Stephen Sondheim didn’t just change musicals. He changed crosswords.

Stephen Sondheim, by his own admission, had a “puzzle mind.” The incomparable Broadway lyricist and composer, who died on Nov. 26 at the age of 91, had a lifelong addiction to games and puzzles, and was particularly obsessed with diversions that involved the most devious kinds of wordplay.

As Isaac Butler observed in Slate’s obituary, Sondheim’s musicals can feel like puzzle palaces, and to enter one is “to look at the unsolvable puzzle of life, and find endless riches within it.” But throughout Sondheim’s life, there was an inevitable tension between the tidiness of puzzles with clearcut solutions and the intractable puzzles of daily existence. Sondheim once chalked up the existence of his “puzzle mind” to a reaction against his “chaotic early life.” After all, he explained in 1980, “the whole idea of art is bringing order out of chaos. It’s the organization of material and that really is what making a puzzle is.”.

Sondheim is particularly remembered among connoisseurs of word puzzles for his role in introducing Americans to British-style cryptic crosswords, in which clues must be unpacked by teasing apart intricate wordplay embedded within. The crosswords that he created for New York Magazine in 1968 and 1969 were instrumental in popularizing the cryptic genre on this side of the Atlantic. At the time, he scoffed at American crosswords that merely served as “a mechanical test of tirelessly esoteric knowledge,” as he sought a more satisfying “test of wits.”

Sondheim attributed his love of both puzzles and musicals to the mentorship of the legendary Broadway lyricist Oscar Hammerstein II, who nurtured Sondheim’s agile mind from an early age. When Sondheim moved with his divorced mother to a Pennsylvania farm and attended a nearby Quaker boarding school, he befriended Hammerstein’s son Jamie. Hammerstein welcomed young Stephen as an honorary member of the family—a family that was immersed in games and puzzles.

Hammerstein particularly enjoyed a style of crossword called “Puns & Anagrams,” which could be found every few weeks in the New York Times below its main puzzle. Crossword editor Margaret Farrar had launched Puns & Anagrams in the pages of the Times early on, shortly after the introduction of crossword puzzles to the newspaper in 1942 as a diversion for readers overwhelmed by the bleak news of World War II.

In a Puns & Anagrams puzzle, wordplay stays on the lighter side. In one 1942 puzzle from the Times, “Here there is rain, too” is the clue for ONTARIO, since it’s an anagram of “rain, too.” As Sondheim remembered in a 1983 interview in Games Magazine, he was about 14 years old when Hammerstein introduced him to Puns & Anagrams, and he set about creating his own and submitting it to the Times. “They sent it back saying, ‘We’re very impressed, it’s very perspicacious,’ which was a word I had to look up,” he recalled.

Sondheim had to look across the Atlantic to satiate his more sophisticated puzzling urges. After graduating from Williams College in 1950 and moving to New York, he became fast friends with Burt Shevelove, with whom he would later collaborate on A Funny Thing Happened on the Way to the Forum. An Anglophile, Shevelove was partial to the cryptics in the London Times, and he and Sondheim bonded over solving them. The two of them moved on to solve puzzles in The Observer set by Ximenes (the pen name of Derrick Somerset Macnutt) as well as the even more diabolical creations in The Listener, a weekly magazine published by the BBC.

The Listener crosswords were “the puzzle maker’s puzzle, really esoteric and quite extraordinary,” Sondheim recalled in an interview published earlier this year. “Of all the publications, The Listener had the most elegant, complicated, devious, interesting puzzles.”

A 1956 Listener puzzle solved by Stephen Sondheim.
Courtesy of Will Shortz

New York Times puzzle editor Will Shortz got to know Sondheim in the 1980s when he was an editor at Games Magazine, and Sondheim ended up giving him a remarkable personal archive: all of his solved copies of puzzles from the Listener going back to 1950. “Sondheim’s earliest Listener puzzles are simply cut out from the magazine and left unsolved,” Shortz told me. But as the years went on, Sondheim became increasingly confident filling out the grids, which in the Listener required following complex sets of instructions on top of the wordplay in the clues.

One of the earliest fully completed Listener grids that Shortz found in Sondheim’s archive is dated Feb. 16, 1956. By that time, Sondheim had landed the job writing lyrics for West Side Story, in his career-making collaboration with the composer Leonard Bernstein. Bernstein, as it turned out, was also a great lover of word puzzles, and Sondheim introduced him to the Listener crosswords as the pinnacle of the art. “The Listener was published Wednesday and would reach the U.S. on Thursday,” Sondheim recalled in 2004. “I’d grab a copy on my way to work on West Side Story, and I got Leonard Bernstein hooked. Thursday afternoons no work got done on West Side Story. We were doing the puzzle.”

