The New York Times ran its first-ever crossword puzzle 84 years ago. Titled “Headlines and Footnotes,” the grid — 23 rows stacked neatly with a smattering of black boxes — boasted the bylines of Charles Erlenkotter, a seasoned constructor, and Margaret Farrar, the puzzle editor. The paper had previously turned up its nose at such pursuits.
But, in the wake of the 1941 attack on Pearl Harbor, Lester Markel, The Times’s Sunday editor, decided it was time to give a little. In a memo to Arthur Hays Sulzberger, the paper’s publisher, Markel urged a bold pivot. “We ought to proceed with the puzzle,” he wrote, framing it as an invitation to readers, fretting over a world at war, to partake in a bit of playfulness. But we’d venture that even the most hard-core solvers in 2026 would struggle to fill the entire grid.
Even Will Shortz, The Times’s lead Crossword editor since 1993, has no trouble admitting that it’s a doozy. It simply has “too many things I don’t think I should have to know,” he said. Erlenkotter set the tone immediately with 1-Across [Famous one-eyed general], which references Archibald WAVELL of the British Army, who served in the military for over four decades.
Later, at 30-Across [Name of 3 successive Pharaohs] solves for a moniker that’s hardly on the tip of anyone’s tongue: USERTESEN. This answer has not appeared in a single New York Times Crossword since. Image Though Shortz does his best to imbue today’s grids with a timeless quality, every puzzle is ultimately an artifact of its era — not quite frozen in amber but certainly reflective of the culture in which it was curated.
Even Shortz’s puzzles from the 1990s include trivia that solvers now might have long forgotten. A look at the very first edition makes clear just how much the Crossword has evolved over the past eight decades. With the 1942 puzzle, Farrar established several principles that still remain intact.
Rotational black square symmetry — the puzzle can be turned 180 degrees to yield the same pattern — holds true today. In a broad sense, the structure of the cluing is also similar: All clues must follow the same parts of speech as their answers. [Passageways] are STREET S (48-Across) and [Fry quickly] is SAUTE (47-Across). The clues also avoid using “to” at the front so things substitute perfectly: (to) “fry quickly” = (to) “sauté.”Modern standards dictate lively vocabulary, a focus on general knowledge and pop culture and the requirement that all answers, especially the less familiar ones, don’t intersect with other hard-to-guess words.
In 1942, the world of wordsmithing was decidedly different. The Times’s crossword puzzle was meant to be more “newsy” than those published by competitors, intended to mesh well with its canvas. Despite having no obvious theme, the first puzzle was loosely spun together around of-the-era news content.
In it, you’ll find references to cannons, naval bases, defense stamps and not one but three matter-of-fact mentions of the Nazis, such as 103-Down: [Port on Zuider Zee, occupied by Nazis], the clue for AMSTERDAM. According to Shortz, Farrar wasn’t actually fond of the instructions she received to make the puzzle part and parcel of the newspaper’s journalism.“When no one was looking, she started to downplay the amount of news and increase the number of literary references and other things,” he said. It’s an ethos he still follows, sprinkling in clues and answers that feature movie titles, candy brands and internet slang, for example. “Nowadays, everything in life is fair game for a crossword,” he said.
While Farrar liked to avoid any references to death, disease and taxes, Shortz believes one or two references to serious matters are permissible in the puzzle. Ultimately, though, “you do want the crossword to be upbeat and to leave peo...
Source: New York Times Top Stories · Summarized by HeadlinesBriefing