Thinking Inside the Box: Adventures with Crosswords and the Puzzling People Who Can't Live Without Them

Thinking Inside the Box: Adventures with Crosswords and the Puzzling People Who Can't Live Without Them

by Adrienne Raphel


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A delightful, erudite, and immersive exploration of the crossword puzzle and its fascinating history by a brilliant young writer

Almost as soon as it appeared, the crossword puzzle had already become indispensable to our lives. Invented practically by accident in 1913, when a newspaper editor at the New York World was casting around for something to fill empty column space, it became a roaring commercial success practically overnight. Ever since then, the humble puzzle—consisting of a grid of blank squares in which solvers write answers in response to clues—has been an essential ingredient of any newspaper worth its salt. The puzzle's daily devotees include everyone from subway riders looking to pass the time to cultural icons such as Martha Stewart, Bill Clinton, and Yo-Yo Ma. Today, its popularity is greater than ever, even as the media world has undergone a perilous digital transformation. But why, exactly, are the crossword's satisfactions so sweet that it is a fixture of breakfast tables, nightstands, and commutes, and has even given rise to competitive crossword tournaments? There are mysteries beyond the clues.

Blending first-person reporting from the world of crosswords with a delightful telling of its rich literary history, Adrienne Raphel dives into the secrets of this classic pastime. At the annual American Crossword Puzzle Tournament, she rubs shoulders with elite solvers of the world; aboard a crossword- themed cruise, she picks the brains of the enthusiasts whose idea of a good time is a week on the high seas with nothing but crosswords to do; and, visiting the home and office of Will Shortz, New York Times crossword editor and NPR's official "Puzzlemaster," she goes behind the scenes to see for herself how America''s gold standard of puzzles is made.

As ingenious as it is fun, Thinking Inside the Box is a love letter not just to the abiding power of the crossword but to the infinite joys and playful possibilities of language itself. This book will be a treat for die-hard cruciverbalists and first-time solvers alike.

Product Details

ISBN-13: 9780525522089
Publisher: Penguin Publishing Group
Publication date: 03/17/2020
Pages: 304
Sales rank: 56,548
Product dimensions: 6.00(w) x 9.00(h) x 1.30(d)

About the Author

Adrienne Raphel has written for The New Yorker, The Atlantic, The New Republic, Slate, and Poetry, among other publications. Her debut poetry collection, What Was It For, won the Rescue Press Black Box Poetry Prize. Born in southern New Jersey and raised in northern Vermont, she holds an MFA from the Iowa Writers' Workshop and a PhD from Harvard.

Read an Excerpt



FUN: Arthur Wynne,

Margaret Petherbridge Farrar, and the Origins of the Puzzle


The story of the crossword begins with the birth of Arthur Wynne on June 22, 1891, in Liverpool, England, where his father was the editor of the local Liverpool Mercury. When Wynne was nineteen, he emigrated to Pittsburgh, where he took a job on the Pittsburgh Press and played violin in the city's symphony orchestra. Soon, Wynne moved to New York and joined the staff of the New York World.


The World had launched in New York City in 1860. Each issue cost a penny. In 1864, the paper's editor published forged reports supposedly from President Abraham Lincoln that urged men to join the Union army. Lincoln was furious, the editor was arrested, and the World shut down for several days. The paper limped along printing propaganda for its various owners until 1883, when famed publisher Joseph Pulitzer bought the operation. In an aggressive circulation-boosting campaign, Pulitzer pumped the paper full of pulpy news and yellow journalism, transforming the World into one of the most popular publications in the country and the first in America to reach over one million subscribers daily. Pulitzer hired blockbuster reporters like Nellie Bly, who performed such gonzo stunts as traveling, for the World, around the world in seventy-two days, just to best Phileas Fogg's famous eighty. In 1890, operations moved into a brand-new, eighteen-story, gold-domed skyscraper next to City Hall on Park Row at the bottom tip of Manhattan, making the World's home the world's then-tallest office building. In 1911, the paper launched its weekly color supplement: FUN.


