Word Puzzle Guru Will Shortz

With a Bic, for Confucius

He’s one of those guys who opted for the create-your-own-major option in college, graduating with a BA in ‘Enigmatology,’ the study of puzzles. After completing a law degree, he decided law wasn’t enough fun and launched a career in puzzle-making instead. He describes himself as ‘playful,’ and when he talks about puzzles, he sounds like the enthusiastic yet humble ambassador of a friendly foreign country. Meet Will Shortz, the puzzle master for NPR’s Weekend Edition Sunday, crossword editor for the New York Times, former editor of Games magazine, subject of the 2006 documentary film Wordplay, and founder and director of the American Crossword Puzzle Tournament and the World Puzzle Championship, to name a few of his titles. In advance of his Campbell Hall appearance, he spoke to me last week about the skills behind puzzle-construction, why crosswords encourage well-rounded living, and how Bill Clinton exemplifies the modern puzzle-junkie.

Have you always been a puzzle solver? It’s probably hard from the inside to explain how your mind works, but how do you see the interrelations between words?

Click to enlarge photo

I made my first puzzle when I was 8 or 9, and looking back I see lots of indication that this was the perfect career for me. I remember in 1st grade we had a lesson about compound words, and we had to circle all the compound words on a page, like ‘highway.’ Well, my list had twice as many words as everyone else’s, and the teacher was amazed, and when I showed her my paper, I had taken words like ‘home’ and broken it down into ‘ho’ and ‘me.’ Clearly, I hadn’t totally understood that there needed to be a relationship between the parts.

One of the things I loved to do was study maps, and make lists of the highest mountains in the country. And I would take a word like Crawfordsville-I grew up in Crawfordsville, Indiana-and I would find as many words in it as I could. I’ve always been good at anagrams. I can generally solve a jumble puzzle in 6 to 10 seconds.

Wow. I wish I could say that. So, you went to law school, but decided law wasn’t creative enough, for you huh?

No, I consider myself as playful kind of person, and playful is one of the last adjectives you would ever apply to law. I’d say it was good training for me. First of all, it’s good training for the mind. To be a good lawyer, I think you have to be able to take a complex issue, break it into its component parts and solve them-law is a kind of problem solving. Secondly, it was good for me just as a learning experience in business and how the world works. I’m an independent sort of person-I run crossword competitions, I write and edit books-so those skills have come in useful. And third, since my undergraduate degree was in puzzles, I’m not sure how seriously people would take me if I didn’t have a law degree to my name.

And you want to be taken seriously, despite being playful?

Yeah, Why not?

In your work for the Times, you’re not actually constructing the puzzles, you’re editing them, right?

As a puzzle maker, I make puzzles for NPR that are aired every Sunday, I make them for Reader’s Digest, and I do some for the Sunday New York Times puzzle page. Those ones aren’t crosswords, they’re novelty puzzles-puzzles I create myself. Back when I was editing Games magazine, I had puzzles in every issue. But at the Times, my job is to edit the puzzles, working with puzzle-makers to get them to create their best work.

What's your favorite puzzle?

See the results without voting.

So the crosswords we play in the New York Times are constructed entirely by freelancers?

That’s right.

How many such puzzle-makers are there out there?

I publish about 110 puzzle-makers a year. Hundred and hundreds more try.

What makes for a good crossword constructor?

Number one, you have to spell well. I just got a puzzle from a prominent puzzle-maker that had the word ‘chieftain’ spelled with an on. You also have to know about a lot of stuff. Nowadays, crosswords are filled with everything-from all the old standards like history and geography, to TV, movies, and rock and roll. It helps to have a playful turn of mind, especially because crosswords tend to be thematic, so that the long answers come together in an amusing way. Constructing a grid is a peculiar skill that only a few people have. And writing good clues also helps. I don’t worry so much about a puzzle-maker’s ability to write clues, because if the grid comes together really well I can do that part, but it’s always great to find someone who can do it all.

I find it interesting that until you took over at the Times, the names of the crossword contributors weren’t even printed in the paper. I think I’d find it tough to keep on writing if I didn’t get a byline.

