The Crossword Century: 100 Years of Witty Wordplay, Ingenious Puzzles, and Linguistic Mischief

The Crossword Century: 100 Years of Witty Wordplay, Ingenious Puzzles, and Linguistic Mischief

by Alan Connor

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A journalist and word aficionado salutes the 100-year history and pleasures of crossword puzzles
Since its debut in The New York World on December 21, 1913, the crossword puzzle has enjoyed a rich and surprisingly lively existence. Alan Connor, a comic writer known for his exploration of all things crossword in The Guardian, covers…  See more details below


A journalist and word aficionado salutes the 100-year history and pleasures of crossword puzzles
Since its debut in The New York World on December 21, 1913, the crossword puzzle has enjoyed a rich and surprisingly lively existence. Alan Connor, a comic writer known for his exploration of all things crossword in The Guardian, covers every twist and turn: from the 1920s, when crosswords were considered a menace to productive society; to World War II, when they were used to recruit code breakers; to their starring role in a 2008 episode of The Simpsons; and to the continuing influence of people like Will Shortz, the iconic New York Times crossword editor.
He also profiles the colorful characters who make up the interesting and bizarre subculture of crossword constructors and competitive solvers, including a ninety-year-old vicar who still creates devious puzzles for some of the top newspapers, and a man who boasts that he can solve a puzzle in the time it takes to boil an egg.
At a time when the printed word is in decline, Connor marvels at the crossword’s seamless transition onto Kindles and iPads, keeping the puzzle one of America’s favorite pastimes. He also explores the way the human brain processes crosswords versus computers that are largely stumped by clues that require wordplay or a simple grasp of humor.
A fascinating examination of our most beloved linguistic amusement—and filled with tantalizing crosswords and clues embedded in the text—The Crossword Century is sure to attract the attention of the readers who made Word Freak and Just My Type bestsellers.

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Editorial Reviews

Publishers Weekly
The puzzle columnist for the Guardian, Connor celebrates the first 100 years of the ubiquitous black-and-white pencil game with a lighthearted overview. From the crossword’s first appearance in the 1913 New York World to Wordplay, the 2006 documentary about the annual American crossword solving contest, each bite-size chapter covers a different aspect of the pastime with emphasis on 20th-century influences such as from caricaturist Al Hirschfeld, humorist P.G. Wodehouse, and lyricist Stephen Sondheim. The global fever took off in 1924 with publication of the first puzzle collection by a fledgling publishing house now known as Simon & Schuster. While the crossword changes shape from country to country, the passion for solving remains a constant. Connor credits the crossword’s universal popularity to the fact that the inventor didn’t copyright the idea, which would have entailed royalties. Those who resort to looking up answers will especially appreciate Connor’s chapter on cheating, in which he opines, “there’re no Marquess of Queensberry rules” in this arena, so no rules can be broken. Agent: Andrew Gordon, David Higham Associates (UK). (July)

In ways, it is less surprising that crossword puzzles have been around for a full hundred years than that we got along without them for so long before then. There is something especially satisfying about this harmless activity; perhaps it is because, as Stephen Sondheim says, "you know there is a solution." Whatever the case, Guardian crosswords columnist Alan Connor knows that a fine excuse for celebration is here and he has gifted us with a book that pays homage to both these pencil puzzlers and their master constructors and solvers. An artful tribute to a peerless pastime.

From the Publisher
“Alan Connor's Crossword Century is a fun and fascinating tale of language, commerce, culture and play. Before reading this book, I didn't have a clue about the crossword's checkered past. Now I can see its extraordinary future, too.”

John Pollackauthor The Pun Also Rises and Shortcut: How Analogies Reveal Connections, Spark Innovation and Sell Your Greatest Ideas

“If you love language and history and marvel at the genius of puzzles, codes, and game design, Alan Connor's deep dive into the crossword will keep you smiling and eagerly turning pages. Connor playfully explores the history of the beloved, gamified fever dream of sentences, definitions, letters, and words that is the modern crossword and reveals the dance that strange invention has enjoyed with its caretakers across history. If you adore words and wordplay, if you see language as an endless mutating jungle of puzzles and experimentation, you need this book in your life.”

David McRaney, author of You Are Not so Smart and You Are Now Less Dumb

“[Connor offers] something to entertain even the most infrequent dabbler.”

The Financial Times

“As elegantly sprinkled with surprising gems as the most satisfying crossword...thoroughly, consistently entertaining.”

The Sunday Times

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Product Details

Penguin Publishing Group
Publication date:
Sales rank:
Product dimensions:
5.90(w) x 8.30(h) x 1.00(d)
Age Range:
18 Years

Read an Excerpt


This is a book about having FUN with words. And if you’re wondering why that word is in capital letters, all will become clear.

And it’s a very particular form of fun with words: one that involves jumbling and tumbling them into eye-pleasingly symmetrical patterns and making riddles, jokes, and poetry in the form of crossword clues. A love of crosswords is also a love of language—albeit a love that enjoys seeing the object of its affections toyed with, tickled, and flipped upside down.

