Crosswords history animates Anna Shechtman’s ‘Riddles of the Sphinx’

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Word games are knotty, paradoxical devices. They offer players the illusion of control: What could be tidier than a Scrabble board, or the orderly grid of a crossword puzzle? But they are possible only because language is untamable, flush with connotations and insinuations that we cannot hope to systematize.

No one knows this better than Anna Shechtman, who confronts the waywardness of words both in her capacity as a literature professor at Cornell University and as a contributor of crosswords to the New Yorker. Shechtman was a precocious constructor, as authors of crosswords are called (at least when they are not called, somewhat grandiosely, cruciverbalists); her puzzles were first published in the New York Times when she was in college. After she graduated, she secured a job as assistant to Will Shortz, the paper’s longtime crosswords editor, and it was in his employ that she began to reflect on the political implications of the seemingly innocuous games she designed and tweaked each day. Crossword clues are supposed to draw on “common knowledge,” but who are the proprietors of this mystical article? Is there any such thing? And perhaps most important, can constructors neutralize the chaos of language, with its mad tumult of jostling meanings? Should they even try?

These are some of the questions Shechtman poses in “The Riddles of the Sphinx,” a book too mischievously multiform to classify. It is in part a history of the crossword puzzle, which was invented by Arthur Wynne in 1913 and quickly denigrated as a frivolously feminine pursuit. The press delighted in framing the crossword craze that erupted in the 1920s as a “vice,” sometimes even an addiction. Columnists and commentators went so far as to worry that the puzzle was a “threat to the family unit,” as Shechtman writes: Women suspected of contracting “crossword puzzleitis” were accused of neglecting their household duties to riffle through their dictionaries.

For the affluent White women who dominated the field in its first decades of existence, however, crosswords were more than an engrossing distraction. “Writing puzzles offered three unique satisfactions,” Shechtman explains. It afforded the women she surveys throughout the book “a job in journalism, a profession that might otherwise exclude them; a political tool with which to shape the canon of ‘common knowledge’; and, perhaps above all, a coping mechanism for a life under patriarchy.”

For first-wave feminists like Ruth Hale (1887-1934), crosswords were an escape into a domain in which women might exercise some authority for once (indeed, Hale is responsible for formally codifying the rules by which puzzle constructors abide to this day). For traditionalists like Margaret Farrar (1897-1984), the first crossword editor at the New York Times, writing puzzles was work that masqueraded as leisure — and that therefore allowed her to think of herself as a housewife even as she hunched over the grid. (Farrar, who once remarked that the crossword is “as old as the Sphinx … and as fatal in its fascination,” gives the book its title.) And for radicals like Julia Penelope (1941-2013), an erstwhile lesbian separatist who ended up alienating most of her closest allies, crosswords were an occasion to overhaul a language that had been irrevocably tainted by misogynistic associations.

Associations, it emerges, are the currency of crosswords — the cleverest clues are dense with puns, word play and sly allusions — and they are also the currency of Shechtman’s witty and rewarding book. She relates her fascination with puzzles to her love of modernist authors like James Joyce and Samuel Beckett, who unsettled language by calling attention to its formal qualities in much the same way that the best constructors can, and she allows herself unrepentantly cerebral essayettes on topics ranging from the cantankerous fiction writer and crossword aficionado Jean Stafford to Freudian psychoanalysis — subjects that could prove unapproachably academic in the wrong hands but become fresh fascinations in Shechtman’s.

She even proposes that there is a parallel between her propensity for puzzle-making and her severe anorexia as a teenager and young adult, a connection that she concedes “will strike most people as tenuous or arbitrary.” But by the end of “The Riddles of the Sphinx,” the comparison makes good sense. Whether she was counting calories or organizing words into clean squares in her notebook, Shechtman felt that she was “mastering forms that should be unmasterable,” establishing the dominance of mind over matter. “The crossword constructor makes chaos out of language and then restores its order in the form of a neat solution,” she writes, and the anorexic sets out to impose a similar sort of tidiness onto the unwieldy body.

Yet the flesh is a repository of appetites that we cannot ultimately repress, and language, too, is a trickster intent on defying its speakers. Crosswords work precisely because words cannot be stripped of what Shechtman so beautifully calls their “polymorphic perversity,” because they are drenched in meanings — and because they are not just ethereal abstractions but also shapes and sounds.

The very genre of the crossword relies on the recognition that language is not merely an intellectual instrument but also a substance with material properties. Shechtman, a witty and crisp stylist, evidently relishes its sensuality. She is almost lovingly attuned to all its awkward oddities, writing hilariously, for instance, of “that unholiest of hyphenates, work-life balance.”

But she also understands that words and the games that recruit them are never neutral or innocuous. By the time Shechtman embarked on her constructing career, crosswords were no longer coded as a feminine pastime. Instead, they were regarded as math-adjacent and therefore masculine. “During Shortz’s thirty-year tenure at the Times,” Shechtman writes, “roughly 80 percent of the paper’s puzzles had been created by men.” No Black female constructors were featured in the paper until 2021, a scandal Shechtman rightly deems “shocking.”

The authorship of crossword puzzles is not unrelated to their content. Ever since Hale set out the rules for constructors, according to which “the only requirement [for a crossword clue] is common sense,” cruciverbalists have been custodians of language, as Shechtman discovered when she tussled with Shortz over which words were, in the lingo of the business, “puzzle-worthy.” She bristled when Shortz removed “male gaze,” an allusion to an influential feminist theory, from one of her puzzles, and she soon realized that their clashes were implicitly disagreements over the role of constructors. Was it their job to reflect the linguistic biases of the paper’s readership, or to correct those biases? To reflect that slippery and devious fiction, “common knowledge,” or to reimagine it? Many constructors, it turns out, are not so constructive after all.

But Shechtman is a constructor in the best sense of the word. “I am strongly of the opinion that looking up an unknown word or phrase is not cheating but learning,” she writes. Her puzzles are designed to teach us. Her book, at once a celebration and demonstration of the riotousness of words, does the same.

Becca Rothfeld is the nonfiction book critic for The Washington Post.

The Riddles of the Sphinx

Inheriting the Feminist History of the Crossword Puzzle

HarperOne. 271 pp. $29.99



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