Here are some of my favorite books about games, puzzles, word play, optical illusions, brain teasers and philosophical conundrums, arranged by category. I read a lot of these types of books, and only the best make it onto this list. These are all highly recommended. Buying from these links helps support this website.

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Books on Word Games and Language

Inversions

Scott Kim is a master of ambigrams, using calligraphy to transform nearly any word or phrase into a surprising work of art. Kim creates word art that is symmetrical, recursive, or conveys two messages at once. Words fit inside themselves, fade from figure to ground, and read the same or differently when flipped different ways. Ambigrams have grown in popularity, appearing as corporate logos and even tattoos, but even if you thought you had seen every type of ambigram there is, Inversions may surprise you with a new style you hadn’t thought of. In addition to 58 pages of images, Kim also provides a discourse on the nature of symmetry and a how-to guide for creating ambigrams.

Language on Vacation

Language on Vacation: An Olio of Orthographic Oddities, by Dmitri A. Borgmann, is a 1965 classic. It is currently out of print, but it is well worth purchasing a used copy. Borgmann’s publication of this book led to him being known as the father of logology, a word for recreational linguistics that he coined. The book remains a vibrant introduction to anagrams, palindromes, mirror image words and other forms of word play. Borgmann was the inaugural editor of Word Ways: The Journal of Recreational Linguistics, which is still published today.

Eunoia

Eunoia is a unique book by word-wizard Christian Bök. Each chapter contains only one vowel. Thus, the book is composed entirely of univocalics, words of a single vowel. The letter Y is not used. In addition, each chapter uses parallel syntax and contains certain elements, such as a sea voyage, a banquet, and a “prurient debauch.” Here is how Chapter I begins: “Writing is inhibiting. Sighing, I sit, scribbling in ink this pidgin script. I sing with nihilistic witticism, disciplining signs with trifling gimmicks, impish hijinks which highlight stick sigils. Isn’t it glib? Isn’t it chic? I fit childish insights within rigid limits, writing shtick which might instill priggish misgivings in critics blind with hindsight. I dismiss nitpicking criticism which flirts with philistinism. I bitch. I kibitz – griping whilst criticizing dimwits, sniping whilst indicting nitwits, dismissing simplistic thinking, in which philippic wit is still illicit.”

Oxymoronica

Paradoxically, paradoxical statements often convey a deeper truth, and this is the case with the quotations in Oxymoronica: Paradoxical Wit and Wisdom from History’s Greatest Wordsmiths. This compilation by Mardy Grothe includes sayings both witty and profound, all of which contain some seeming contradiction. Grothe coined the word oxymoronica to describe these quotations, which are like oxymorons that encompass whole statements.

An Introduction to Language

This linguistics textbook conveys not only fascinating information about how language works, but also a love of words and wordplay. An Introduction to Language corrects common misconceptions about language and presents ways of manipulating words for insight and humor.

Parlor Games Books

A Book of Surrealist Games

A Book of Surrealist Games, compiled by Alistair Brotchie and edited by Mel Gooding, is a selection of games played by the Surrealists, including André Breton, Marcel Duchamp, Benjamin Péret and others. The Surrealists led a revolutionary cultural movement and also played a lot of neat games. The book contains images of actual drawings and scorecards created by the Surrealists as they played, and presents the methods of some of the best games. Surrealist games tend to be collaborative and creative, with many non sequiturs and a lot of parallel thinking. The book divides the games into three categories: Language Games, Visual Techniques, and Re-Inventing the World.

Parlor Games

Parlor Games: Amusements and Entertainments for Everyone, edited by Roy Finamore, is a collection of traditional parlor games, including pen and paper games, memory tests, physical action games, riddles and stunts. While many of these games first became popular in the Victorian era, a lot of them are still played today.

Irish Wake Amusements

This fascinating book details the traditional customs regarding wakes in rural Ireland. The Irish saying, “Sing a song at a wake and shed a tear when a child is born,” was followed literally. Along with attending the body of the dead, wakes would include food and drink, singing, storytelling, riddles and games. The author of this book, Seán Ó Súilleabháin, discovered such a lively wake in Co. Mayo in 1921, writing that he had never attended such a wake in his home district of South Kerry. He determined to collect accounts of the games played at wakes throughout Ireland, first publishing Irish Wake Amusements in Irish in 1961 and translating it into English in 1967. The book is both an intriguing glimpse into traditional Irish culture, and a collection of parlor games that may still be enjoyed today.

