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Will Shortz, 1998


I’m a devoted fan of The New York Times crossword puzzle, and have been as far back as I can remember, growing up in a house where the Sunday puzzle was always something of an event. For years, I’ve timed myself each week, and my average solving time has fallen to about 30 minutes. But recently – to my complete shock and delight – I finished the whole puzzle, every square filled in with no mistakes, in exactly 19 minutes. My record time (and total lack of modesty) gave me the perfect excuse to sit down and talk to the man who messes with my mind each week, Will Shortz.

Bob Nickas: Esquire magazine named you one of the “100 Best People” – right alongside Sister Wendy, the art nun.
Will Shortz:
My favorites on the list are Jack Kevorkian and Homer Simpson.

BN: Has Jack Kevorkian been in the puzzle?
No but if he ever does, now I have a nice way to clue him: one of Esquire’s 100 Best People in the world.

BN: You definitely have your fans, but most people don’t know anything about you.
Well, I was captain of the U.S. team in the International Crossword Marathon in 1989 and 1990.

BN: Captain of what team?
The American team.

BN: It’s like an Olympics?
Of crossword puzzles. There were teams from all over the world, but particularly Europe. And the idea was, you had a four-person team and you had 24 hours to create the longest crossword you could, as a team. It starts at nine in the morning and goes to nine the following morning. After 24 hours, we ended up with a puzzle that was 150 feet.

BN: Twenty-four consecutive hours and you’re not sleeping?

BN: Wow. So when did you start editing the puzzles for The Times.
Four years ago.

BN: And the person before you had been there forever, right?
He had been there a long time – Eugene T. Maleska – since 1977. So he was quite elderly, he was in his late seventies, and had a style of puzzling that appealed to older solvers, not too many younger solvers, from what I could tell.

BN: When he was editing the puzzles, many of the clues were going back to the popular culture of the 1950s, the ‘40s, even the ‘30s. Sometimes it was only because I was a fan of, say, screwball comedies that I could get any of those answers. I don’t know how anyone else was getting them. It was really like information from another generation – but carried over into the ‘80s.
And I think that’s fine, to continue that older knowledge. But puzzles should have a balance. And the problem was, in my opinion, there was very little modern stuff in the puzzle. As one of the editors of The Times Magazine told me once, if you ever saw something more recent than 1965 in the puzzle, it gave you a shock.

BN: When I first spoke to you, you said that no one in your family was involved with puzzles. You didn’t have them around when you were growing up. So how did this all start?
It was something I picked up on my own. My mother is a writer, so we were always interested in words around our family. The first puzzle I remember making was when I was eight or nine.

BN: You were eight or nine?
Well, it wasn’t professional quality. But my mom had a bridge club over for the afternoon, and to keep me quiet, she got out a piece of paper, ruled it off into squares and showed me how you make words interlock. Put me away for the afternoon – I was happy as a clam. And at the end, when everyone had left, she showed me how to number the grid, and I wrote the clues and it was my first crossword.

BN: It’s great to meet you now, but it brings me to a question – are your fans kooks or are they nice?
It’s a cross-section. What can you say about them? They’re all types of people. I run into people all the time who do the puzzle. I’ll be in a store and the person behind the counter will be solving the Sunday puzzle, so I’ll watch for a few minutes …

BN: People don’t recognize you?
They have no idea who I am. And I’ll ask how they like the puzzles, and get a feel for whether they do or they don’t before I introduce myself.

BN: And when you tell people who you are, do they ask for help?
They’re stunned, but most people are happy to meet the person behind the name they see every week. I was in an antique shop in Vermont about six months after I got the job, and the lady behind the counter was doing the puzzle. So I asked her how she was doing and she said, “I’m not doing very well since this new guy came along. I don’t like him.” So then I introduced myself. It was very funny.
When I get on the train to head up to Westchester where I live, I’ll walk along the windows before I get on the train, watching for people doing the puzzle.

BN: In the city, you see people doing it on the subway. And I, for the life of me, don’t know how anyone can manage that. For the most part, they seem to be what I call “the strugglers,” lots of things over-written, lots of blank squares. If only they were home, quietly with their cups of coffee, they might perform better.
But if you’re into the crossword, you can tune out the rest of the world. That’s one of the great things about puzzles: you don’t think about whatever problems you’re having, you can focus completely on this puzzle, and if you finish it, it’s a terrific sense of achievement. So it’s a very nice way to deal with problems. You also have to remember, when you see people struggling, the puzzles get harder as the week progresses.

BN: I didn’t know that.
They increase in difficulty. Monday is what you might call an easy/medium puzzle. And it builds up to extremely hard on Saturday. Even harder, in fact, than the Sunday puzzle.

BN: Sometimes on a Saturday, the really long clues just stay blank for a long time. At least on Sunday there’s a theme, and once you’ve figured out the theme, that really helps with the longer lines. Once I get the theme, I go for all the long ones …
Before you do the little words?

