• Tue. Mar 28th, 2023

Will Shortz’s Life in Crosswords

ByGurinderbir Singh

Feb 15, 2023

When Will Shortz took over as the crossword editor at the Times, in 1993, he set out to make the puzzle younger. He published more contributors in their twenties and thirties, and favored clues with a modern sensibility: Greek prefixes and musty arcana were largely swept away, replaced by sitcoms, snack-food brands, and sprightly wordplay. Now, at the age of seventy, and approaching his thirtieth anniversary at the paper, he is a member of the established cohort he once defined himself against. Part of his job, as he sees it, is to adjudicate what any puzzler should know. But he is a self-described “older white guy,” and his judgments have drawn criticism, at times, for catering narrowly to his demographic. To a rising generation of crossword enthusiasts, he is at once a revered maestro and a frustrating embodiment of the Old Guard.

Although he resists crossword-clue relativism, and maintains that some references are simply more significant than others, Shortz has changed with the times in certain ways. He now shares his duties with a team of associate editors, and he happily acknowledges that their array of backgrounds and habitus has made for a better crossword. Navigating these changes seems to have done nothing to dampen Shortz’s enthusiasm for the job; the man was clearly put on this earth to puzzle. In our conversation, which has been edited and condensed, we talked about some non-puzzle things, too: his love of table tennis, his cameo on “The Simpsons,” and the surprise of finding his first serious romance, late in life. Afterward, he sent me a few of his favorite crossword clues, which you can attempt to solve below.

We’re talking over Zoom, and you’re in your home, in Westchester. I’ve heard that you have a whole collection of puzzle-related ephemera up there. Are there any collector’s items you can tell me about?

I have what I believe is the world’s only copy of the first crossword puzzle in private hands. It’s the Fun section of the New York World from December 21, 1913.

What is it like?

It’s in the shape of a hollow diamond. The first word across was “fun,” that was filled in for you. It had the word “dove” twice, one of them clued as the bird and one as the past tense of “dive,” so that’s how they dodged that accident. Still a flaw, I think.

The Fun section of the one of New York World’s 1913 issues.Photographs by Jeremy Liebman for The New Yorker

A diamond-shaped crossword from a 1913 issue of the New York World.

Crossword puzzles have come a long way since 1913.

To put it mildly.

When did you first get into puzzles? Do you have an earliest memory of solving a puzzle?

I started making puzzles when I was eight or nine. I sold my first one, when I was fourteen, to my national Sunday-school magazine.

In the eighth grade, when asked to write a paper on what I wanted to do with my life, I wrote on becoming a professional puzzle-maker. That was always my dream. I remember a questionnaire I took in grade school where you would fill out all the things you like and don’t like, and then find what profession you’re best suited for. I remember adding up my figures, turning the page, and looking to see puzzle-maker on that list of professions. And not surprisingly, puzzle-maker was not there.

You went to Indiana University, where you designed your own major in enigmatology. I assume a lot of your studies were about the history of puzzles and making puzzles?

My junior year, I found a professor in the English department who liked crosswords and was willing to work with me, so every couple of weeks I took a crossword that I had made into his office as he sat and solved it and critiqued it. That’s how I made my first professional-quality crosswords.

Every course I took on puzzles was created by me. I took courses on mathematical puzzles, logic puzzles, the psychology of puzzles—which is, first of all, what’s going through our brains as we’re solving problems, and second, why do we as humans find puzzle-solving so compelling?

When I graduated from Indiana, I went to law school, because I didn’t think it was possible to have a career in puzzles. I was selling puzzles for ten and fifteen dollars each. You’re going to starve or worse. My summer between Indiana University and law school, I had an internship with Penny Press puzzle magazines in Connecticut. I realized this is how I could have a career in puzzles: by editing them.

You went on to work at Games magazine and eventually became the editor. My sense is that, for a lot of Gen X-ers, Games was the gateway to puzzles. I was a little too young to be the target demographic, but my older brother had all the anthology books, and they seemed very different from the dusty puzzle books in the library. What was the editorial ethos like?

Up until Games, the most prestigious crosswords appeared in the Times, but, in my opinion, and the opinion of a lot of people, the Times’ crossword was stuffy. The Times’ audience was older—probably the average age of solvers was fifties and sixties. The average age of Games readers was in the thirties, so it had a different vibe. A whole new generation of puzzle-makers came up through Games magazine.

It surprised me to learn that Games was at one point published by Playboy Enterprises.

My understanding is—this is oral history, now—that Hugh Hefner himself was a fan of Games, and, around 1982, Playboy Enterprises purchased Games and held it for a number of years. I think Playboy published three magazines then: Playboy, We, and Games. It was quite the combination. I remember we had a party once at the Playboy Club in Manhattan, which was ridiculous. We also got three copies of Playboy every month during their ownership.

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