Books of Philosophical Puzzles

Labyrinths of Reason

Labyrinths of Reason: Paradox, Puzzles and the Frailty of Knowledge, by William Poundstone, is a fascinating philosophical exploration that illustrates some of the most confounding puzzles and paradoxes that humans have wrestled with. This book is packed with stimulating brain teasers and deep philosophical insights. Labyrinths of Reason contains compelling presentations of Newcomb’s Paradox, the Prisoner’s Dilemma, Theseus’ Ship, Hempel’s Raven Paradox, and many other classic puzzles. The book takes the reader through mazes and into alternate universes, using thought experiments to entertain and enlighten.

Metamagical Themas

From 1981 to 1983, Douglas R. Hofstadter wrote a column in Scientific American, a successor to Martin Gardner’s influential column Mathematical Games. Metamagical Themas: Questing for the Essence of Mind and Pattern is a collection of Hofstadter’s columns and other commentary. Hofstadter and his editors allowed him free rein, and his themes range from philosophy to politics to wordplay. Subjects in this 852-page volume include self-referential sentences, a self-modifying game, “innumeracy,” nonsense, game theory, artificial intelligence, and new forms of art.

Thinking, Fast and Slow

Daniel Kahneman, along with Amos Tversky, is one of the primary developers of decision theory, a field that combines mathematics and psychology to examine why people make certain choices. In the course of their research, Kahneman and Tversky invented puzzles such as the Linda Problem, which reveal the cognitive biases behind our mistakes. In Thinking, Fast and Slow, Kahneman discusses his life’s work at length. Telling stories of his discoveries, surprises and missteps, Kahnemean reveals different facets of his central idea: that humans have two systems for thinking. System 1 is quick and intuitive; System 2 is methodical and takes more work. Kahneman explores the many consequences of this, such as the fact that when people are presented with a hard problem (is this stock currently undervalued), they often answer an easier question (do I have good feelings about this company).

The Black Swan

In The Black Swan: The Impact of the Highly Improbable, Nassim Nicholas Taleb explores how our experience does not prepare us for the unexpected. Rather than acknowledge our ignorance, we make meaningless projections. Consider the turkey: over the course of 1,000 days, the turkey has observed that humans provide it with food every day, and it concludes that humans have its best interest at heart and will continue to care for it. On the Wednesday before Thanksgiving, an unexpected event causes the turkey to “incur a revision of belief.” This is an illustration of the problem of induction, which is just one aspect of how a Black Swan event can explode our careful predictions about the future. Taleb, a former Wall Street trader and risk analyst, delights in exposing expert analysis as nonsense.

How Not to Be Wrong

There are so many ways that we can be led astray by our intuition or by misleading numbers, when rigorous logic and careful mathematics can help us arrive at the surprising truth. Jordan Ellenberg’s book, How Not to Be Wrong: The Power of Mathematical Thinking, explains many such situations in entertaining fashion. Described as the Freakonomics of math, Ellenberg’s book is filled with “Aha!” stories, brain teasers that show how math may actually have bearing on real life. The book tackles such questions as why handsome men tend to be jerks, whether you should ever play the lottery, what parts of a military plane should be armored, and why rich individuals vote Republican but rich states vote Democratic.

The Improbability Principle

We all know that the odds of winning the lottery are astronomical. So how unlikely would it be for the same person to win the lottery twice? It is actually quite probable that this will happen to someone (and it has in fact happened to multiple people), due to the law of truly large numbers, one of the ideas mathematician David J. Hand explores in The Improbability Principle: Why Coincidences, Miracles, and Rare Events Happen Every Day. Using real-life examples, Hand illuminates probability principles and cognitive biases such as the law of inevitability, the law of selection, and the law of near enough.

