A Puzzlemaster's Tale: An interview with Will Shortz
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On today's episode of the 5 Things podcast: For nearly half a century, Will Shortz has left a lingering mark on the the world of crossword puzzles. After starting his career at Penny Press and Games magazine, he was hired by the The New York Times in 1993 where he still works in 2023. He's also known as NPR's Weekend Edition's Puzzlemaster. He and 5 Things Sunday host James Brown discuss his life, work, and the world of puzzles.
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Hit play on the player above to hear the podcast and follow along with the transcript below. This transcript was automatically generated, and then edited for clarity in its current form. There may be some differences between the audio and the text.
James Brown:
Hello and welcome to 5 Things. I'm James Brown. It's Sunday, February 19th, 2023. Every week we take an idea or concept and go deep, and this week we're talking about puzzles.
One of the things that truly fascinates me is small groups of people who do truly unique things. A member of one of those groups is joining me today. His name is Will Shortz. If you're a crossword puzzle addict, you've probably heard of him. He's the longtime New York Times crossword puzzle editor and resident puzzle master at NPR's Weekend Edition. Shortz has made a living by making puzzles. That seems impossible, but it's true. What's that like, and how do you put together a puzzle anyway? We'll find out in just a few moments.
Will Shortz, welcome to 5 Things.
Will Shortz:
Thank you, James. Good to be here.
James Brown:
How do you feel about the term "puzzle master"?
Will Shortz:
Well, it's a nice term. It was given to me by Liane Hansen, who was a longtime host of Weekend Edition Sunday on NPR. And it's interesting, the epithet used to be, someone who's good in puzzles was the puzzle king, or maybe the puzzle queen. She called me puzzle master, now everyone calls themselves a puzzle master.
James Brown:
How many puzzle masters are there?
Will Shortz:
I'll tell you, I'm the only one with a college degree in the subject. I graduated from Indiana University with a major in enigmatology, the study of puzzles, and I'm the only person in the world still ever to have done this.
James Brown:
Wow. Whoa, whoa, did you create that, or was it there and nobody else just signed up for it?
Will Shortz:
So Indiana has a program called the Individualized Major Program. If you are accepted, you can major in literally anything, and I convinced them that puzzles were a serious field of academic inquiry. There were no existing courses on puzzles at the college, at the university, so I made them all up myself. One of them was Crossword Construction. I found a professor in the English department who would work with me, and every few weeks, I would go into his office with a new puzzle I had made, and sat by his side while he solved it and critiqued it. And that's how I made my first quality crosswords. I took courses on the history of American word puzzles of the 20th century, took courses on mathematical puzzles, logic puzzles, crossword magazines, the psychology of puzzles, and my thesis was on the history of American word puzzles before 1860.
James Brown:
I'm dumbfounded. I've never heard of this before. This is wonderful. Was it hard to assemble your own coursework in this world or what was it just a blast?
Will Shortz:
Well, it was a blast, yeah. So I made a list of all the subjects that I wanted to study in my major; logic puzzles, math puzzles, word puzzles, the history of puzzles. Before each semester started, I would find a professor in the most appropriate department who would work with me. So for math puzzles, it was a professor in the math department. For logic puzzles, I found someone in philosophy who would do it. For crossword magazines, I found a professor in journalism school who would do it. My advisor was in linguistics.
James Brown:
Wow. By all accounts, you decided on your profession way before then. Can you tell us how you came about that?
Will Shortz:
Well, I have been crazy about puzzle since I was a child. I started making them when I was eight or nine. I sold my first one when I was 14 to my national Sunday School Magazine. When I was 16, I became a regular contributor to Dell Puzzle Magazines. I used to joke as a kid that wanted to make puzzles for a living, never dreaming that it was possible. I tell you, in the 8th Grade when I was asked to write a paper on what I wanted to do with my life, I said I wanted to be a professional puzzle maker, but I'm the only kid in the world who has ever done this. So I went to Indiana, never expecting to major in puzzles, obviously, but Indiana is one of about a dozen schools in the country that has a program where you can literally major in anything, so I was very lucky to go there.
I still didn't think you could have a career in puzzles, so I went on to law school at the University of Virginia. I have a JD from there. In the spring of my first year at Virginia, I wrote my parents that I would be dropping out at the end of the year and going into edit crossword magazines. My parents convinced me that that was a really bad idea; I should complete my degree, and I thought they had good advice. So I did get my a JD from Virginia, of course then they wanted me to take the bar exam, and that was too late. Nope, I'm going right into puzzles, and that's what I've done.
James Brown:
When did your parents realize that it was a real career?
