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Thinking Inside the Box: Adventures with Crosswords and the Puzzling People Who Can't Live Without Them Hardcover – March 17, 2020
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A delightful, erudite, and immersive exploration of the crossword puzzle and its fascinating history
Almost as soon as it appeared, the crossword puzzle became 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 almost overnight. Ever since then, the humble puzzle has been an essential ingredient of any newspaper worth its salt. But why, exactly, are the crossword’s satisfactions so sweet?
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. Thinking Inside the Box is an ingenious love letter not just to the abiding power of the crossword but to the infinite joys and playful possibilities of language itself.
- Print length304 pages
- LanguageEnglish
- PublisherPenguin Press
- Publication dateMarch 17, 2020
- Dimensions6.22 x 1 x 9.27 inches
- ISBN-100525522085
- ISBN-13978-0525522089
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Editorial Reviews
Review
"Raphel proves a skilled cultural historian, dipping into newspaper archives and movie reels and private correspondence to describe how the crossword came to conquer the world. . . . In my favorite memoir chapter, Raphel visits a writing retreat to construct her own crossword. After much technical discussion of grids and themes and fill, she writes: 'I became a mechanical god. I shifted gears; I tuned each letter individually. … I was a chemist, titrating my micro-universe; a lepidopterist, shifting a butterfly’s wing onto a pin.' She was also, in this and only this, a failure. Her puzzle was rejected, as so many are, by The Times. But her affectionate exegesis of this pastime, this passion, this 'temporary madness,' succeeds. Like a good crossword, her book challenges us to back away from our assumptions, allows us to think differently and apply ourselves again." — Peter Sagal, New York Times Book Review
“Fascinating . . . Raphel is particularly good at shifting viewpoints. . . . Chapters, such as ‘This Is Not a Crossword,’ looking at the intersection between surrealism and crosswords, fairly sing… Raphel’s approach is reminiscent of Mary Roach’s work, and even cruciverbalists well versed in their hobby’s history will discover something illuminating here. Nonpuzzling readers may discover a new hobby.” — Library Journal
“Raphel delivers an intriguing and informative look at the crossword puzzle. . . This enjoyable survey illuminates many lesser-known aspects of a wildly popular pastime.” — Publishers Weekly
“For crossword puzzlers of every ilk, from solvers of the Monday-edition no-brainer to pencil-chewing addicts of the cryptic, Thinking Inside The Box is a gold mine of revelations. If there is a pantheon of cruciverbalist scholars, Adrienne Raphel has established herself squarely within it.” – Mary Norris, bestselling author of Between You & Me: Confessions of a Comma Queen and Greek to Me: Adventures of the Comma Queen
“Thinking Inside the Box is a witty, wise, and wonderfully weird journey that will change the way you think. Raphel is an insatiably curious and infectiously passionate guide who plunges headfirst into the rich world of puzzles and the people who love them to reveal the fascinating acrobatics of language and the inner life of words. This book is a delight.” – Bianca Bosker, bestselling author of Cork Dork: A Wine-Fueled Adventure Among the Obsessive Sommeliers, Big Bottle Hunters, and Rogue Scientists Who Taught Me to Live for Taste
“If you remember precisely where you were when you first encountered the words ETUI and ONER, I suspect you’ll be enchanted by Adrienne Raphel’s Thinking Inside the Box. This delightfully engrossing, charmingly and enthusiastically well-written history of the crossword puzzle tells you everything you need to know, and any number of things you couldn’t have imagined, about the invention and eventual world domination of the thing that daily scratches a particular human itch: ‘the yearning to solve a riddle, the desire to fill in a blank space, the obsession with perfection.’” – Benjamin Dreyer, bestselling author of Dreyer's English: An Utterly Correct Guide to Clarity and Style
“Thinking Inside the Box, like the puzzles it elegantly features, is full of treasures, surprises and fun. Adrienne takes readers from Will Shortz's empire hub in Pleasantville, NY, to the pages of Vladimir Nabokov's crossword butterfly puzzle doodles, to the blistering hotel ballrooms of crossword competitions, richly bringing to life the quirky, obsessive, fascinating characters in the crossword world. You'll never think about filling in the squares the same way again.” – Mary Pilon, bestselling author of The Monopolists: Obsession, Fury, and the Scandal Behind the World's Favorite Board Game and The Kevin Show: An Olympic Athlete’s Battle with Mental Illness
“Who would ever have thought the innocent crossword would hide such an intriguing story! After reading Adrienne Raphel's beautifully researched account, full of humor and personal insight, I've come to see these puzzles in a new light, and I certainly now treat their creators with fresh respect.” – Professor David Crystal, author of The Cambridge Encyclopedia of the English Language
About the Author
Excerpt. © Reprinted by permission. All rights reserved.