Paradoxes from A to Z

In Paradoxes from A to Z, Michael Clark provides an encyclopedia of the most prominent philosophical paradoxes. This volume examines more than 80 paradoxes, from Achilles to Zeno, in its 245 pages. The style is accessible for the armchair philosopher, with most paradoxes summarized in a page or two. Readers wanting more will appreciate that each paradox has notes on Further Reading, where one can find more in-depth treatments of the subject.

The Pig That Wants to Be Eaten

Ethical dilemmas can be excruciating when you are caught in the middle of them, but fun to puzzle over from afar. Julian Baggini delivers just this sort of fun in The Pig That Wants to Be Eaten: 100 Experiments for the Armchair Philosopher. Baggini borrows from classic problems discussed by philosophers to create short thought experiments. None of these puzzles has a right answer; instead they are entertaining and enlightening food for thought.

Books of Brain Teasers

What Is the Name of This Book?

What Is the Name of This Book?, by Raymond Smullyan, is a collection of more than 200 logic-based brain teasers, compiled by a master puzzler. One of the book’s highlights is the extensive variations on the classic Knights and Knaves puzzles. Smullyan starts out with some easy brain teasers, including the simplest version of the Knights and Knaves. He then keeps adding variations, and combining the variations, allowing readers to work their way up to very complex logic puzzles. There is also a chapter that describes some famous paradoxes and one that discusses aspects of Gödel’s Incompleteness Theorem.

The Big Book of Brain Games

The Big Book of Brain Games, by Ivan Moscovich, is a massive compendium of 1,000 “playthinks,” or mental puzzles of various kinds. The book is divided into chapters like Logic and Probability, Geometry, Perception, and Topology, but the pleasing visual presentation and the sheer size of the volume encourage flipping through at random to see what one might discover.

Hall of Fame Lateral Thinking Puzzles

Lateral thinking puzzles, or as I call them, situation puzzles, are a special type of brain teaser that is meant to be played as a game. A strange situation is presented, with one player aware of the answer that explains what is going on. The other players attempt to find this out by asking yes-or-no questions. Hall of Fame Lateral Thinking Puzzles, by Paul Sloane, is a collection of some of the best situation puzzles. The author has published other collections of varying quality, but this book is highly recommended.

Lewis Carroll’s Games & Puzzles

Lewis Carroll, in addition to writing Alice’s Adventures in Wonderland and Through the Looking-Glass, was a mathematician and inventor of puzzles. Lewis Carroll’s Games & Puzzles, compiled and edited by Edward Wakeling, features 42 of his best, some drawn from the pages of his books and some from letters to friends. They include word games, brain teasers and riddles in verse.

Martin Gardner Books

Martin Gardner, the grandmaster of puzzles, was such a prolific author and editor that he gets a category all his own.

Aha! Gotcha

Aha! Gotcha: Paradoxes to Puzzle and Delight, by Martin Gardner, is one of the most entertaining books by the master of mathematical entertainment. For 25 years, Gardner introduced puzzles to the public through his Mathematical Games column in Scientific American. He also authored or edited more than 100 books. Aha! Gotcha tackles some of philosophy’s most perplexing paradoxes, but in a playful way that can be understood by readers young or old. Each puzzle is presented on a page or two along with a cartoon illustrating it. Gardner divides the puzzles into categories of Logic, Number, Geometry, Probability, Statistics and Time.

Mathematical Puzzles & Diversions

In the December 1956 issue of Scientific American, an article by Martin Gardner appeared, on the subject of hexaflexagons, which started a small craze for the folding paper puzzles. Gardner’s editor asked him if he thought there was enough similar material for a regular feature. Gardner thought so, and he was right. Nearly 300 Mathematical Games columns were published over the next 25 years. Mathematical Puzzles & Diversions is the first collection of these columns, published in 1959. It describes hexaflexagons, Möbius strips, tic-tac-toe variations, the game of Hex, Sam Loyd’s puzzle career, fallacies, brain teasers, card tricks, and why a mirror reverses left and right but not up and down.

New Mathematical Diversions

New Mathematical Diversions from Scientific American is simply the second collection of Martin Gardner’s delightful column, Mathematical Games, from that magazine. For 25 years, Gardner consistently illuminated some of the most thought-provoking puzzles ever discovered. This volume contains columns on Graeco-Latin squares, sphere packing, the four-color map theorem, M.C. Escher, polyominoes, and board games.