Will Shortz:
My mother was a writer, and so she was always supportive. She was a creative person. In fact, she was the one who showed me how to submit my puzzle manuscripts to publishers when I was a teenager. So I was very lucky to have my mother, because I don't think most mothers would even know how to do that. My father was a personnel director for R.R. Donnelley printing company, more of a corporate type. And for years and years, he always said puzzles are an avocation, not a vocation. So he thought this would make a nice hobby to be a lawyer or whatever ever else I wanted to do. But once I started the New York Times in 1993, he came around and said, okay. I got the sense that he was accepting me by that point.
James Brown:
Could you see yourself as a lawyer or any other profession?
Will Shortz:
It was a brief time when I was out of work, when I was in my 20s and I thought I might go into advertising copywriting, because I think of myself as a creative person and good with words, but fortunately I got a puzzle job shortly after that. I think I'm ideally suited to do puzzles. I love them. They're creative. I laugh all day at work. Playing with words is playing with the mind. And another thing I love about what I do is the people I come in contact with. Puzzle people tend to be smart, interesting, quirky, well-read, often funny people, and they're the people I like to be around.
James Brown:
Define puzzle people.
Will Shortz:
Define puzzle people. The word I like to use is quirky. We use our brains, and of course, puzzle people are all sorts. There's something like 60 million Americans solve crosswords at least occasionally, so you can't say that all puzzle people are one type. And there's people who like crosswords are a little different from the people who like Sudoku. Say, crossword people like to have their knowledge and their vocabulary tested. Sudoku people like to have their logic tested, and they're two largely different groups. I'm one of the rare types who love both. In fact, I love almost any kind of puzzle, but puzzle people use their brains. They tend to be smart, and creative, and often funny.
James Brown:
You said you were out of work for a bit. I'm guessing there's not a lot of crossword puzzle jobs, or Sudoku creator jobs. What's the market like, is it competitive?
Will Shortz:
One of the reasons I never imagined having a career in puzzles was I didn't think it was possible to make a living from creating puzzles. And that's very hard to do, because the pay for puzzles is not that great. For the New York Times, we pay $750 for a daily puzzle, $2,250 for a Sunday, but we publish only a few in the whole year. More than 95% of our submissions are rejected, so it's really hard to make your living from creating crosswords. Nowadays, I guess if you make a puzzle app that's really successful, you could make an income that way. It used to be if you were making puzzles, you had to submit them to magazines or newspapers, or write books, and it's really hard to make your living that way. But now you can start your independent puzzle website, and if you build a name for yourself and you have really good puzzles, people will subscribe, and that gets rid of the middle person. You can make your living from being independent.
James Brown:
How do you build a name for yourself? Are you talked about? Is there a puzzle Twitter?
Will Shortz:
Yeah, there's puzzle Twitter, probably multiple puzzle Twitters. I think the way to make a name for yourself, first of all, is to have some puzzles in the mainstream publications like the New York Times, and come to crossword tournaments, maybe join the National Puzzlers' League, I don't know, if you do good stuff, enough people are going to come.
James Brown:
Is creating puzzles something that can be taught? Is it a knack? What do you need to make them?
Will Shortz:
The skills involved in making puzzles vary according to the kinds of puzzles. Crosswords are one thing, variety word puzzles are a different thing. And of course, KenKen, Sudoku and logic puzzles are something else. And then there's all sorts of computer puzzles that you... online puzzles, digital puzzles you can do now. I think you have to be smart. If you're a crossword person, you have to spell well. It helps to know a little about everything in the world. It helps to be creative, have a lively mind. Those are some of the skills.
James Brown:
Do you begin a puzzle with a blank slate? Do you have a plan ahead of time?
Will Shortz:
Well, most crosswords have themes, so you certainly plan that in advance. The first crossword I ever had published was in the New York Times in, let's see, it was in 1975, so I would've been 23 at the time. Most daily newspaper crosswords are 15 by 15 squares. So I had three 15-letter answers. One of them was Planet of the Apes, monkeying around, and Sir Edward Gibbon. So those are my three 15-letter answers running across the grid, plotted my pattern of black squares, dividing up the grid in a way that I thought I could fill, and then I actually filled it. So that's how you go about creating a crossword.
James Brown:
Are you picking the themes, or are you given suggestions?
Will Shortz:
Everybody comes up with their own themes. Maybe if a friend gives you a theme, you can use it, but you're expected to submit a completed crossword to the New York Times or anywhere else.
James Brown:
Has it always been that way? Has it changed over your half century doing this?
