Interview with Will Shortz: UVA Law Grad, Puzzlemaster, Ping-Pong Aficionado

Bitter Success Interviews, Lawyer

Will Shortz graduated from the University of Virginia School of Law. But he always knew he had a higher calling—or should we say callings: New York Times crossword puzzle editor, puzzlemaster of NPR’s “Weekend Edition Sunday,” star of the hit documentary “Wordplay,” ping-pong aficionado, and real life Riddler. Also, he has brought great joy to President Bill Clinton. He was kind enough to take a few minutes to chat with us.

Did you ever work in law?

No law work at all. Near the end of my third year at law school, the head of the placement office noticed I had never had a single interview. She called me in because she was concerned. She asked what my plans were. I told her I had a job. I could see her face brighten. She asked me who I was going to work for. I told her Penny Press, which was one of the major crossword magazine companies. I’d worked there as a puzzle editor during all my law school summers, and I was going there full-time after I graduated. I watched the placement lady write down in her book: “Penny [comma] Press [comma]” … waiting for the rest of the law firm’s name.

Hilarious. So why did you go to law school in the first place?

My dream was always to have a career in puzzles, but I thought that would mean a life of poverty. Generally speaking, puzzles don’t pay well. It’s very difficult to make a living creating puzzles.

I graduated from Indiana University in 1974 with a self-designed degree in Enigmatology, the study of puzzles. That summer I interned for Penny Press, and that let me see how I could have a legitimate career in puzzles — by being an editor. My plan was to practice law for 10 years and to make enough money to retire and do what I really wanted.

I found law school a bore, though. So in the spring of my first year I wrote my parents that I would be dropping out at the end of the semester. You can imagine how that news went over. My parents strongly recommended that I complete my degree and then do what I wanted. That seemed like good advice, so I stayed.

Knowing that I wouldn’t practice law after graduation was liberating, and I studied whatever I wanted. For example, I took a couple of courses on intellectual property, including writing a paper on “Copyright Protection for Puzzles and Games,” which has been useful in my career. I never took a single course on trial practice or litigation.

I don’t regret law school at all. It’s great training for the mind. It teaches you to take a complex issue, analyze its parts, and deal with each one individually. It also teaches you how the world works. And it confers respect. If my only college degree had been in puzzles, I don’t think people would take me as seriously as they might knowing that I also have a J.D. from a prestigious university.

How did you get into puzzles?

I had been making puzzles since I was 8 or 9. I sold my first one at 14 to my national Sunday school magazine. It wasn’t a crossword, but something I’d invented. I became a regular contributor to Dell puzzle magazines when I was 16. So I’ve always been into puzzles.

How long does it take to create a crossword puzzle?

It varies according to the size of the puzzle and the difficulty of the construction. On average a daily New York Times crossword takes 4-6 hours for an experienced constructor to make. A Sunday puzzle might take 6-20 hours.

I should point out I am the editor of the Times puzzles, not the creator. The puzzles are made by freelance contributors around the country.

What does that mean, what is your role?

That means I select my favorite puzzles from those submitted to me. I get 75-100 submissions a week. I can publish only seven, because there is one puzzle a day. So the competition is fierce.

The biggest part of the job is looking at the mail and corresponding with the contributors, telling them what I like and don’t like. Everyone gets a response.

When I edit a crossword, it’s hands-on work. On average about half the clues in the Times crossword are mine. Everything has to be accurate, of course. I also edit for freshness, humor, occasional twistiness, and a level of difficulty appropriate for the day of the week.

You also do crossword tournaments. What is a crossword tournament like? Are there national teams?

I direct the annual American Crossword Puzzle Tournament. It’s an event I founded in 1978, when I was 25, and I’ve directed it every year. It’s the world’s oldest and largest crossword event. We have around 700 contestants each year and total attendance of around 1,000.

I also founded the World Puzzle Championship in New York in 1992. The WPC is held in a different country every year. It will be in Eger, Hungary, this fall. The WPC puzzles are not crosswords, because the competitors speak many different languages and come from many different cultures. So we do sudoku, Ken-Ken, and all sorts of logic, math and visual puzzles, so that everyone can compete equally no matter where they’re from.

What countries are the best?