Crossword puzzles are a silly, playful way of taking English and making it into a game. They have been doing so since December 21, 1913, when the world’s first crossword appeared—although lovers of language had been deriving pleasure from wordplay long before then, of course. However, it was the crossword that came to supersede all other puzzles. It has become a cornerstone of almost all newspapers and, for many, a fondly anticipated daily appointment.

The crossword today looks quite different than that first puzzle—or that should perhaps read “crosswords today” so as to encompass the baroque creations seen in Sunday papers, the strange mutant British form known as the cryptic, and all of the themed and jokey variants on offer on any given day.

What they have in common is the pleasure of identifying what the constructor is asking for and seeing the answers mesh with one another until the puzzle is finished. For a century, the worker has whiled away journeys and parents have passed on tips and tricks in the hope that each grid tackled will be correctly filled.

In The Crossword Century, we’ll be looking at the playfulness, the humor, and the frustration of the crossword in all its forms, and how the world of the puzzle has overlapped with espionage and humor, current affairs and literature. We’ll see fictional crossword encounters, from The West Wing to The Simpsons, and we’ll see crosswords from the real world: the one that seemed to predict the outcome of a presidential election and the ones that appeared to be giving away the secrets of the Second World War.

We’ll look at how clues tantalize those who are addicted to puzzles by sending the solver on wild-goose chases, by being sweetly silly and soberly serious, and by stubbornly withholding their real meanings until the penny drops.

And we ask questions about the experience of solving: Why do some people try to finish crosswords as quickly as possible? Can computers crack clues? And does puzzling really stave off dementia?

As for how to read this book, please feel free to treat it like a puzzle. That is to say, you can start at 1 across and work sequentially, or you can dive in and out and follow your instincts. The chapters are in two sections: The ACROSS entries look at the creation of puzzles and the strange things that can go on within clues and grids, while the DOWNs describe what happens to the crossword once it escapes into the world and meets its solvers.

Like the British man who created the first crossword in New York, we’ll be crossing the Atlantic Ocean—a few times, in fact—and I humbly hope that along the way I might persuade you that the baffling-looking British cryptic is a lot more enjoyable than legend has it.

Are you ready for FUN?


How the crossword first appeared in 1913 and became an overnight sensation in 1924

Newsday’s crossword editor puts it best. “Liverpool’s two greatest gifts to the world of popular culture,” writes Stanley Newman, “are the Beatles and Arthur Wynne.”

The comparison with the Beatles is on the money—or, to use a more British locution, spot-on. Like the music of the Fab Four, the crossword is a global phenomenon that is at once American and British. But while the Beatles are known wherever recorded music is played, Arthur Wynne’s name remains unspoken by almost all. Who was he?

Well, he wasn’t the Lennon or the McCartney of crosswords; we’ll meet them soon enough. He was perhaps crosswords’ Fats Domino: a pioneer who would see his innovation taken by others to strange, often baroque mutant forms and variants.

Not that this was how Wynne saw his career playing out when he became one of the forty million people who emigrated from Europe between 1830 and 1930, and one of the nine million heading from Liverpool for the New World during that same period.

The son of the editor of The Liverpool Mercury, Wynne was—at least initially, and in his own mind—a journalist. He spent most of his newspaper career working for the empire of print mogul William Randolph Hearst. His legacy, though, was not a piece of reporting, and it appeared in the New York World, a Democrat-supporting daily published by Hearst’s rival, Joseph Pulitzer.

As a kind of precursor to the New York Post, The World mixed sensation with investigation, and it was Wynne’s job to add puzzles to the jokes and cartoons for “Fun,” the Sunday magazine section. He had messed around with tried-and-tested formats: word searches, mazes, anagrams, rebuses.

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What People are saying about this

From the Publisher
"There is something to entertain even the most infrequent dabbler"
Financial Times
"Alan Connor's charming, fascinating history . . . is as elegantly sprinkled with surprising gems as the most satisfying crossword . . . thoroughly, consistently entertaining . . . In a single, gloriously decipherable chapter he lays out with perfect clarity the entire range of rules and devices through which cryptic clues work their magic"
Sunday Times

"It is witty, charming, encyclopaedic and highly readable - and it can be read in any order. Take a chapter or a paragraph, a puzzle or a clue. In each the reader will find something to intrigue and delight."

"A lovingly crafted little book, from the table of contents—where chapter titles are hidden in a crossword designed by the great Araucaria—to the index, which skips from 'I give up, see frustration' via 'primness in American crosswords', to finish with 'zookeepers, beleaguered.'"
The Times

"A lovingly crafted little book . . . Connor's wry, good-natured tone and his commitment to the serious business of play make him the perfect guide to a great pastime as it approaches its 100th birthday."
Daily Telegraph

"Connor writes with great flair . . . it is nice to dip in and out of his entertaining essays"
Church Times

"An ideal stocking filler"

"The brilliant new book on crosswords that delivers fun galore whether you're a doer or a duffer"
Mail on Sunday

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