What Do Crossword Puzzles Really Test?

This past December, I threw a party to celebrate a major milestone in my life: the 1,000th day of my New York Times crossword-solving streak. My friends, none of them fellow cruciverbalists, poured in wearing their black-and-white best, armed with outsize praise for my presumed intelligence: How smart I must be to complete the Times puzzle every day! Their comments affirmed that the crossword—and particularly the Times one—carries a certain mystique. For 1,000 consecutive days, I had passed this bourgeois aptitude test, proving my linguistic and cultural acumen in my guests’ eyes.

Since its invention in 1913, the modern American crossword puzzle has undergone something of a reputational shift, from frivolous distraction to status symbol. In reality, the crossword is many things: a site of play, a cultural forum, a daily pleasure. And, because it traffics in language—the stuff people use to form identity, signal belonging, and ostracize others—it’s also a political entity. The writer and crossword constructor Anna Shechtman knows that casting such a pastime as political might sound ridiculous. As she writes in her new book, The Riddles of the Sphinx: Inheriting the Feminist Legacy of the Crossword, the suggestion “risks a double embarrassment: trivializing the serious stuff of politics or, maybe worse, taking trivialities too seriously.”

But Shechtman, who previously worked as an assistant to the longtime Times crossword editor Will Shortz, argues that crosswords are inevitably politicized by the people who make them. At the Times, whose crosswords have long been considered a gold standard, Shortz and his stable of test solvers and freelance constructors strive to produce puzzles that adhere to a shared sense of “common knowledge.” Indeed, some people believe that the Times puzzle arbitrates which facts and public figures every American should know—or, alternatively, what kinds of esoteric trivia are especially impressive to have in one’s back pocket. But in a nation as heterogeneous as the U.S., the very idea of common knowledge is a false one. And because mostly white men have decided what ends up in the Times crossword, its content is often circumscribed by the biases of those doing the constructing.

[Read: The hidden bigotry of crosswords]

Shechtman has spent the better part of the past decade agitating for greater diversity among puzzle makers and for crosswords that reflect a more capacious sense of common knowledge, a project she expands upon and complicates in The Riddles of the Sphinx. Her advocacy first took root during her time working under Shortz (who recently announced that he is recovering from a stroke), with whom she often clashed over what was “puzzle-worthy.” In one of Shechtman’s own puzzles, for instance, he vetoed the answer MALE GAZE; they disagreed over whether the term fell within the bounds of common knowledge. In Shechtman’s estimation, Shortz likely “pictured an audience that looked like him” when it came to deciding what counted as “relevant” knowledge.

These conflicts underscored Shechtman’s role as a woman in a male-dominated field. Women have long made up the minority of puzzle makers. According to data compiled by the constructor David Steinberg, under the two editors before Shortz, Will Weng and Eugene T. Maleska, women made just over a third of the Times’ crosswords. In the first two decades of Shortz’s tenure, per Steinberg, that proportion fell to 19 percent.

This is not necessarily an indictment of Shortz, who became editor in 1993. (Notably, the past five years under Shortz have seen a tremendous uptick inpuzzles constructed by women, who once again represent close to one-third of bylines.) The ’90s saw the confluence of two forces that hindered many women constructors: the evaporation of their free time, which had been on the decline as more and more women entered the workforce starting in the ’70s, and the advent of now-ubiquitous crossword-constructing software. The software, which usurped the traditional method of making puzzles by hand, brought more computer programmers, who tended to be male, to puzzle-making. This influx, Shechtman suggests, gave rise to a Silicon Valley–esque “brogrammer culture” in the crosswording world that may have pushed out or repelled many women.

But in Riddles, Shechtman places herself within a rich lineage of female cruciverbalists who helped pioneer the form, organizing the book around four of them: Ruth Hale, who co-founded the Amateur Cross Word Puzzle League of America in 1924; Margaret Farrar, who was appointed the inaugural crossword editor at The New York Times in 1942; Julia Penelope, author of the 1995 feminist book Crossword Puzzles for Women; and Ruth von Phul, winner of the first-ever crossword tournament in 1924. She also notes that it was women constructors—many of them housewives and homemakers with spare time—who created the first bylined puzzle, the first puzzle with a rebus, and crossword-solving contests.