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 crme de la crme. 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.
Product details
- Publisher : Penguin Press; First Edition (March 17, 2020)
- Language : English
- Hardcover : 304 pages
- ISBN-10 : 0525522085
- ISBN-13 : 978-0525522089
- Item Weight : 1.13 pounds
- Dimensions : 6.22 x 1 x 9.27 inches
- Best Sellers Rank: #96,590 in Books (See Top 100 in Books)
- #216 in Communication & Media Studies
- #226 in Crossword Puzzles (Books)
- #964 in Words, Language & Grammar (Books)
- Customer Reviews:
About the author

Adrienne Raphel is the author of Thinking Inside the Box: Adventures with Crosswords and the Puzzling People Who Can't Live Without Them (Penguin Press, 2020), and What Was It For (Rescue Press, 2017). Her essays, poetry, and criticism appear in The New Yorker, Poetry, The New Republic, The Atlantic, Paris Review Daily, Slate, Lana Turner Journal, Poets & Writers, The Iowa Review, and other publications.
Born in New Jersey and raised in Vermont, Raphel holds a PhD in English from Harvard University, an MFA in poetry from the Iowa Writers' Workshop, and an AB (summa cum laude) from Princeton University. She is currently a Lecturer in the Princeton Writing Program.
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I decided a great way to an “A” would be to construct a crossword puzzle using primarily words from the Earth Science textbook. After all, the prof wrote it, how could he not be impressed? Turns out easier said than done! Selecting words for length and letter combinations, construction of the 15x15 square with the black sections laid out in appropriate symmetrical fashion was a far more difficult and time consuming task than I anticipated but I kept plugging.
Finally, turned in a document labeled “Earth Sciences Crossword” – down and across clues, blank puzzle with the black squares and word squares and one fully filled in with the answers, as well as a cross reference to the text where the specific word came from.
I was called to the professor’s office the next week. “What is this?” he asked, “I have never seen anything like it.” Turns out that since he recently moved to the U.S. from Iran, he had never done one! Once I explained how it worked, what it meant and what was involved in the design he seemed impressed by the amount of work, if not the end product.
Don’t think I got the A, but the book “Thinking Inside the Box” caught my attention and got me thinking of those days. The book is an interesting diversion into all things crossword – history, construction (computers do a lot of heavy lifting these days), competitions, roles of press, etc. so for the crossword nut, this book is a fascinating journey. For regular folks, maybe not so much. My relationship with crosswords these days tend to be doing the daily “Mini” published by the NY Times – quick and easy, entertaining and not too taxing.
The book is well researched and written and entertaining if you have ever had a curious streak about the great pastime of playing with words.
As a devoted consumer of The New York Times' daily crossword I found the sections of Raphel's book that dealt specifically with it to be the most enjoyable. Her visit with Will Shortz and his team of editors confirmed my opinion of them as pleasant, erudite, and friendly folks, and I enjoyed her account of how the Gray Lady came to publish crossword puzzles and how those puzzles were influenced by the personalities of such former editors as Margaret Farrar and Eugene Maleska. It was also interesting to learn the early history of crosswords and to read more about the British style cryptic crossword, examples of which I have made attempts to solve but without much success. I'm an Anglophile but I can't seem to wrap my head around British puzzles for some reason. I found Raphel's chapter on creating her own crossword puzzle to be slightly overwrought in places, and some of her investigations into more outre versions of the crossword, like those based on Magritte's "This is Not a Pipe" were more mystifying than illuminating. And while I'm sure the Crossword Cruise on the Queen Mary 2 was enjoyable, I'm not sure it deserved quite so much space.
But these are mere quibbles and probably specific only to me, so whether you are a crossword fanatic, an occasional solver, or interested but have not yet taken the plunge, you'll find a lot to enjoy in Thinking Inside The Box.
The book is a quick and easy read, I will look for other books by the author and I do recommend it.