BN: Well, first I try to build up some kind of foundation, filling in one chunk of the puzzle to expand out from there. Because sometimes the theme is really elusive. Like a few Sundays ago, I got most of the puzzle even though I never figured out what that theme was.
I bet I know which one that was: “String Quintet?” There were words like “sequoia” … “Henri Rousseau Oils” was one of the answers. The gimmick was that the five vowels – A, E, I, O, U – appeared consecutively in some order within every long answer. So the five vowels made the quintet, the string was that they were consecutive. A lot of people were stymied by that.

BN: It was so incredibly hard. I was thinking, what kind of …
Twisted mind would come up with that? Well, believe it or not, the goal of the puzzlemaker is to get you to solve the puzzle, but only after a struggle. The puzzlemaker wants to twist your brain to the very end, and then, finally, you understand it and you fill in all the squares. That’s when you get the most satisfaction.

BN: Now, you’re not actually making the puzzles, you’re editing them. So are people approaching you with puzzles?
Manuscripts come from all over the country.

BN: People just submit them?
Right. Some people are regulars, and you can recognize them by the repetition of their names. Some people just submit occasionally, and others, once they’ve had one puzzle in The Times, they have achieved their goal and I never hear from them again. But they come in from all over the country. I published over 120 different puzzlemakers last year. And they don’t do it for the money. They pay is only $75 for a daily puzzle and $300 for Sunday.

BN: I never used to go near the bottom of the puzzle page – to do the Acrostic or the Diagramless – but I’ve been doing the Spiral, where the answers read in both directions and I love it.
You know, that’s my own puzzle? I make all the Spirals.

BN: Once I did one, I was hooked. If you get stuck working in from the outside, you can start solving from the inside out. I love doing them, but they don’t appear that often.
About every nine months or so. I’ll have another one coming up soon.

BN: Now, I know you have a show, and I apologize that I’ve never heard it, because I never listen to the radio, but everyone else here loves it.
Well, it’s on a Sunday morning, so you have to be the sort of person that gets up Sunday morning. Here in New York, it’s on WNYC. It airs twice – at 8:40 and 10:40, and goes for about seven minutes.

BN: You’re doing this live? With people calling in?
It’s actually taped on Friday. And at the end of the segment, there’s a challenge puzzle. People send in their answers either by regular mail or Email. One person who’s correct gets chosen to be on the air the next week. On an average week, we get 500 to 1200 people sending in answers. We’ve had as many as 2,000. Those are people who want to play on the air.

BN: And what’s a typical game like? Oh, now you’re going to test me …
Okay. This is a puzzle called “2D.” Every answer is a two-word phrase or name in which each word begins with the letter “D.” For example, if I said, “See a movie as a foursome,” perhaps, you would say …

BN: Double date.
Right. Number one - first two words of an entry in a personal journal.

BN: These are all with D’s?

BN: Say it again?
First two words of an entry …

BN: Dear Diary.
… is correct. Number two – transaction that’s final. You’d say that’s a …

BN: No idea.
Done deal.

BN: Oh.
1967 film about twelve World War II prisoners …

BN: The Dirty Dozen
… is correct. Make a long-distance call without operator assistance.

BN: Direct Dial.
… is correct. Where to stick a floppy?

BN: Uhm … something disk – disk drive.
Disk drive is right. Sultry part of a summer.

BN: Dog days.
… is correct. Basketball no-no.

BN: Double dribble.
… is right. Brand of mini-vac.

BN: What’s a mini-vac?
Mini vacuum cleaner.

BN: Oh, I don’t do any house cleaning.
[Office intern]: Dirt Devil
Dirt Devil is correct. 1973 Number One hit for Helen Reddy.

BN: Helen Reddy?
[Intern]: “Delta Dawn.”
“Delta Dawn” is right. Villainous sailor in “HMS Pinafore.”

BN: No idea.
That’s a tough one – Dick Deadeye is the answer. 1967 Rex Harrison film role.

BN: Dr. Doolittle.
… is right. One who avoids military service.

BN: Draft dodger.
Excellent. Place for ship repair.

BN: Dry dock.
… is right. Batman and Robin, with “the.”

BN: Dynamic Duo.
… is correct. 1983 movie with Jennifer Grey and Patrick Swayze.

BN: Dirty Dancing. Terrible movie! Do you let people editorialize?
Why not? Fancily-dressed guy.

BN: Dapper Dan.
… is right. And your last one – something contestants bet on in Jeopardy.

BN: Daily Double.

BN: I had a sagging middle because I was nervous.
You passed.