By 1913, Arthur Wynne had been put in charge of FUN. For that year's Christmas edition, set to run on Sunday, December 21, Wynne was in a jam: he had to fill space but had nothing to fill it with. He'd been instructed to add more puzzles to FUN, and Wynne, in desperation, turned his writer's block into a grid, a diamond-shaped interlocking set of squares flanked by clues that ran differently across and down. "FUN's Word-Cross Puzzle" instructed readers, "Fill in the small squares with words which agree with the following definitions." The crossword conceit-here are clues, here is a grid, go forth and fill the grid with the answers to these clues-was born.


Wynne's Word-Cross looks like a modern crossword, with obvious differences. It's a diamond, not a square, and rather than black spaces throughout, there's one concentrated blank in the middle, like a doughnut hole. Rather than separating the clues into Across and Down, Wynne listed clues by giving their beginning and ending squares.


Wynne's puzzle doesn't deploy pyrotechnic layers of wordplay. The clues proceed as fairly straightforward definitions; none of them ask the reader to solve a riddle, or decode an acrostic, or undo a pun to arrive at the solution. Ambiguity is on the level of information rather than imagination: "A bird" (DOVE), for example, could have any number of solutions, but this puzzle is looking only for flying animals, not, say, jailbirds or stool pigeons. Most clues are fairly generic. Many of the clues establish a bond between the clue writer and the solver, a wink from Wynne to us: "What we should all be," for example (MORAL), or, "What this puzzle is" (HARD). The puzzle also repeats itself: "A pigeon," like "A bird," is also DOVE. Some require extremely esoteric knowledge-"The fibre of the gomuti palm" (DOH) would likely be impossible for most nonbotanists, particularly since the gomuti is far more common in Indonesia than Manhattan-so filling in the puzzle relies not only on the reader's capacity to get the clues via the definitions alone but on the simultaneous ability to deduce the answer from corresponding letters in the grid.


FUN and the origin myth of Wynne's invention notwithstanding, part of the ingenuity of Wynne's Word-Cross is that it isn't original at all. Wynne's genius wasn't to reinvent the wheel, but to move the needle precisely enough so that his new game would excite but not befuddle solvers. Victorian newspapers and magazines frequently featured word squares that challenged readers to fill in blanks with words that read the same horizontally and vertically; a simple example might be the following:


                O             F              F


                F              O             E


                F              E              D


Wynne freely acknowledged that his word-cross did not come to him sui generis. He'd based the puzzle on similar word puzzles that had been published in children's newspapers in England. The popular children's magazine St. Nicholas had regularly been publishing acrostics and word puzzles since 1873. Its "Riddle Box" featured games such as a "cross-word enigma," a riddle that asks readers to tease out a word from a rhyming poem of cryptic clues. Other magazines had also started to print word-grid games. The September 1904 edition of the People's Home Journal featured a blended square, or five word squares that interlocked at the corners. The blank grid wasn't printed, though, meaning that solvers had to draw the squares for themselves to fill it in. And proto-crosswords weren't only in English. In 1890, Italian journalist Giuseppe Airoldi introduced a four-by-four word game printed with a grid.


But Wynne's crossword was the first that incorporated crossed words directly on the page with blocked-out squares, pushing beyond the natural limitations of the word square and creating a much more flexible, and expandable, game. Wynne took advantage of advances in twentieth-century printing technology that made it easier to print large grids in the newspaper itself. Rather than posing a problem and asking readers to draw their own grids or write the answers elsewhere, Wynne's puzzle provides the empty squares, inviting the reader to engage with the puzzle right in the newspaper. Wynne also introduced black squares into his symmetrical rows and columns, which gave the puzzles clear units of negative space and allowed for more varied grids. If music comes to life in the spaces between the notes, the crossword became the crossword because of the gaps in the puzzle.


Each week, Wynne printed a new puzzle of this word-crossed type in the World. A typographical error two weeks after Wynne's original Word-Cross transposed the title's two words, suggesting that readers "Find the Missing Cross Words," and the following week, the paper presented the puzzle under the heading "Fun's Cross-Word Puzzle." Eventually, the hyphen disappeared, as did the capital letters, and the Cross-Word became the crossword. The trend of disappearing hyphens isn't unique to the crossword; the early twentieth century saw many words that were once hyphenated become either two separate words or closed compounds (to-day, ice-cream, bumble-bee). Cross-Word, like Xerox or Band-Aid, shifted from becoming descriptive of a certain kind of word game in one particular paper to the generic name for the puzzle itself.