Will Shortz:
That's a long time, boy. This year will be my 30th anniversary at the New York Times. Well, there are several big changes, as you can imagine. When I started at the Times in 1993, all the puzzles were made by hand. People had graph paper, literally graph paper and their dictionary to work with, and maybe some crossword reference books that would be helpful. For a list of 500 words with R in the second position, it would list them all together. Nowadays, basically everybody uses software with databases, and there's lots of different crossword databases consisting of words that have been used in previous puzzles, and then just other vocabulary from the dictionary maybe that hasn't been used yet. There's either even databases that are ranked, where every word, and phrase, and answer in the database has been ranked according to its desirability. So something that's fresh and lively... and very familiar to everybody would be rated highly. And something that is cross-wordy and boring would be rated low. And maybe some obscurity from the depths of the dictionary would be desperation only.
James Brown:
Define a fun crossword puzzle.
Will Shortz:
A fun crossword puzzle is one that has a new idea, that twists your brain in a fresh way, that would be what the theme would do. And then, the clues should be amusing, maybe a little twisty, make you think. You think of the clue leads you... initially makes you think of one thing, and then the answer turns out to be something else. Sort of like a joke, there's a little twist there. And if a puzzle can be filled with little twists like that, then it's going to be a popular puzzle.
James Brown:
Should they be hard?
Will Shortz:
I don't care about the difficulty of a puzzle. The New York Times crossword gets harder as the week goes on. So Monday is very easy and Saturday is very hard, and the slope of difficulty is quite steep. I think that most people... well, let me think about that. Even the Monday New York Times crosswords I say are easy-medium, they're not like 1st or 2nd Grade easy, but they're pretty easy. And then, see how far through the week you could go. Sunday is a bigger puzzle. It's usually at a Wednesday or Thursday level of difficulty, but it takes longer because it's a larger grid.
James Brown:
Is your approach different than others?
Will Shortz:
Well, my approach is different from my predecessor, who was 36 years older than me. The crosswords I edit, I think, and that I encourage constructors to submit, have more lively ideas, have more current things going on, because basically, you want anything going on in the world, and anything that might be written about in the New York Times, that's fair game for a crossword. There a lot more modern references than there are now than there were in the old days. And one little change I made that was a huge thing when I did it in 1993, but it's now standard everywhere, is that commercial names are fair game for crosswords. It used to be brand names weren't allowed, they were taboo, like Oreo, O-R-E-O. When that showed up in a crossword, it was always clued as the prefix meaning mountain, which you can find in the depths of the dictionary. But why would you clue Oreo as an obscure prefix when it's a cookie that everyone knows? That's just an example.
James Brown:
Yeah, that sounds just a little bit of stubbornness. Well, if I were to compare you and your style, and the style that you encourage to the next generation, what differences would I see?
Will Shortz:
Interesting. Well, I'm 70 years old now, but I try to stay young. I read a lot, I go to the movies, and so I feel that I'm current in the world. So I think that the puzzles that I edit and encourage won't change that much when I'm not around anymore. The crosswords are way better now than they were 50 years ago. I don't know how they can get much better, but maybe someone will try.
James Brown:
You've mentioned technology in a couple different ways in our interview so far. Are there other ways that it's affected your work?
Will Shortz:
Yeah, technology has affected my work in a number of ways. Up until two years ago, crosswords were submitted by mail. That's how I preferred them; they would come in on paper. It helped me to see the whole grid at once, and I would mark at things on the side of the grid, things I liked and things I didn't like. That's the way I like to work. But that made everything hinge on me in a sort of an old-fashioned... well, it was obviously an old-fashioned way of doing things. So about a year and a half ago, the New York Times switched to digital submissions. It used to be just me in charge of everything. Now the New York Times has... let's see, five. There is five editors. Six editors actually, and we look at the submissions, and we edit digitally. And then at the very end for print, the puzzles are converted to print.
James Brown:
What do you think of the next generation of puzzle masters, are there ones that you admire?
Will Shortz:
Oh boy, there is so much more talent now. When I started at The Times in 1993, I think I was the perfect person for the job. Now, there are any number of people who would make first class crossword editors. The puzzle world is way better now than it was 30 or 50 years ago.
James Brown:
Any famous last words?
Will Shortz:
No, I can't think of anything.
James Brown:
Will Shortz, thank you for joining me.
Will Shortz:
Thanks a lot, James.
James Brown:
If you liked the show, write us a review on Apple Podcast or wherever you're listening. And do me a favor, share it with a friend. What do you think of the show? Email me at jabrown@usatoday.com, or leave me a message at 585-484-0339; we might have you on the show.
Thanks to Will Shortz for joining me, and to Alexis Gustin and Shannon Rae Green for their production assistance. You can fill out as many crossword puzzles as your heart desires on puzzles.usatoday.com. For all of us at USA TODAY, thanks for listening. I'm James Brown, and as always, be well.
This article originally appeared on USA TODAY: A Puzzlemaster's Tale: An interview with Will Shortz
