Of Death by Jelly Beans

From my list on funny men whose stories take place in Florida.

Why am I passionate about this?

I am Susie Black. Before I became an award-winning, humorous, cozy mystery author, I had a successful career as a ladies’ swimwear sales exec. As you can imagine, I spent a lot of time in Florida. I interacted with progressive, traditional, and conservative buyers and sellers from large cities to small towns all over the Sunshine State. My experiences gave me a unique perspective on the social mores and hierarchy of Florida’s diverse, multi-layered, and complicated society. 

Susie's book list on funny men whose stories take place in Florida

Susie Black Why did Susie love this book?

I’ve always marched to the beat of my own drum, so naturally, a fish-out-of-water coming-of-age laugh-out-loud comedy replete with a zany cast, spot-on dialog, and an unlikely hero had me from page one.

People go to Key West for different reasons…magnificent sunsets, key lime pie, to commune with the ghost of Hemingway…The unlikely hero of this cleverly plotted book went to Key West to become a gangster. I led the cheers and gave him a zillion attaboys for standing up for himself and not allowing anyone to rain on his parade. 

By Laurence Shames,

Why should I read it?

1 author picked Florida Straits as one of their favorite books, and they share why you should read it.

What is this book about?

"People go to Key West for lots of different reasons. Joey Goldman went there to become a gangster..." So begins this classic Key West caper, the hilarious and touching book that launched a much-loved series and introduced the world to Bert the Shirt and his chihuahua Don Giovanni, two of the most unforgettable characters in contemporary fiction. Joey, the illegitimate son of a major NY mafioso, decides to break away from a decidedly unpromising future in the old neighborhood of Queens. But will the old neighborhood and the Family let him go in peace? Not if knucklehead half-brother Gino has…


Book cover of Deep Water

Susie Black Author Of Death by Jelly Beans

From my list on funny men whose stories take place in Florida.

Why am I passionate about this?

I am Susie Black. Before I became an award-winning, humorous, cozy mystery author, I had a successful career as a ladies’ swimwear sales exec. As you can imagine, I spent a lot of time in Florida. I interacted with progressive, traditional, and conservative buyers and sellers from large cities to small towns all over the Sunshine State. My experiences gave me a unique perspective on the social mores and hierarchy of Florida’s diverse, multi-layered, and complicated society. 

Susie's book list on funny men whose stories take place in Florida

Susie Black Why did Susie love this book?

Maybe it’s because, as a woman who worked in a historically male-dominated industry, I always root for the underdog—be it a newbie with the chutzpah to say no to a pushy buyer or a small town fighting off a huge conglomerate. Give me a character who is a caricature of an amusement park scion, dialog dripping with sarcasm, and a zany plot that spits in the eye of corporate America.

I led the applause as S. V. Date gleefully poked fun at the greediness of big business while indicting a state government that, for a price, was more than happy to go along for the ride.

By S.V. Date,

Why should I read it?

1 author picked Deep Water as one of their favorite books, and they share why you should read it.

What is this book about?

A witty satire of planned communities introduces readers to Serenity, Florida--the lifelong dream of amusement park scion Waldo Whipple--a town on the verge of a very public nervous breakdown. 10,000 first printing.


Book cover of Fast Company: How Six Master Gamblers Defy the Odds - and Always Win

Arnold Snyder Author Of Radical Blackjack

From my list on those contemplating gambling as a profession.

Why am I passionate about this?

I was a mailman when I became obsessed with card counting at blackjack. Not having enough money to play at a pro level, I decided to sell a mathematical formula I’d devised for evaluating games and systems. I offered it for sale through gambling newsletters at $100. I immediately had big sales because no one had ever seen a method for estimating card counters’ win rates. I got letters from college math professors asking me how I’d come up with the math. So, I started my own blackjack newsletter where I published my discoveries. I was inducted into the Blackjack Hall of Fame in 2002 and soon had big investors funding my play.

Arnold's book list on those contemplating gambling as a profession

Arnold Snyder Why did Arnold love this book?

Really fun true stories about six gambling legends. Titanic Thompson never entered an official PGA event, yet made more money playing golf than most of the top pros in his era, often by beating the famous pros at their own game. Minnesota Fats never won a major pool tournament, but made so much money traveling from city to city to hustle the local pool sharks he became a legend in the Midwest pool halls. Johnny Moss cut his gambling teeth in illegal poker games in Texas and Oklahoma, then went on to win the first two World Series of Poker championships in 1970 and 1971, winning nine WSOP bracelets in total, his last one in 1988 at the age of 81, making him the oldest WSOP bracelet winner ever.

By Jon Bradshaw,

Why should I read it?

1 author picked Fast Company as one of their favorite books, and they share why you should read it.

What is this book about?

In this classic book, Jon Bradshaw singled out from the world of full-time gamblers six men who consistently win - the men who year after year, deal after deal and proposition after proposition come away with their pockets filled and their sense of infallibility intact.