Jokes, riddles, comics, rebuses, advertisements, and other layers of subcutaneous information insulated FUN from the rest of the World. (A full-page ad in January 1914 proclaims, LET US MAKE YOU FAT. By March, another advertisement, in exactly the same location, declared that FAT IS DANGEROUS.) Readers soon began to submit their own crossword puzzles to the paper. The grids were usually diamonds but erratic in size and shape. No black squares interrupted the white squares, as is typical in crosswords today. Mostly, these puzzles used diamond-shaped grids, but the shapes were not standardized: in January 1915, for example, one week's grid was in the shape of an F; the next week, a U; and the following week, an N. "That spells FUN for every one of FUN's puzzle solvers," wrote Wynne.


Wynne's first Word-Cross already had one answer filled in-FUN-so that even readers who did not go to the trouble of filling out the rest of the grid would be cued that this was a FUN activity. The brand added another ritual dimension to the nature of solving. Crossworders were, from the beginning, social. You filled in the same grid with your remote fellow crew, week after week. Already in 1915, Wynne imagined his readers as a loyal coterie, turning to FUN religiously each Sunday to fill in the same grid with your cohort members far and wide. Once you were a crossworder, you were in the club.


Wynne tried to patent the crossword, but the World refused to foot this bill, and the crossword remained open for all to use. In 1920, it cost thirty-five dollars to file and issue a patent, and a typical patent lawyer's fee would have been about seventy dollars.





Wynne's invention of desperation became an institution overnight.


After constructing the paper's first seven crosswords himself, Wynne slyly suggested to World readers that it was more difficult to create a crossword than to solve one. Like Tom Sawyer's friends eagerly picking up the pail of whitewash to join the "fun" and paint the fence, Wynne's readers took the bait and started doing his work for him. In February 1914, a Mrs. M. B. Wood became the first constructor to be given a byline. By the following year, Wynne's trick had worked too well. In a headnote to the puzzle of March 7, 1915, Wynne painted a vivid picture of the deluge at his office: "Everywhere your eyes rest on boxes, barrels and crates, each one filled with cross-word puzzles patiently awaiting publication," he wrote. He begged readers to curb their zeal: "The puzzle editor has kindly figured out that the present supply will last until the second week in December, 2100." Current crossword editors face the same problem. Will Shortz at the New York Times typically has a backlog of at least three to four months. Though topical puzzles can be pushed through more quickly, for evergreens, or themes that aren't pegged to a particular news cycle, puzzle gestation can take as long as human gestation. (In 2018, one constructor told me that he knew he had a puzzle coming out that year around Halloween. It was March.)


Wynne was getting sick of the crossword. He became a careless editor, regularly publishing puzzles riddled with errors. Angry solvers wrote into the paper in droves, badgering Wynne about clues that didn't match their definitions, misspellings baked into the grid, or answers that led to nowhere. And yet the crossword was more popular than ever. Every Sunday's World contained several sidebars scattered throughout the sections instructing readers to look for the crossword in FUN, less a reminder about the puzzle's existence-after all, the puzzle had long been established as a staple of Sunday's FUN-than a promotional teaser for one of the paper's most popular features. Readers grumbled at poorly constructed puzzles, but they exploded on the occasional weeks that FUN didn't publish a crossword at all: "The only thing I give a hang about on your page or in your Sunday magazine is the crossword," wrote one solver.


By 1921, the crossword had outgrown Wynne, and Wynne, desperate to rid himself of the albatross, turned to John O'Hara Cosgrave, the World's executive editor, for help. Cosgrave had no more time or interest than Wynne in devoting his days to placating vociferous cruciverbalists (that is, people skilled in solving or creating crosswords, from Latin cruci-, "cross," plus verbum, "word"). But he did have one asset Wynne lacked: a new secretary.