BN: Now can we talk a bit more about what you do?
I get puzzles from all over, and my job, first of all, is to pick the best puzzles and to work with constructors so they produce their best work and send me their best work. After I accept a puzzle, I may fiddle with the grid in a little spot. I don’t like stupid obscurity. If there’s a clue like “50-mile river in Rumania,” in an otherwise terrific puzzle, I may rework a corner to get rid of that.
Once a puzzle is accepted, then I edit the clues. I have to make sure they’re accurate, number one, and make sure they’re the right level of difficulty. And I try not to repeat anything I’ve used recently. Try to make it interesting, fresh, maybe funny once in a while.

BN: Do you have a favorite puzzlemaker?
I have several. There’s one here in the city David Kahn, who’s superb. Frank Longo is exceptional. He’s a young music instructor in Pittsburgh.

BN: So what are these people doing besides making puzzles?
Absolutely everything. They’re teachers, computer people, writers. David Kahn is an accountant. Randolph Ross is a high school principal.
BN: Doesn’t The Times sponsor some kind of Puzzle-Off think once a year?
WS: Well there is an annual championship, the American Crossword Puzzle Tournament. It is an even that I founded in 1978 and have directed every year. This year will be the 21st annual.

BN: How many people participate? Are they all sitting at big tables with puzzles in front of them?
We had more than 300 last year. And it does have the touch of an SAT in it. It’s held in a huge hotel ballroom. Contestants sit at tables separated by dividers, so no one can cheat, although I don’t think anyone would.

BN: That’s the great thing about crossword puzzles – you’re playing against yourself. It’s just you and your brain.
Right. And people race to solve the puzzles. They get 15 minutes for a small one. Up to 45 minutes for a big one. You get points for accuracy and speed. And in the final round, there’s a puzzle conducted on stage, on giant Plexiglas boards for the top three people, for everyone to watch. It’s a real good show.
BN: Besides the tournament or running into people on line in the supermarket, do you have some sense of your audience?

Surveys have shown that about 27 percent of newspaper readers do the crossword – so that’s a lot of people. And I recently heard that one percent of Americans name crosswords as their favorite thing to do. That’s just an incredible number of people.
And there are all types. For The New York Times, it’s an educated, cultured audience. It tends to be a little older than average, because that’s The Times readership. But they are people with a good sense of humor, I think. The sort of person who can look at a clue and if you get stuck in a puzzle, be able to backtrack and then plunge in ahead and get the answer. You’ve got to have a flexible mind.
BN: Sometimes, because of the cleverness of the clues, you really have to see that a word or phrase can have a second meaning. There’s often a lot of wordplay.
WS: Well, here’s an example. It’s in a puzzle that’s coming up. The clue is “Sales pitch.” And the answer is “pie.”

BN: Soupy Sales.
One of my testers worked out the answer from the crossing letters and still had to stare at it for five seconds before he slapped his head. I try to do lots of that.

BN: Do you know the history of the crossword – when it first started?
It was invented by Arthur Wynne. And the first one appeared in The New York World, December 21, 1913. I’m the only person I know who owns an original copy of that puzzle. And it’s good to mention it right now, because the Post Office has just issued a stamp to honor Arthur Wynne and the invention of the crossword. The front of the stamp shows a little bit of Wynne’s first puzzle, with a hand filling it in, and on the back will be an explanation of who Wynne is. I was a consultant on the stamp.

BN: Was there a puzzle in The London Times before 1913, or is this really the beginning?
This is the first one.

BN: So it’s really an American invention?

BN: Have you had a favorite puzzle lately?
Several. One was a daily puzzle which appeared on Election Day in 1996. The clue for the middle answer across was, “Lead story in tomorrow’s newspaper.” That was the clue on Election Day. And it appeared that the answer was “Clinton Elected.” However, because of ambiguities in the down words of the first seven letters, you could also fill in “Bob Dole Elected.” Either one fit.

BN: Sounds like “Dewey Defeats Truman.”
We were covered on both sides, not as if there was a whole lot of suspense in that election. But the clue for the first answer coming down was, “Black Halloween animal.” And it could be either “bat” or “cat.” So the “b” was the “b” of Bob Dole, and the “c” was the “c” of Clinton. And all the next sets worked like that.
Well the day that puzzle appeared, I immediately started getting calls from solvers who were outraged that I would be so presumptuous to assume that Clinton would be elected. And I also had calls from people who filled in “Bob Dole Elected,” and thought that I had made a colossal mistake. So that was one fantastic puzzle.

BN: So what do we have to look forward to next Sunday and the Sunday after?
I just try to have a new idea every week, and something that’s going to twist your brain.

BN: I believe that doing crossword puzzles is great exercise for your brain. More people should do them.
Studies from psychologists have shown that crossword solving staves off Alzheimer’s Disease. It keeps the mind sharp and it’s just good training for the mind. And if it helps for older solvers, it has to help for all of us.

© index magazineWill Shortz
Will Shortz by Matt Petosa, 1998
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