[Read: The unspoken language of crosswords]

Women were also some of the puzzle’s earliest and most eager adopters, particularly during the “crossword craze” of the 1920s, in which crosswording rapidly became the nation’s pastime du jour. Because of women’s initial interest in the activity, it earned a reputation as mindless froth that lacked “any intellectual value,” as one acerbic Pittsburgh pastor put it in 1924. But in the intervening years, the puzzle evolved into an American ritual, particularly as people sought out distractions from the stresses of World War II. (That the Times, which had initially decried crosswords as a fad, launched its own puzzle in 1942 was no coincidence.) In the postwar era, a growing male presence in the crosswording world helped the pastime acquire the prestigious sheen it retains today. When the exacting Maleska became the Times’ crossword editor in 1977, he helped burnish the puzzle’s reputation for good. As Adrienne Raphel writes in her 2020 book, Thinking Inside the Box, Maleska rejected “clues that relied on pop culture or used overly colloquial phrases” and eschewed “universal accessibility,” thus turning the paper’s crossword into “a marker of a certain elite cultural status.”

When Shortz took over, he reoriented the puzzle toward common knowledge and “made it his explicit mission to introduce more varied vocabulary—including brand names, popular culture, neologisms, and slang,” Shechtman writes. As Shortz told Vanity Fair last year, “My feeling was, if younger solvers have to know older culture, older solvers should have to know younger culture.” But Shechtman and others have voiced concerns that these democratizing efforts have not gone far enough; she remains frustrated by the puzzle’s slowness to incorporate language with origins in culture produced by people of color, queer people, and women. Promisingly, some terms that Shechtman says had been rejected by Shortz have since made their way into Times puzzles, including tidying whiz Marie KONDO, K-pop band BTS, and the green-tea powder MATCHA.

The crossword community’s disagreements over the boundaries of common knowledge are not as niche—or as new—as they may appear. In his 1987 book, Cultural Literacy: What Every American Needs to Know, the English professor E. D. Hirsch argued for the importance of a shared cultural vocabulary among Americans. In the book, Hirsch included a list of about 5,000 people, dates, and terms—somewhat like the “wordlists” that most crossword constructors draw from to populate their puzzles—that might qualify. The aim of the list is not unlike what Shechtman hopes to achieve in the crosswording world: to create and embrace a canon of shared knowledge that has space for everyone. As Eric Liu wrote in this publication in 2015, responding to Hirsch’s book, this “cultural core” must be “radically reimagined if it’s to be worthy of America’s actual and accelerating diversity.”

[Read: The New York Times’ new game is genius]

The lexicon of crosswords, particularly highly visible ones like the Times’, is a public-facing compendium of that shared vocabulary. As both a pastime and a public good, the ideal crossword puzzle is not a test of highbrow sensibilities but, to use Hirsch’s term, an opportunity to improve one’s cultural literacy. It should encourage and reward familiarity with a wide range of cultures, preoccupations, and ephemera. In this way, crosswords might also serve a pedagogical function: to not just affirm what one already knows but beget new knowledge. Shechtman calls out one notable constructor who is doing this kind of work: Elizabeth Gorski, since making her Times debut in 1995, has introduced more than 1,500 terms to the paper’s crossword vocabulary, including ANNE SEXTON, QUEEN IDA, JOYCELYN ELDERS, GEORGE CLINTON, PURPLE RAIN, NATURAL HAIR, and ANDROGYNY.

In my three brief years solving the Daily Times crossword, I’ve noticed a veritable shift toward more timely and wide-ranging clues, as well as more diversity among constructors, especially in age and gender. Of course, blind spots remain: I still cringe every time I see a clue such as “12 meses” and have to enter ANO—a Spanish word that, without the necessary tilde, means “anus.” But above all, with this change under way, I’ve noticed that the puzzles have gotten more fun—drawing on more varied topics, spotlighting icons and ideas that have long gone overlooked, pushing the boundaries of the English language in exciting new directions. Taking the crossword seriously results in a better puzzle—one that challenges and teaches, surprises and delights, day after day.