I met Richard E. Maltby Jr. while working as a Harper’s intern in the spring of 2022. An Englishman in New York, my colleagues were bemused by my lunchtime lucky dip: selecting a cryptic crossword at random from the archives and attempting to solve it before the hour was up. Maltby’s cryptics became the basis of a fond daily ritual, and after I contacted him, of our friendship. Once I joined his team of testers, we met at a diner to discuss each other’s latest grids, where he indulged me as an equal, charitably providing feedback on my first cryptics.

This year, Maltby, who was first hired by the Harper’s editor emeritus Lewis H. Lapham, celebrates fifty years writing the magazine’s monthly cryptic crossword. (To mark the occasion, I’ve included a cryptic clue below.) Maltby describes the puzzle as a “little universe on the back page,” like a god estranged from his own intelligent design. It is “kind of lonely,” he told me. But for his many loyal solvers, Maltby has always made this universe feel lively and large.

Man shortly with fifty years penning teasers primarily – bravo! (6)

Roddy Howland Jackson: Take us back to your first puzzle. How did you come to write cryptics for Harper’s?

Richard E. Maltby Jr.: Stephen Sondheim famously wrote an introduction to British cryptic puzzles in the first issue of New York magazine, in 1968. He did one each week. I became addicted. The puzzles seemed to attract lyricists. I tried my hand at creating a puzzle or two during that year, and Sondheim published them. After a few years, Sondheim, who was going into rehearsal with Company, found it too hard to write the puzzle, and announced that he was stopping. I couldn’t stand that the puzzles wouldn’t appear, so I offered to take them over. Sondheim and the editor, Clay Felker, agreed. After some years, my writing career began to take off, so I had to stop the New York puzzles, too.

A couple of years later, Lewis Lapham asked if I might resume them, the attraction being that Harper’s was a monthly and I would only have to design a new puzzle every four weeks. I decided that I could do the Harper’s puzzles if I worked with Ed Galli, an exceptionally smart puzzle tester from my tenure at New York. Ed would do the diagram and we’d co-write the clues. This worked out for a decade or so until Ed had a stroke, and I had to step in. I’ve been doing them alone ever since. I have yet to get tired of clue-writing. The English language never fails to offer new tricks and mysteries.

RHJ: You once said that cryptic puzzles “make a game out of the mysteries and anomalies of our language.” How have those mysteries and anomalies changed in the last fifty years? Has the game evolved?

RM: I don’t think the mysteries have changed at all. English is simply a bottomless well of opportunities. It is a living language that expands each year, and there is no end to its surprises. But my real feeling is that these puzzles were invented because of the nature of the English language itself.

The truth is—and this may come as a surprise to some of you—the English language does not exist. English is an entirely borrowed language. There was Anglo-Saxon, and overlays of Norse from the Vikings, then the French invasion brought some upper-class words: “beef” for “cow,” “mansion” for “house.” There was also the influence of Christianity, with its layers of Latin roots and the attendant erudition of Greek, all of which pepper the scientific terms in chemistry, botany, astronomy, and so on. And then there are all the words from the British empire: “jungle,” “shampoo,” “pajamas.” Layer upon layer. Out of this massive word collision come all the curiosities that make English so baffling and exciting. “Lead.” Why does that mean “to show the way” and also “a heavy metal”? There is no etymological connection between these two words, but there it is: the same word with different meanings.

The truly astonishing thing is that we maneuver through these anomalies in almost every sentence we write and speak. If you are playing Clue and you announce your suspicions lead you to a lead pipe, we are not confused. Why aren’t we? Because the English language is so complex, our daily conversation operates entirely on assumptions. We assume that we mean something and that our particular meaning is being received, but the words could mean many other things. Even that sentence: why does mean mean “mean” instead of “nasty”? We all just know what we mean. When you think of it, it is actually remarkable that we communicate at all.

The point of a cryptic clue is to use these assumptions against you, to mislead you, to trick you into thinking of the verb when the answer is a synonym for the noun. Here’s a clue from one puzzle: “By coating finish, you get working supply? (5).” It reads like a sentence from an instruction manual. But in the world of cryptic clues, a solver would know to mentally repunctuate the first half of the clue to tell you how to spell the five-letter answer. If BY “coats” END (a synonym for “finish”), you get BENDY. It might take a moment to realize that “supply” in the clue isn’t a noun, but rather an adverb. That is the game I play with the solvers: to turn their assumptions against them, and trick them into misreading something that is right in front of their eyes. To my mind, that is fun. My goal is not just to write a clever clue. I want you to laugh out loud when you realize you have been hoodwinked by the English language.

