The Puzzling Story of How Cryptic Crosswords Crossed the Atlantic
Stephen Sondheim gets credit for popularizing cryptic crosswords in the U.S., but there’s a lot more to the story.
There’s a burgeoning interest these days among American crossword fans in a puzzle style that’s long been seen as a chiefly British pursuit: the cryptic crossword. Spend some time in the various online hangouts of cruciverbalists, whether it’s on indie puzzle blogs, Twitch streams, or Discord servers, and you’ll find Americans enthusiastically digging in to cryptics, both solving and making them.
The U.S. contingent of cryptic-crossword fans owe a debt of gratitude to the great Broadway wordsmith Stephen Sondheim for popularizing the puzzle genre on this side of the Atlantic more than a half century ago. As I wrote for Slate after Sondheim died on Nov. 26, 2021, no one did more to introduce the wordplay-laden form to American audiences when he created puzzles in New York magazine in 1968 and 1969. But as I researched the Slate article, I discovered that Sondheim was hardly the first American to take an interest in cryptics. He was following in the footsteps of less-heralded puzzlemakers who were similarly entranced with the devious British approach to crossword construction.
The criss-crossing trans-Atlantic story starts in New York, where a Liverpool-born journalist named Arthur Wynne created what is recognized as the first crossword puzzle, in the Dec. 21, 1913 issue of the New York World. It would take another decade for the crossword craze to truly take off, when Simon & Schuster began publishing crossword books in 1924. Margaret Petherbridge (soon to be known as Margaret Farrar), who got her start working for Wynne, edited the books with her two less-remembered colleagues, Prosper Buranelli and F. Gregory Hartswick.
Among their other achievements, Farrar, Buranelli, and Hartswick invented the diagramless crossword when they went to lunch in 1925 and forgot to bring the grid to a puzzle they were editing. Hartswick, the story goes, worked out the grid on the back of a menu, just from the clues, and the diagramless was born.
Crossword-mania crossed the Atlantic early on, and the earliest British crosswords followed the straight-definition style of cluing. But that started to change in 1926 when Edward Powys Mathers, who used the torturous pen name Torquemada, began “setting” crosswords (as they say in the U.K.) for the Observer. Mathers gradually invented what we now recognize as standard cryptic cluing, and other British newspapers followed suit. Originally such puzzles were simply called “Torquemada style.”
When did American puzzlers start taking notice of Torquemada and his fellow setters? To answer this question, I checked in with New York Times puzzle editor Will Shortz, whose knowledge of crossword history is second to none. Shortz is also the historian of the National Puzzlers’ League, and it turns out that it was in the pages of The Enigma, the NPL’s monthly magazine, where cryptic crosswords first gained attention. In the Oct. 1930 issue of The Enigma, Geoffrey Gilbert, whose NPL pen name was Tweedledee, reported on “the crossword puzzle as now published in such English papers as the Observer and the Times.” These puzzles, Gilbert explained, used “a comparatively large number of unkeyed letters” (what we’d now call “unchecked” letters), cutting down on the usual crossword-ese of American puzzles. And he marveled at how “the definitions are ingenious and tricky.” “They demand mental agility,” he wrote, “and when they are cracked they leave the solver with the pleasant feeling that both he and the constructor are rather clever fellows.”
Five years later, the new British crossword style would get much wider exposure thanks to none other than F. Gregory Hartswick, Margaret Farrar’s co-editor and accidental inventor of the diagramless. Hartswick was fascinated by the Torquemada puzzles in the Observer, and he spread the word in the Aug. 1935 issue of Esquire, in an article entitled, “Mr. Torquemada of England.”
Not only did Hartswick reproduce a Torquemada puzzle for the article, he also created his own, using the byline “Mr. Tantalus of America.” He followed the Torquemada format of using a barred grid, and the clues emulated the British style, which had not yet fully evolved into the standard cryptic approach, often relying on puns and allusions. Wordplay indicators were still a work in progress, making clues a bit rudimentary to the modern eye. (A sample anagram clue: “O, prof! Demonstration, please!” for PROOF.)
A year later, in 1936, Hartswick continued spreading the gospel of Torquemada in the 40th Series of Simon & Schuster’s The Cross Word Puzzle Book. The final puzzle in the book was yet another Torquemada-style cryptic, with Hartswick now using the pen name Gregorian. As the editors said in the book’s foreword, “Our own feeling is that there is definitely a place for this type of puzzle here in the American Scene.”
Some other American experiments with the cryptic form appeared soon after — Will Shortz shared some examples in the magazine Games Digest, published in 1937, which were something of a hybrid between the U.S. and U.K. styles. But the American scene would not truly begin finding a place for the cryptic puzzle type until the 1940s.
Margaret Farrar, when she became the first New York Times crossword editor in 1942, developed a kind of variety puzzle inspired by Torquemada by way of Hartswick, but made more palatable to American solvers. When Farrar published the first Times crossword in the Sunday Magazine of Feb. 15, 1942, directly below it and filling up the rest of the page was a smaller grid titled “Riddle Me This,” with the explanation, “Here are puns and persiflage, anagrams and homonyms, all fair game for the amateur sleuth.”
