The Crossword Puzzle: A 110-Year History

On December 21, 1913, the New York World's "Fun" supplement contained an unusual feature: a diamond-shaped grid of white and black squares, with a set of clues labeled "Across" and "Down." The puzzle had no black squares to separate entries — it used a more primitive convention of numbered open squares. Its creator, a British-born journalist named Arthur Wynne, called it a "word-cross."

The first clue of the first crossword in history was: "2-3: What bargain hunters enjoy." The answer: FUN. You cannot make this up.

What followed over the next 110 years is one of the most remarkable stories in the history of leisure: a single puzzle feature in a single newspaper's Sunday supplement grew into a global institution, survived wars and cultural upheavals, outlasted the newspaper industry's decline, and is today arguably more popular than at any point in its history — powered by digital apps and a vibrant online community of constructors and solvers.

Before Wynne: The Precursors

Arthur Wynne didn't create the crossword from nothing. Several word puzzle traditions laid the groundwork for what would eventually become the standard crossword format.

Word squares — grids of words that read the same horizontally and vertically — appeared in England and America throughout the 19th century. They were popular parlor games and appeared regularly in newspapers and puzzle books. The oldest known word square dates to ancient Rome: a stone carving in Cirencester, England, bears a 5x5 word square reading "ROTAS / OPERA / TENET / AREPO / SATOR" — the so-called Sator Square, which remains a subject of scholarly debate about its meaning and origin.

Acrostics — poems or puzzles where initial letters spelled out hidden words — were another precursor, popular in Victorian literary culture. Queen Victoria herself was reportedly fond of acrostic puzzles.

The missing ingredient in all of these precursors was the crossing mechanic: the constraint that letters must work simultaneously in both horizontal and vertical answers. This is what Wynne contributed. His diamond grid, for all its geometric differences from the modern rectangular grid, established the fundamental innovation that defines crosswords to this day.

1913: The Word-Cross Is Born

The 1920s: Crossword Mania

For the first decade of its existence, the crossword was largely a New York World phenomenon. Other newspapers were slow to adopt it. That changed dramatically in 1924, when two young publishers named Richard Simon and M. Lincoln Schuster launched a company called Simon & Schuster — and published, as their first title, a book of crossword puzzles.

The book came with a pencil attached to the cover. It was an instant bestseller. Within a year, crossword puzzle books had become a publishing phenomenon, and newspapers across the country rushed to add crossword features to their own pages. The crossword craze of the 1920s was genuinely extraordinary by contemporary standards.

Newspapers reported that crossword fever was causing social disruption: libraries complained that all their dictionaries were perpetually in use by puzzle solvers; British Railways installed special crossword lighting in train carriages; department stores stocked crossword-themed merchandise. One New York psychiatrist published a warning that crossword puzzles were causing a "mental epidemic." The Roaring Twenties had found its obsession.

Not everyone was enthusiastic. The New York Times, then one of the nation's most prestigious newspapers, publicly refused to publish crosswords. In a 1924 editorial, the paper declared the crossword "a primitive form of mental exercise" and expressed concern about the public's addiction to what it called "a sinful waste in the utterly futile finding of words the letters of which will fit into a prearranged pattern." The Times would famously reverse this position — but not for nearly two more decades.

The NYT Era: Standardization and Prestige

The New York Times introduced its first crossword puzzle in 1942 — motivated, ironically, by wartime. During World War II, the Times' editorial staff concluded that crosswords provided a valuable mental diversion for a population living under enormous stress. The paper's first puzzle editor was Margaret Farrar, who would hold the position for 27 years and establish the standards that define American crosswords to this day.

Farrar's key innovations were structural. She required that every white square in a crossword grid be "checked" — meaning it must be part of both an Across and a Down answer. This dramatically improved grid solvability by giving every answer multiple letter-confirmation paths. She also required rotational symmetry in the grid's black square pattern — an aesthetic choice that had the practical effect of making grids easier to evaluate visually and construct consistently.

The NYT crossword's prestige was such that publication there became the gold standard for constructors. It remains so today, despite the proliferation of indie outlets, because of what the Times represents: over 80 years of continuous quality editorial oversight, a readership of millions, and a cultural cachet that no other crossword outlet has matched.

The Golden Age: 1950s–1970s

The postwar decades represented a golden age for American crosswords. With television still new and the internet decades away, the newspaper crossword was a central feature of American daily life. Syndicated crossword puzzles — constructed by a small group of prolific professionals and distributed to hundreds of newspapers simultaneously — reached a combined readership of tens of millions weekly.

This era produced some of the most legendary figures in crossword history. Bernice Gordon, who began constructing for the NYT in the 1950s, went on to publish puzzles in the Times for more than six decades — the longest active constructing career in the paper's history. Herb Ettenson and Thomas Middleton constructed grids of such geometric elegance that they were studied as aesthetic objects as well as word puzzles.