When Sondheim turned 27 on Mar. 22, 1957, Bernstein gave him a special gift. It was a custom-written poem, which began:

Stephen Sondheim is a maker and solver of puzzles:

The jigsaw of his mind, the crossword of creation, and

Especially the cryptologies of the heart.

Naturally, the whole thing was an acrostic, with the first letter of each line spelling out STEPHEN SONDHEIM.

A decade later, Sondheim was an established Broadway name, and he began filling his apartment on the Upper East Side of Manhattan with a collection of antique games and puzzles. (Sondheim’s collection inspired the house full of games in the play and movie Sleuth, written by his friend Anthony Shaffer.) He was still hooked on those Listener puzzles, and was given an opportunity to spread the cruciverbalist gospel when Clay Felker, the co-founder of New York Magazine, asked him to contribute a crossword to the magazine’s first issue in April 1968. That became a regular gig for the next year and a half, though the frequency of his crosswords gradually declined. He gave up constructing the puzzles entirely when he got too busy working on a new musical, Company.

Unlike the tame Puns & Anagrams puzzles he solved as a teenager, Sondheim didn’t pull any punches in those New York Magazine crosswords, explicitly modeling them on the ones in his beloved Listener. In the book The Crossword Century, Alan Connor put it this way: “To introduce newcomers to the delights of the British cryptic with Listener-style puzzles is a little like persuading people to take a pleasurable healthy stroll on the weekends by dropping them blindfolded into the Borneo jungle equipped with a butter knife for hacking through the undergrowth. But you can’t blame Sondheim for trying.”

To be fair, Sondheim’s puzzles were more accessible to solvers than the Listener concoctions of the day. Foggy Brume, a top puzzle constructor, solved some of Sondheim’s crosswords on his Twitch stream this past week. When I asked him about Connor’s characterization, he said it was a bit of an exaggeration. “It’s more like if you were dropped in the middle of the Borneo jungle and you were given a pretty good machete, but maybe a wonky compass,” Brume said.

Sondheim’s mischievous voice came through in his cryptic clues. One of his New York crosswords includes the punny clue “Zecret zyztem you might catch with zniffles?” The answer is CODE, which sounds like how you would say “cold” if you had a cold. A more complex Sondheimian clue is “Broken harmonicas found floating in Manhattan.” The word “broken” indicates you need to anagram the letters of “harmonicas.” The answer, MARASCHINO, is something you might find floating in a Manhattan — the cocktail, that is.

Despite their level of difficulty, Sondheim’s crosswords—and those of his successor at New York Magazine, fellow lyricist Richard Maltby—ended up inspiring a new generation of American puzzle solvers and constructors. I checked in with Henry Cox and Emily Rathvon, the husband-and-wife duo widely recognized as the country’s foremost creators of cryptic crosswords. They first came across Sondheim’s puzzles because Cox’s father had a stash of photocopies, and one summer day in 1976 they plunged into solving them. Cox and Rathvon lovingly recall “Sondheim’s world of wonders”: “Words that played charades! Words that reversed themselves in a fun-house mirror! Anagrams!” Soon they were making their own for The Atlantic, where they contributed variety puzzles for more than three decades before switching to The Wall Street Journal.

Despite Sondheim’s short tenure as a crossword constructor, his impact continued to reverberate. “Sondheim was the first cryptic crossword composer in the U.S. to follow square-dealing rules,” Shortz explained. “By ‘square-dealing,’ I mean following the modern conventions of fairness in cluing, in which each clue contains a definition or direct hint for the answer along with a secondary description of it through wordplay. As a result, Sondheim had an enormous influence on the development of cryptics here. Previous attempts had been idiosyncratic and sloppy.”

Sondheim’s creations—whether crosswords or musicals—could never be called “sloppy.” It was that meticulous, order-seeking “puzzle mind” at work. When Dean Olsher interviewed Sondheim for his 2009 book about crosswords, From Square One, Olsher prodded him on “the close kinship between fitting words into a grid and fitting lyrics into a melody.” Sondheim reluctantly responded by saying, “Yeah, I suppose so,” and repeated his favored line about “order out of chaos.” But he declined to make too strong a connection, saying that making order out of chaos is simply “what artists do.” Bernstein may have lauded his friend as the solver of the “crossword of creation” and “the cryptologies of the heart,” but Sondheim never mistook one for the other. “One of the great things about crossword puzzles is, there’s a solution,” he said. “And that’s unfortunately not true of all the puzzles in life.”

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