Outside the box: An interview with Will Shortz

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Will Shorts, puzzle master
Will Shortz has served as the crossword puzzle editor of The New York Times since 1993. — illustration by Brendan Wells

An evening with Will Shortz

Englert Theatre – Sept. 11 at 7 p.m. ($18-22)

If the clue were, “America’s most acclaimed contemporary crossword puzzle master,” the answer would be, unquestionably, “Will Shortz.” In addition to holding the world’s only college degree in enigmatology, the art and science of puzzle-making, Shortz has been the puzzle master for NPR’s Weekend Edition Sunday since the program’s start in 1987 and crossword puzzle editor of The New York Times since 1993; additionally, he was the editor of the legendary Games magazine for 15 years, and he is the founder of both the American Crossword Puzzle Tournament and the World Puzzle Championship. If these kinds of puzzle credentials aren’t impressive enough for you, his riddles have been featured in the film Batman Forever, he has guest-starred on The Simpsons and How I Met Your Mother and starred in the documentary Wordplay.

Shortz will be lecturing at the Englert Theater on Sept. 11, in what will, no doubt, be an engaging and animated interactive program; his animation was infectious when I had the privilege of talking to Will a few weeks ago.

Little Village: Do you have any advice for students who aren’t in a situation to individualize their major?

Will Shortz: Do what you do as a hobby, and get to be expert at it. That would be my advice to anybody who has an unusual interest and would like to pursue it as a career. I was very lucky to go to Indiana University, which has this program where you can make up your own major, and there’s someone I know who majored in magic a couple of years ago; there were people who majored in comic books through this program and who now have gone on to writing or illustrating comic books. I think there are other colleges now that may actually have majors in comic books, but that was a pioneering thing at Indiana. Most people who get into puzzles—I’m the only person who has ever majored in puzzles, but there are other people with puzzle jobs—and the way you do that is start making crosswords, get to be expert at it, get to be known for quality and, if you do all that and pursue your interests, you can get a career in it.

LV: So there wasn’t some magical way you got your foot in the door? 

WS: Well, I’ll tell you my career path. When I graduated from Indiana, in 1974, before I entered law school that fall, I wrote all the crossword magazines—and there were about a dozen at that time—asking for a summer job, and there was one that gave me a position: Penny Press in Stamford, Conn. The publisher had just taken over the magazine, there was only one holdover from the old staff, and it was a husband and wife—the wife was the editor and the husband was the publisher. The husband insisted that they hire me for the summer, and the wife didn’t want to do it, and he said if it doesn’t work out, you can send him home after two weeks. And I’m this little college kid from Indiana.

But we hit it off, I was valuable to the magazine, and I had a fantastic summer and went back to work there for the next two summers, and then when I graduated from law school, I worked there full-time for seven months. During that time, Games magazine started, and I went to work there in 1978, and they hired me because I was young—Games had a modern sensibility, they had an office that was younger than most puzzle publications, so I fit in well; I had a college degree and had been selling puzzles since I was 14, so I had the credentials; and I was there for 15 years. In 1993, my predecessor at the Times died, and I applied for the job—there were three people who were considered seriously for the position, and I was hired. Each step was built upon what went before.

LV: Right. And you weren’t afraid to put yourself out there, to ask for what you wanted? 

WS: I’ll tell you a story about that. It was in early 1978; I had actually left Penny Press, and I went for a few months without a job, and in the Sunday New York Times, I saw a classified ad for a puzzle editor—“Puzzle Editor Wanted”—and it was one of those anonymous ads, you were supposed to send your resume to a box number. Well from the wording of the ad, I was certain the ad was from Games, which is where I really wanted to work, so I figured I would beat the competition by going in directly. … So, I put on a coat and I put on a tie, took the train into New York City, walked into the office and announced I was there for their position, and it was not their ad; they did not have a position open, and the editor saw me anyway. We hit it off, we talked for 30 minutes, I started getting freelance work almost immediately and I got a job by the end of the year.

LV: Who do you consider the audience for the Puzzler on NPR? It seems a little less highbrow than the Times, no? 