The 1960s saw the first experiments with thematic innovation. Where early crosswords were largely fill-based — interesting words and clues, but no unifying concept — constructors began developing puzzles with elaborate theme mechanics: puns that ran through multiple entries, visual patterns formed by the grid's black squares, and hidden messages that could only be found by reading the initial letters of all answers in sequence.

The Will Shortz Revolution

In 1993, Will Shortz became the fourth editor of the New York Times crossword, succeeding Eugene T. Maleska. The appointment was not universally welcomed. Shortz, then 40, had a different vision for what the NYT crossword could be — one that emphasized freshness, wit, cultural currency, and inclusivity over the austere traditionalism of the Maleska era.

Shortz's editorial revolution had several specific dimensions. He pushed for more current cultural references — pop music, film, television, sports — that had been largely absent under Maleska. He encouraged a lighter, more playful clue tone. He actively sought out new constructors, including younger voices and those from underrepresented groups. And he elevated Thursday as the puzzle's most experimental day, encouraging rebus squares and other non-standard mechanics that pushed the form's boundaries.

The response from traditional crossword culture was mixed. Some longtime solvers and constructors felt the changes were a vulgarization of a serious intellectual pursuit. Others celebrated the fresh energy. The market responded unambiguously: NYT crossword subscriptions grew steadily throughout the 1990s and 2000s, and the paper's puzzle section became one of its most-visited digital properties.

The Indie Renaissance: 2010s–Present

The 2010s saw the emergence of a new crossword ecosystem entirely parallel to the major publications. Independent constructors — many of them younger, many from communities historically underrepresented in mainstream puzzle publishing — launched subscription-based puzzle series, tournament series, and online publications that operated outside the traditional editorial hierarchy.

Outlets like the American Values Club Crossword (AVCX), the Inkubator (dedicated to publishing puzzles by women and nonbinary constructors), Boswords, and numerous individual constructor newsletters expanded the range of voices, themes, and fill styles available to crossword solvers. These indie puzzles often felt more culturally current than their major-publication counterparts, with clue styles that reflected contemporary internet culture, greater willingness to address political and social themes, and fill that felt genuinely fresh rather than recycled from decades of prior puzzles.

The indie renaissance was also a diversity revolution. The traditional major-publication constructor pipeline had been overwhelmingly white and male. The new indie outlets actively recruited from broader communities, and their constructors have increasingly influenced editorial standards at the NYT and other major publishers — bringing new cultural perspectives, new fill vocabulary, and new cluing sensibilities to a form that had grown somewhat calcified.

The Digital Age

The New York Times launched its digital crossword in 1996 — one of the earliest newspaper features to make the transition to the web. Early digital versions were simple, but the 2010s saw the NYT invest heavily in its crossword app, which became a genuine consumer product rather than a simple web feature. The app introduced streaks, statistics, sharing features, and a polished interface that made crossword solving accessible and habit-forming for a new generation.

By 2022, the NYT reported that its Games section — anchored by the crossword but also including Wordle, Spelling Bee, and other puzzle products — had over 1 million subscribers. The crossword had become a central component of the Times' subscription business strategy.

The digital transformation changed the crossword experience in profound ways. Solvers could now compete against friends and compare times. Statistics tracked your average solve time by day of the week. The "streak" feature — which counted consecutive days of completed puzzles — created powerful behavioral engagement. For many solvers, the daily crossword became the first thing they did every morning, a ritual as anchoring as coffee.

The digital age also democratized access. Where print crosswords required a newspaper subscription or puzzle book purchase, digital crosswords brought the form to anyone with a smartphone. International audiences, for whom American newspaper distribution was impractical, could now solve the same puzzle as New Yorkers, simultaneously.

The Crossword Today: A Cultural Constant

More than 110 years after Arthur Wynne published his diamond-shaped word-cross in a Sunday supplement, the crossword is arguably more culturally embedded than at any point in its history. The numbers are remarkable:

• The New York Times crossword is solved by an estimated 3-5 million people daily.
• Hundreds of independent crossword publications operate globally, from daily apps to monthly subscription services.
• The American Crossword Puzzle Tournament, founded by Will Shortz in 1978, draws 600-800 competitors annually — figures that have grown steadily through the 2020s.
• University crossword clubs have formed across the Ivy League and beyond, bringing competitive solving to a new generation.
• The crossword has been referenced in hundreds of films and television shows, from Seinfeld to The Queen's Gambit.

The puzzle that Wynne described as a simple "word-cross" has outlasted the newspaper that published it (the New York World folded in 1931), outlasted its creator (who died in 1945 with no idea his puzzle would become a century-long institution), and outlasted every prediction that the form had reached its cultural peak. It survived radio, television, and the early internet. It adapted to the smartphone age not by compromising its essential nature but by extending it — the crossword remains, fundamentally, a space where a single solver and a well-constructed grid engage in a private dialogue about language, knowledge, and the pleasures of finding just the right word.

That essential experience has not changed since December 21, 1913. And there is no reason to believe it will change in the next 110 years.