Bradshaw follows three legendary poker players - Johnny Moss, Pug Pearson, and Titanic Thompson; tennis player Bobby Riggs; pool player Minnesota Fats and backgammon player Tim Holland. His evocation of ambience and his dramatic description of the games themselves are fascinating but Bradshaw also deftly probes their minds and hearts as he attempts to define…


Book cover of Fortune's Formula: The Untold Story of the Scientific Betting System That Beat the Casinos and Wall Street

Barbara Rockefeller Author Of Technical Analysis For Dummies

From my list on for traders using technical analysis.

Why am I passionate about this?

Economics isn't really a good starting point for financial market analysis for the simple reason that its models are wildly inaccurate. As behaviorial economists like Daniel Kahneman have been showing, irrationality and the inability to measure risk properly are a very big component of the investment and trading decisions. But statistical risk management is also sloppy when applied to human behavior because people are not objects that reliably behave the same way under similar circumstances. So when you read an economist about markets or an engineer about risk management, you're missing a lot of the story. In the end, technical analysis is fascinating because how and why humans behave is an enduring mystery.

Barbara's book list on for traders using technical analysis

Barbara Rockefeller Why did Barbara love this book?

The subtitle is The Untold Story of the Scientific Betting System that Beat the Casinos and Wall Street. This book is an easy-to-read narrative of the intersection of the grimy underbelly of betting--with high-minded math. It reminds you that trading is not conducted in a clean little bubble. Technical analysis can give you an edge, but trading is still engaging in battle with opposing forces; strategy and tactics can count as much as building an elegant technical system. 

Your opponent on the trading battlefield will try to trick you, like a general in real warfare. He may keep selling and selling after you have bought, triggering a sell signal in your trading system. He is hunting for your sell signal. The mechanical response is to sell—your system says sell, and you should follow your system. To exit a position when the market goes against you is named a stop,…

By William Poundstone,

Why should I read it?

1 author picked Fortune's Formula as one of their favorite books, and they share why you should read it.

What is this book about?

In 1956, two Bell Labs scientists discovered the scientific formula for getting rich. One was mathematician Claude Shannon, neurotic father of our digital age, whose genius is ranked with Einstein's. The other was John L. Kelly Jr., a Texas-born, gun-toting physicist. Together they applied the science of information theory—the basis of computers and the Internet—to the problem of making as much money as possible, as fast as possible.

Shannon and MIT mathematician Edward O. Thorp took the "Kelly formula" to Las Vegas. It worked. They realized that there was even more money to be made in the stock market. Thorp…


Book cover of Super Casino: Inside the "New" Las Vegas

Mark Bollman Author Of Basic Gambling Mathematics: The Numbers Behind the Neon

From my list on people who challenged Las Vegas.

Why am I passionate about this?

I’ve been playing card games since childhood, and have had a parallel interest in the mathematics behind the games for nearly as long. While I didn’t visit Las Vegas in person until 2000, the stories of how that city was built around the gaming industry quickly came to fascinate me. Digging into the details of the people who have made that city what it is and have come to make their way in the desert has been a fascinating sidelight that has enhanced my recent work writing books on gambling mathematics.

Mark's book list on people who challenged Las Vegas

Mark Bollman Why did Mark love this book?

Many people, including Bill Bennett from Forgotten Man, played big parts in the building, opening, and subsequent operation of the Luxor Casino in Las Vegas. They tell their stories in Super Casino. 

I am a big fan of logistics in general, and found the details of what goes into the Las Vegas casino industry in the 1990s (just before I started visiting Las Vegas and writing about gambling mathematics) to be a fascinating look behind the scenes.

By Pete Earley,

Why should I read it?

1 author picked Super Casino as one of their favorite books, and they share why you should read it.

What is this book about?

Las Vegas was a mob town built on restlessness and hunger, on glitter, greed, and the firm belief that anyone can get lucky once. But in the last decade Las Vegas has had its own change of fortune, transforming itself from a gambler's fun house to one of the country's top family vacation spots. Now Pete Earley--the investigative journalist and award-winning author who stormed Leavenworth in The Hot House--takes us inside today's colossal theme casinos, in a fascinating look at the life, death, and fantastic rebirth of the Las Vegas Strip.

With 320 days of sunshine, 500 churches, 27 golf…


Book cover of The Biggest Game in Town

Jonathan Grotenstein Author Of Ship It Holla Ballas! How a Bunch of 19-Year-Old College Dropouts Used the Internet to Become Poker's Loudest, Craziest, and Richest Crew

From my list on high-stakes poker for people who hate math.

Why am I passionate about this?

As the kid of tournament bridge and Scrabble players, I’ve been hooked on games my whole life. None more so than poker, which has helped me make a living both at the tables and as a writer. I’m currently working on a TV adaptation of Ship It Holla Ballas!  

Jonathan's book list on high-stakes poker for people who hate math

Jonathan Grotenstein Why did Jonathan love this book?