Margaret Petherbridge was born in 1897 in Brooklyn, New York, where her father owned a licorice factory. She attended the Berkeley Institute in Park Slope, one of the oldest and most highly regarded independent schools in New York, where seniors routinely received automatic entry into the top women's colleges. Though most of Brooklyn was still farmland, Park Slope had established itself as a genteel residential neighborhood with easy access into Manhattan, and Petherbridge's classmates hailed from the borough's socioeconomic crème de la crème. A Berkeley girl's schedule followed the so-called Vassar model: academics from nine to noon, home for luncheon, then physical education in the afternoon. After attending Berkeley, Petherbridge graduated from Smith College in 1919, then returned to New York, where, with the help of a roommate's stepfather, she landed a job in 1921 as secretary to the executive editor of the New York World.


An aspiring journalist, Petherbridge hoped that working for Cosgrave would provide her foray into writing for the World. So when Cosgrave assigned Petherbridge to help Wynne with the crossword, Petherbridge was less than thrilled. She, like many of the people in her office, saw the crossword as undecorative filler, schlocky drivel to puff out the paper and placate the masses.


With her career stalled in crossword Siberia, Petherbridge devoted as little time as possible to the puzzle. She'd never done a crossword before, and she wasn't about to start now. Rather than bothering to test the puzzles that readers submitted to the paper, she selected grids based solely on aesthetic appeal and waved them untouched to the typesetters, just as a bored high school student might create fill-in-the-blank bubble-grid patterns in her standardized test booklets. Readers continued to complain, but Petherbridge brushed aside their concerns as "the work of cranks."


The stalemate between miffed readers and diffident editor might have persisted for years, if not for a hiring coup and a quirk of intraoffice geography. In 1922, the World poached legendary columnist Franklin Pierce Adams-"F.P.A.," as he signed his work-from the rival New-York Tribune. A feature in F.P.A.'s most famous column, "The Conning Tower," launched the careers of writers such as Dorothy Parker, Moss Hart, George S. Kaufman, and Edna St. Vincent Millay. F.P.A. was also an avid cruciverbalist, and the World happened to install him in an office next to Petherbridge's. Until recently, Sunday's FUN insert had reliably brought F.P.A. a weekly dose of immense pleasure. Now, F.P.A. could unleash his irritation at the puzzle's decline to the source. Hardly known for his demure manner, F.P.A. marched into Petherbridge's office every Monday morning and chewed her out, clue by poorly constructed clue. Petherbridge ignored F.P.A. at first, but the "comma-hunter of Park Row" harangued Petherbridge week after week, and finally she consented to at least try solving one of these things.


The cranks were right. Under her supposed watch, the puzzle, she discovered, was a mess: clues left out, wrong numbering, warped definitions, and words, she said, "that had no right to be dragged out of their native obscurity." Petherbridge was mortified, but she also saw an opportunity. If personages as esteemed in the world of letters as Franklin Pierce Adams were poring over the crossword week after week, the puzzle might be her opportunity. Everyone who was anyone, it seemed, was addicted to the thing, and what had seemed like a major nuisance could be her chance to make her mark. Like an architect renovating a house that has great bones but has fallen into disrepair, Petherbridge realized that fixing the crossword puzzle could be her ticket to a career after all-but it was going to take some doing.

Table of Contents

Introduction xi

1 FUN: Arthur Wynne, Margaret Petherbridge Farrar, and the Origins of the Puzzle 1

2 The Cross Word Puzzle Book and the Crossword Craze 15

3 How to Construct a Crossword 33

4 Pleasantville, New York: Will Shortz 61

5 The Crossword Hyacinth: England and the Cryptic Crossword 77

6 World War II and the Gray Lady 89

7 The Oreo War: Race, Gender, and the Puzzle 101

8 Krossvords and Mots Croisés 121

9 Tournament of Champions 133

10 Decoding the Crossword 167

11 This Is Not a Crossword 187

12 Crosswords and the Media: The Crossword in the Digital Age 203

13 The Hardest Crossword 219

Epilogue: A Crossword Crossing 231

Afterword 247

Acknowledgments 249

Notes 255

Image credits 271

Index 273

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