RHJ: As a puzzle maker, you’re highly aware of the solver. It demands a very literal form of readerly engagement. Is your relationship with your solvers more adversarial or collaborative?

RM: My goal with the clues is to make you laugh. A smile is okay, a bit of a chuckle is acceptable, but I really want the all-out laugh. Try this one: “Sign for and take $100 off recreational vehicle on beach (9).” Take C (one hundred in Roman numerals) off CAMPER (“recreational vehicle”) on SAND (“beach”). Do you see the definition? “Sign for and.” AMPERSAND. Could it be more obvious?

RHJ: While you’re speaking outside of the constraints of the cryptic clue, is there anything you want to tell your solvers?

RM: Frankly, I would not mind getting more mail. Tell me most of all if something made you laugh. But also tell me if a clue annoyed you. It might be my fault, in which case I’ll improve as a clue writer. It’s always been kind of lonely on the back page. I could use some visitors.

RHJ: The technological landscape for puzzles has changed dramatically in the last fifty years. While tools like word engines may have made it easier to create puzzles, tools like anagram solvers have certainly taken some of the valor out of solving them. How has technology affected your puzzles?

RM: I am too stupid or tech-illiterate to make use of technology. I use A2z Word Finder to create the grids and search for interesting, fun anagrams. That’s it. I can’t even touch-type. And don’t ask me about AI.

RHJ: In Joshua Rosenblum’s book, Closer Than Ever, which recounts your songwriting partnership with David Shire, Rosenblum speaks of the “characteristically Maltby-esque concision and economy” in your lyrics. “Maltby-esque” is also a word used to describe your puzzles. What makes a puzzle Maltby-esque?

RM: It’s funny, but ahead of this interview, I checked out a forum for solvers of my puzzles. The first comment I saw was that my clues were often “wordy.” So much for concision.

My songwriting is economical because I prefer to write to the music. Having the music first always leads to language I would never pick on my own. In music, the structure of a sentence is given in advance: where the accents are, what the rhythm is. If I have a thought I want to express in that sentence, I have to use the vast arsenal of the English language to find a way to express that thought while fulfilling the music’s rhythmic and tonal demands. It is often very hard. Something perfect in spoken language has to give way to the musical constraints. But when it succeeds, it is a creative thrill.

My favorite example is in a song from the musical Baby. A young pregnant woman feels her baby kick, and she suddenly has a perception of being part of a continuum of life that extends through all time. She sings: “And all these things I feel, and more / My mother’s mother felt, and hers before.” I was able to get three generations into ‘my mother’s mother felt’ and then, in only four more syllables, got all the other generations: “And hers before.” I can’t tell you how long it took to find that solution (including a rhyme!) and how satisfying it was that the result was so simple, graceful, elegant—and completely unforced.

RHJ: During Donald Trump’s first impeachment trial in 2020, the Republican senator Rand Paul was spotted doing a crossword puzzle instead of listening. Paul’s spokesperson commented, “All smart people do crossword puzzles.” Where do you think crosswords fall on today’s cultural spectrum? If the puzzle has politics, what are they?

RM: Cryptics have a different dynamic from straight crosswords—it’s almost like the puzzle maker is saying “I’m smarter than you.” Did I fool you? The answer was right there, and completely fair, and I tricked you into not seeing it. See how smart I am.

I’m going to reveal my political bias here, but I can’t imagine anyone in an administration intent on lying and disregarding fairness would ever be drawn to cryptics, at least not mine. Not to mention that these puzzles are committed to the idea that words have actual meanings.

RHJ: What lies in store for the cryptic crossword in the next fifty years? Is it in good health?

RM: As far as I can tell, the audience is growing. The cryptic’s devotees were a small merry band when Sondheim introduced it to America. Now the New York Times produces them semi-regularly. Some of the puzzle creators are very clever. They don’t, however, strive to make people laugh. I wonder what AI will produce. I suspect creating a clue involves a subtlety of language that may escape robots.

RHJ: You once told me that you enjoy solving your own forgotten puzzles from decades past. Do you have a favorite puzzle, theme, or clue from that time?

RM: “The definitive manifestation of the human comedy is a crime (12).”

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