(If you’d like to solve the puzzle, it’s accessible here in Across Lite .puz format — made available in 2010 when Patrick Merrell wrote about it for the Times Wordplay blog.)
The byline of the puzzle was “Anna Gram,” and as Stan Kurzban and Mel Rosen observed in their 1980 book The Compleat Cruciverbalist, “‘Anna Gram’ has been used as a pseudonym, or nom de puzzle, to conceal the identities of several puzzle constructors, including Margaret Farrar herself.” So we can safely assume that Farrar was the one to construct the first of what would soon be known as “Puns & Anagrams” puzzles. Farrar would keep P&As in the regular rotation on Sundays, along with diagramlesses and other variety puzzles.
While Puns & Anagrams are often looked down on by crossword purists as a diluted form of cryptics, those early P&As in the Sunday Times played an important role in the American cryptic-crossword story, since they piqued the interest of a young Stephen Sondheim. As I discuss in my Slate piece, when Sondheim was a teenager, his mentor and surrogate father figure Oscar Hammerstein introduced him to the Puns & Anagrams puzzles in the Times. He even submitted his own to the paper, but it was politely rejected. Those P&A puzzles, it turned out, would be a kind of gateway drug for Sondheim.
With Farrar publishing not-quite-cryptic Puns & Anagrams puzzles in The Times, it would take a different publication to begin bringing British-style cryptics to an American audience on a regular basis. That happened in 1943, when the weekly magazine The Nation started publishing cryptics constructed by Jack Barrett, a longtime contributor to the Simon & Schuster crossword books. As Will Shortz detailed in the May 1979 issue of Word Ways, Barrett had crossword experience on both sides of the Atlantic: while living in England, he created a crossword competition for the News of the World and helped launch a daily puzzle in the London Times in 1930.
Barrett adopted the classic British lattice-like “block cryptic” with alternating checked and unchecked squares. In the very first Nation cryptic, appearing in the Feb. 20, 1943 issue, Barrett helped solvers out by providing all of the unchecked letters in the grid.
Starting with the third puzzle, on Mar. 6, 1943, the training wheels came off, and solvers were given completely empty grids. Early on, Barrett called them “cryptogrammatic crossword puzzles,” even though British newspapers had already begun referring to “cryptic crosswords” as early as 1930. But when Barrett collected the first batch of puzzles in The Nation’s Crossword Puzzle Book in 1944, he called them “cryptic crosswords” in the foreword.
Shortz notes that there were other cryptic forays on the American scene in the 1940s, including those from bridge experts Albert Morehead and Geoffrey Mott-Smith, who published in the magazine Blue Book. Morehead collected crosswords he edited in the 1943 volume Doubletalk Crossword Puzzles, and four cryptics by Jack Luzzatto were also published in Morehead and Mott-Smith’s Signet Crossword Puzzle Book of 1948. (Luzzatto would go on to be one of the most prolific constructors of regular crosswords for the New York Times, pioneering wide-open grids.) Unlike Barrett’s puzzles, the ones from Morehead and Mott-Smith were fully checked grids but with cryptic-style clues.
Barrett’s tenure at The Nation came to a sudden end four years after it started, when he died in a boating accident. His death was reported in the July 26, 1947 issue of the magazine, along with an announcement that they would be trying out candidates for his successor. Puzzles were published credited only to “Mr. X” and “Mr. Y,” and readers voted for their favorite. On Oct. 18, they revealed that the winner was “Mr. Y,” his real name being Frank W. Lewis. Lewis would go on to produce Nation cryptics for more than six decades. His final puzzle appeared in Dec. 2009, and he died at the age of 98 the following year. (Joshua Kosman and Henri Picciotto carried the torch at The Nation until the magazine stopped publishing cryptics in 2020.)
For many years, The Nation was something of a lonely outpost for the American cryptic. So, when Stephen Sondheim introduced his first cryptic in the Apr. 8, 1968 issue of New York magazine, he could accurately say that this “test of wits” was “inexplicably nonexistent in the United States apart from The Nation and an occasional Sunday edition of The New York Times.” Besides, Sondheim wanted to go far beyond what Barrett and Lewis had been publishing in The Nation, instead modeling his New York puzzles on the far more diabolical British variety cryptics that he had been solving in The Listener since the 1950s. Unlike the gentle approach of Barrett with his filled-in unchecked squares, Sondheim went in the other direction, amping up the difficulty for his unsuspecting readers.
And yet those New York puzzles by Sondheim — as well as those by his successor, fellow lyricist Richard Maltby Jr. — sparked the interest of a new generation of American crossword buffs. Sondheim and Maltby (the latter of whom went on to construct puzzles for Harper’s) set the stage for Emily Cox and Henry Rathvon, who began writing cryptics for The Atlantic in 1977 and remain the gold standard for American constructors. Cox and Rathvon were joined by a cohort of outstanding puzzlemakers who came of age at Games Magazine in the 1980s, like Will Shortz, Mike Shenk, Henry Hook, Merl Reagle, and Fraser Simpson. That lineage continues with a new crop of brilliant American cryptic constructors publishing in venues like The New Yorker and The Browser. While we celebrate Sondheim for blazing the trail, let’s also give it up for Hartswick, Barrett, and the other unsung pioneers in this puzzling tradition.