My Best Mathematical and Logic Puzzles

This slim volume is Gardner’s own selection of what he considers his best puzzles from collections of the puzzles from his Mathematical Games column, such as Mathematical Puzzles & Diversions above. My Best Mathematical and Logic Puzzles, published by Dover, contains 66 puzzles and answers.

Aha! Insight

Aha! Insight is yet another delightful collection of gems from Mr. Gardner. This book contains brain teasers divided into the categories of Combinatorial, Geometry, Number, Logic, Procedural, and Word puzzles.

 

The Moscow Puzzles

The Moscow Puzzles: 359 Mathematical Recreations is an English translation, edited by Martin Gardner, of the best and most popular puzzle book published in the Soviet Union. This inexpensive Dover book is packed with 309 pages of puzzles, including classic brain teasers, a few simple riddles, and many complex problems that require some serious brain power to figure out. None of the problems require advanced mathematics, but some are quite challenging. As editor, Gardner changed currencies into dollars and cents and units of measurement from the metric system to our own outlandish scheme, but a distinctive Russian essence remains.

Perplexing Puzzles and Tantalizing Teasers

Perplexing Puzzles and Tantalizing Teasers is two Martin Gardner books bound as one, and it is a perfect introduction to brain teasers for kids. The book contains simple riddles, classic brain teasers, and visual puzzles. This Dover volume features mazes, optical illusions, jokes, magic tricks and other fun stuff, as well as puzzles that will make kids use their brains.

The Colossal Book of Short Puzzles and Problems

The Colossal Book of Short Puzzles and Problems, by Martin Garner, contains 494 pages of brain teasers from the realms of wordplay, logic, combinatorics, probability, algebra, geometry, topology, chess and cryptarithms. This is one of Gardner’s more math-heavy collections, so it is a must-have for fans of math-based puzzles, but people who enjoy brain teasers based on logic and wordplay have good puzzles to choose from in this volume as well.

Tribute to a Mathemagician

This qualifies as a Martin Gardner book because it was inspired by him. Tribute to a Mathemagician is a collection of articles that draws from presentations at the fifth Gathering for Gardner, a meeting for mathematicians and puzzle enthusiasts inspired by Gardner’s work. The book contains fascinating puzzles and other mental explorations, which go far deeper than most puzzle books. Fans of word squares will particularly enjoy the article entitled A History of the Ten-Square. Other books in the series include Puzzlers’ Tribute: A Feast for the Mind, based on the first three gatherings, and The Mathemagician and Pied Puzzler, based on the fourth gathering.

Brain Teaser Nonfiction

These books are not collections of brain teasers but works of nonfiction that tell stories of scientific discovery while exploring mental puzzles along the way.

Logicomix: An Epic Search for Truth

Logicomix: An Epic Search for Truth, by Apostolos Doxiadis and others, is a graphic work that tells the story of Bertrand Russell’s philosophical quest, and also the story of the authors telling the story. Along the way, the comic illustrates important philosophical concepts such as Hilbert’s Infinite Hotel, Godel’s Incompleteness Theorem, and the paradox in set theory that Russell discovered, which in one form is known as the Barber Paradox. Many famous philosophers appear in the book, with the messiness of their lives often shown to conflict with their search for logic and truth.

Fermat’s Enigma

Fermat’s Enigma: The Epic Quest to Solve the World’s Greatest Mathematical Problem, by Simon Singh, is a rare type of book: a page-turner about math. Singh tells the story of the centuries-long quest among mathematicians to prove Fermat’s Last Theorem. The subject of the theorem is easy for even non-math whizzes to understand. You are likely familiar with the Pythagorean theorem: a² + b² = c², where c is the hypotenuse of a right triangle. There are infinitely many solutions for a, b and c. Fermat simply stated that for aⁿ + bⁿ = cⁿ, where n is greater than 2, there are no integer solutions for a, b and c. He wrote this in the margin of a book, with the words, “I have discovered a truly marvelous demonstration of this proposition which this margin is too narrow to contain.” If Fermat were not a mathematical genius who was in the habit of challenging his fellow mathematicians, his words might have been thought an empty boast. Instead, it inspired generations of mathematicians to search for a solution.   As Singh tells this surprisingly gripping story, he introduces intriguing puzzles along the way, such as the Truel and the Mutilated Chessboard.