Poker is an American game—maybe the most American game—but an Englishman elevated it into something literary: in 1981, Al Alvarez, a poet, editor, and critic best known for introducing the world to Sylvia Plath and Ted Hughes, traveled to Las Vegas to chronicle the World Series of Poker. His deceptively breezy account of the larger-than-life characters who played a card game for nosebleed stakes inspired a new generation of players to discover the world’s hardest way to make an easy living.

By A. Alvarez,

Why should I read it?

1 author picked The Biggest Game in Town as one of their favorite books, and they share why you should read it.

What is this book about?

Al Alvarez touched down in Las Vegas one hot day in 1981, a dedicated amateur poker player but a stranger to the town and its crazy ways. For three mesmerizing weeks he witnessed some of the monster high-stakes games that could only have happened in Vegas and talked to the extraordinary characters who dominated them--road gamblers and local professionals who won and lost fortunes on a regular basis.

Set over the course of one tournament, The Biggest Game in Town is botha chronicle of the World Series of Poker--the first ever written--and a portrait of the hustlers, madmen, and geniuses…


Book cover of The Noble Hustle: Poker, Beef Jerky and Death

Jonathan Grotenstein Author Of Ship It Holla Ballas! How a Bunch of 19-Year-Old College Dropouts Used the Internet to Become Poker's Loudest, Craziest, and Richest Crew

From my list on high-stakes poker for people who hate math.

Why am I passionate about this?

As the kid of tournament bridge and Scrabble players, I’ve been hooked on games my whole life. None more so than poker, which has helped me make a living both at the tables and as a writer. I’m currently working on a TV adaptation of Ship It Holla Ballas!  

Jonathan's book list on high-stakes poker for people who hate math

Jonathan Grotenstein Why did Jonathan love this book?

In a self-conscious effort to re-enact Positively Fifth Street’s reimagining of the writer’s journey, Grantland Magazine assigned Colson Whitehead to cover the 2011 World Series in exchange for the $10,000 entry fee. He falls short of matching McManus’ success on the felt, but that’s not really the point: the meat is in the interaction between the poker and Whitehead’s struggle with depression. Which might be unbearable in the hands of anyone other than Colson Whitehead, maybe the best there is at crafting sentences that will make you laugh and wince at the same time.

By Colson Whitehead,

Why should I read it?

1 author picked The Noble Hustle as one of their favorite books, and they share why you should read it.

What is this book about?

From the two-time Pulitzer Prize-winning author of The Underground Railroad and The Nickel Boys • “Whitehead proves a brilliant sociologist of the poker world.” —The Boston Globe

In 2011, Grantland magazine gave bestselling novelist Colson Whitehead $10,000 to play at the World Series of Poker in Las Vegas. It was the assignment of a lifetime, except for one hitch—he’d never played in a casino tournament before. With just six weeks to train, our humble narrator took the Greyhound to Atlantic City to learn the ways of high-stakes Texas Hold’em.

Poker culture, he discovered, is marked by joy, heartbreak, and grizzled…


Book cover of Bob the Gambler

Cara Bertoia Author Of Casino Queen

From my list on true stories set in the casino industry.

Why am I passionate about this?

Growing up in a strait-laced Southern family, I was always fascinated with casinos. In my twenties on a summer hiatus from teaching in North Carolina, I drove to California and became a dealer at Caesars in Lake Tahoe. My mother highly disapproved of my working in a casino, "a place so bad it has 'sin' in the middle." Eventually, I returned east to take a hi-tech job in Boston. I also began working on my MFA in writing at Emerson. My characters were breathed into life from my years in the gambling industry. You learn a lot about the human personality when you watch thousands of people from behind the felt of a blackjack table.

Cara's book list on true stories set in the casino industry

Cara Bertoia Why did Cara love this book?

This is a novel based on Frederick’s own gambling addiction on the Mississippi riverboats. Ray and Jewel Kaiser love to gamble, until a fun night out becomes a compulsion. They find themselves showing up at the Paradise casino all hours of the day and night, becoming intimate with the employees and escalating their bets. After visiting the area, I knew the scenes in the casino ring true and the dialogue is so on point, that you root for Ray and Jewel even though in the back of your mind you know the house always wins. 

By Frederick Barthelme,

Why should I read it?

1 author picked Bob the Gambler as one of their favorite books, and they share why you should read it.

What is this book about?

A New York Times Notable Book In this darkly funny story, Ray and Jewel Kaiser try (and push) their luck at the Paradise casino. Peopled with dazed denizens, body-pierced children, a lusty grocery-store manager, and hourly employees in full revolt, this is a novel about wising up sooner rather than later--"a wise and funny tale" (New York Times Book Review) that is "masterfully observed" (John Barth).


Book cover of Tourist Season
Book cover of Orange Crush
Book cover of Florida Straits

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Interested in gambling, maritime, and Florida?

Gambling 42 books
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Florida 140 books