Yeah, the daily paper never printed them until I took over. When I was interviewed for the position in 1993, they asked what I would do differently, and that was the first thing I said. It was deserved, and I also knew I would get better puzzles if I did that, because people would take more pride in their work.

Some people seem to be able to dabble in puzzles-I probably shouldn’t admit it, but I’m happy to leave a crossword half-finished-while others get absolutely obsessed with them. I think of the characters in the Scrabble documentary, Word Wars, as examples of puzzle fanatics. What do you think that compulsion is about, and can you relate?

Word Wars was devoted to the Scrabble elite-these were not normal people. Yes, puzzles can become an addiction, and up to a point I think it’s a healthy addiction, because they strengthen your mind, inculcate mental flexibility, and build your sense of humor. But of course you can go too far. I’ve found that to be a great crossword solver, you need to know a lot about everything, so it encourages you to get out there and live, and become well-rounded. My experience is that it’s often the busiest people who make time in their life for puzzles, though you imagine the opposite. Bill Clinton is a perfect example; you could hardly be a busier person, and yet he does lots of puzzles. I think it’s because crosswords are a great break from other mental activities. You’re focused on whatever problem you have in life and you need to take a break, but your mind is still going. If you turn to a crossword, you can return to the original work relaxed, refreshed, and renewed.

You sound pretty convinced!

Yeah, I do like to promote puzzles.

How about the Sudoku craze? I don’t completely understand the appeal of that type of logic the way I understand the satisfaction of solving word clues. Do you think crossword lovers are switching over to Sudoku?

No, I don’t think they’re switching over-I think Sudoku is bringing a whole group of people into puzzling who weren’t into it before. My sister is a good example. She could never really get into crosswords, and she’s really very intelligent, but she just wasn’t that interested, or very good at it. But she’s crazy about Sudoku-fanatical about it. Crosswords and Sudoku share one thing, in that in both puzzles you fill in empty squares. I think that as human beings we like to fill empty spaces. Crosswords connect to real life; you have to know things. With Sudoku, you don’t have to know anything, but you have to use logic, and that’s a different skill. I’m the sort of person who loves both. I know that if I let myself go I’d become a Sudoku fanatic, too.

Going back to Bill Clinton, your famous clue from election day, November ‘96, ‘Lead story in tomorrow’s paper,’ and the answer, which worked either as ‘Clinton elected,’ or ‘Bob Dole elected,’ are clearly the sign of a comic-even mischievous-streak. I imagine you as one of those kids who told a lot of jokes in school, maybe even practical jokes. Did you?

Not practical jokes-there’s a little mean streak in a practical joker, and that’s not the way I feel-I feel playful instead. In junior high and high school, when a test was coming up in class, I would often write my own test as if I were the teacher, and give it to my friends.

I was born in ‘52, and Jeopardy came on in ‘63 or ‘64-I was a big fan, and I’d create boards for my friends and family. I’ve always said puzzles are a kind of long distance entertainment. They’re not like standing on a stage singing, acting, or playing a piano. My form of entertaining is creating a puzzle or a game, usually in print, and the feedback comes in a lot later.

It seems like that goes along with the solitary activity of puzzle-solving. Do you enjoy speaking to large groups on tour, the way you’ll be appearing in Santa Barbara?

In-person talks have become natural, and I do enjoy them now. I grew up on an Arabian horse farm in Indiana, and I’m naturally a shy person, so the idea of standing in front of hundreds of people and speaking about a solitary activity is oxymoronic. I don’t talk for the whole 90 minutes, though. I give a short presentation on the history of puzzles, how you make them, and some of my favorite puzzles and puzzle-makers. Then I spend about 20 minutes answering questions, and then we do audience participation word games. It’s that part that I always enjoy the most. I find puzzle people tend to be interesting, smart, well-read, amusing people, and I guess I particularly enjoy an experience like this because it gives me rare personal contact with the people who actually do my puzzles.


Will Shortz will speak at UCSB’s Campbell Hall, Sunday May 6th at 4pm. Books will be available for purchase and signing. For tickets, call 893-3535 or visit

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