The Code Book

The Code Book: The Science of Secrecy from Ancient Egypt to Quantum Cryptography, by Simon Singh, is a compelling narrative history of cryptography that explains the development of simple Caesar ciphers, the use of the Rosetta Stone to decipher Egyptian heiroglyphics, and many other stories of codes, while posing fascinating mental puzzles along the way. Singh describes points in history when grave matters such as the life of Mary Queen of Scots or the outcome of World War II depended on the strength of secret codes. Singh explains each method of cryptography we encounter as codemakers and codebreakers battle through history. This includes Pretty Good Privacy, the standard for modern email encryption, which relies on the multiplication of large prime numbers, the products of which cannot be factored by existing computers. It also includes a glimpse into the future, where quantum computers may be able to break today’s codes, but quantum cryptography, relying on the vibrations of photons, may create a truly unbreakable code.

Brain Teaser Fiction

Think of a Number

Every mystery novel is a brain teaser of sorts, as the reader joins with the detective in trying to solve the puzzle. Think of a Number by John Verdon has special appeal for puzzle fans, as it involves a serial killer who draws his victims in with a seemingly impossible ability to predict a random number that they think of. The suspense builds as detective Dave Gurney uses deductive reasoning to close in on the killer and uncover his secret.

Books of Optical Illusions

Optical Illusions

If you love optical illusions, then this book is a must-have. Al Seckel’s Optical Illusions: The Science of Visual Perception has more than 300 pages jam-packed with full-color, high-quality illusions, including simple classics and works of art. These optical tricks play with color, depth and movement.

Masters of Deception

In Masters of Deception: Escher, Dalí & the Artists of Optical Illusion, Al Seckel focuses on works by 20 artists who are masters of optical illusions, devoting a chapter to the work of each artist. Dalí and Escher are the most famous names, but there is also a chapter on ambigram master Scott Kim and one on Akiyoshi Kitaoka, creator of stunning color illusions.

Trick Eyes

Akiyoshi Kitaoka is an expert at visual trickery, creating images that deceive our eyes into seeing colors and movement that are not really there. His book, Trick Eyes, is a gallery of some of his most amazing work, as well as a how-to guide. Although Kitaoka’s images can seem impossibly complex, his friendly tone and simplified instructions may inspire you to create your own illusions.

Seeing the Light

Seeing the Light: Optics in Nature, Photography, Color, Vision, and Holography is both a textbook on light and vision and a collection of optical illusions, with detailed information about how they work and how to make them. While the book is filled with technical details, it can also be easily browsed by a layperson seeking to understand illusions.

Books About Games

Brainiac

Ken Jennings’ 74-game winning streak on Jeopardy! in 2004 is the longest in the history of that game show. Jennings embraced the nerd persona and charmed the public with his self-deprecating humor. In Brainiac, Adventures in the Curious, Competitive, Compulsive World of Trivia Buffs, Jennings tells the story of his winning streak, interspersed with explorations into weird corners of quiz bowl culture. The view behind the scenes of Jeopardy! during his run is entertaining, with producers nervously coming to terms with what they had done by — for the first time — allowing champions to keep playing until they were defeated. Jennings also takes us to Stevens Point, Wisconsin, which hosts the world’s largest trivia contest each year, involving 12,000 contestants and 400 teams, and lasting 54 hours.

Word Freak

Stefan Fatsis chronicles his rise through the ranks of competitive Scrabble players, eventually joining the inner circle of expert players, in Word Freak: Heartbreak, Triumph, Genius and Obsession in the World of Competitive Scrabble Players.  Along the way, he tells the fascinating history of Scrabble’s invention, initially sluggish sales, and then sudden explosion of popularity. Fatsis paints portraits of the unusual characters who have the obsessive qualities necessary to be the best at Scrabble, and describes the psychological hold that the game came to have over him. The play-by-play accounts of individual games are surprisingly suspenseful.