WS: I call it a highbrow audience because it’s National Public Radio. What’s different about it is that if you’re a newspaper reader, and you’re not interested in the crossword, you simply turn the page. If you’re listening to NPR and I come on, you’re stuck with me for seven minutes. So I try to make the puzzle of general interest, try to make it a lively experience, so even if you’re not into puzzles, I hope it would be an interesting segment to listen to. And also, the other thing I’ll say about the radio is, on Sunday mornings, when I’m on, I’m imagining people are lolling in bed, or driving to church, or making breakfast, and they’re either not fully awake, or are, and their minds are on other things. So for my challenge puzzles, … I try to make challenge puzzles that the solver can hold in his mind without having to write anything down.

LV: What is your favorite crossword word? 

WS: Let me think … well, my favorite word is “ucalegon.” It’s a neighbor whose house is on fire. It’s in the old unabridged dictionary. It’s a bizarre word, you can’t imagine ever using it, it comes from an old Greek story, an old Greek myth. As far as words go, what excites me in a crossword is to see vocabulary that has never appeared in a puzzle before. Um, let’s take out today’s crossword … for example, today’s puzzle has KICKBOXER. Never appeared in a crossword before, anywhere. And the clue is nice—it wasn’t mine, it was from the contributor—“Fighter getting a leg up.”

LV: How do you know it’s never appeared before?

WS: There is this guy with a blog who has an electronic database of every NYT crossword going back to the mid-1980s, so if a new answer appears in a crossword, he highlights it in a different color. It’s Here’s another one: “Handheld Star Trek devices,” and the answer is TRICORDERS. That’s never appeared in a crossword before. NAILCLIPPER, ARTMUSEUM, KATESPADE, TRIBUTEBAND, KICKBOXER, OCALCUTTA, TRICORDERS, OPENEDFIRE, PRELAW—it’s just full of great stuff. Nothing bad.

LV: Are there ever any answers that you have to put in because they’re the only thing that fits?

WS: Oh absolutely. You get cornered as a constructor, and you’ve got this fantastic puzzle, and you have to use Oona, for example—Charlie Chaplin’s daughter, married to Eugene O’Neill, so there’s two ways you clue her. Anyway. You don’t want Oona in your puzzle, but I think of it as like the mortar of building a house. The house should have really strong beams, and then the little stuff that fills things in to make the house stand together—it’s the same way with a crossword. You put in lively answers or strong vocabulary—those are your girders, the substance of the crossword—and then you have to fill in the cracks with things you may not want.

LV: It’s clear that you’re really, really engaged in the world of puzzles. But in whatever spare time you have, what occupies you? 

WS: Spare time? Hah! I spend a lot of my spare time playing table tennis. In fact, I play every single day. I will play in Iowa City either before or after my presentation next month. Besides that, I read a lot and go to a fair number of movies—my favorites being science fiction, thrillers and comedies. My favorite TV shows are the Daily Show and the Colbert Report.

LV: One more question. You get fan mail all the time, but there have been certain Sundays, like when we all had to draw dogs in each little square, or fit several letters in one square, when people across the country have said, “Goddamn that Will Shortz.” So do you get the opposite of fan mail? Do you get mail cursing your very existence?

WS: Oh absolutely. I got a lot of it when I started in 1993, because I was 36 years younger than my predecessor, and there was a change of style, and I wanted to broaden the cultural references, so there’d be material and references for younger solvers, as well as old, and the puzzles were more playful, and there was more trickery and deception in the clues. Some people like that, and some people don’t. I just got a thoughtful letter from an unhappy solver a couple of weeks ago, who really longs for the days of my predecessor, when the crosswords were more vocabulary tests. And she does not like games. She says, “A crossword should not be a game, it’s a test.” And I understand it’s partly a test, but to me, crosswords are also a game, and there’s going to be trickery in the clues, and in the theme—that’s just part of the modern crossword.

Courtenay Bouvier is a University of Iowa employee, waitress, yoga teacher and writer who will, someday, finish her dissertation.

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