So far the U.S. is the best. We’ve won the championship more than anyone else, 12 times in 19 years. The Czech Republic and Hungary are also very good. Japan and Germany have had strong teams lately.

Do you ever compete?

I’ve competed in a crossword tournament only once. Mostly I direct puzzle events. But in 1979 I competed in a crossword marathon in Cleveland, Ohio. It was sponsored by a bookstore. They offered $1,000 for solving one really big, really hard crossword over 24 hours. You could use all of the books in the bookstore to help you. Obviously, this was before the Internet. I was the first to finish the puzzle, in 9-1/2 hours. I won the $1,000. So now I’m officially retired from competition — undefeated!

When people think puzzles, your name is pretty much synonymous with puzzles. Are you the greatest puzzle solver in the world?

No. I think I’m good at making and editing puzzles. As a solver, though, I’m just average.

Can you give me a tip?

For the Times crossword I recommend starting with the Monday one, because that’s the easiest one of the week. Fill in what you know for sure, and then use those letters to get the crossing words. Focus on the rarer letters of the alphabet, which are more helpful than the common ones. If you get stuck, don’t be afraid to guess. But also remember that a guess may be wrong, so don’t be too reluctant to erase and start over.

Any celebrities do the New York Times puzzles? Does President Obama ever email asking for hints?

I’m not aware that President Obama solves puzzles. But I have gotten a couple of letters from Bill Clinton, who is a big crossword doer. He wrote me a beautiful note on my 50th birthday telling me that the New York Times crossword is the one thing in the newspaper that is guaranteed to give him a good feeling.

That’s awesome.


You’re also a big sudoku guy. I understand you have the top-selling sudoku books. Is there a rivalry between crossword people and sudoku people? Are they two distinct types of people, or is there a lot of overlap?

They tend to be two different groups. The crossword people like to have their knowledge and vocabulary tested. With sudoku you don’t have to know anything. It’s a pure logic challenge. I’m in the minority. I love both puzzles. Of course, I like almost any kind of puzzle.

Do you have a preference, though?

I’m better at word puzzles.

I understand you have quite the collection of puzzles?

I own well over 20,000 puzzle books and magazines dating back to 1542, I believe it’s the world’s largest library on the subject. My oldest book is a collection of riddles in Latin, published in what is modern-day Germany.

I also have the only known copy of the world’s first crossword in private hands. It was published in the New York World in 1913. I have lots of good stuff.

Is there some order of puzzle masters? Have you ever met the previous generation’s puzzle master? Do they confer wisdom down through generations?

I was the first person to have the title “puzzlemaster.” That was conferred on me by Liane Hansen at NPR. My hero growing up was the puzzlemaker Sam Loyd, who lived over a century ago. His puzzles appeared in newspapers and magazines across the country. He was a genius at creating very hard puzzles that nevertheless had wide popular appeal. When I was a kid I got books of his, and I was crazy about him. My desire for a career in puzzles is probably due more than anything else to him.

Tell me about feature documentary “Wordplay,” from 2006, of which you are the focus.

The director of the movie, Patrick Creadon, left a message on my answering machine at the Times, saying he and his wife, Christine O’Malley, were fans of the puzzle, and they wanted to do a documentary about me. He asked if I would be interested. I said sure, what the hell. I thought this would be something that might appear eventually on late-night cable TV. So they got to work, and it turned out to be something really great. It was shown at the Sundance Film Festival, picked up by IFC Films, and released in theaters. It ended up being much bigger than I’d anticipated. It became one of the 25 highest-grossing documentaries of all-time. According to Rotten Tomatoes, it was the best-reviewed documentary of 2006. They gave me a Golden Tomato award for it.

I didn’t know about the Golden Tomato. Tell me about your TV appearances.

I guest-starred on “The Simpsons” in 2008. That was cool. Just my voice, of course, with a cartoon image of me. I was also on “How I Met Your Mother” in 2010, where I played myself at a snooty New York City party. I had to join the Screen Actors Guild to do that show.

I read that you were named one of “The 100 Best People in the World” according to Esquire magazine, back in 1997. That’s gotta be a pretty nice feather in the cap?

Well, Homer Simpson and Jack Kevorkian were also on that list, so it was an interesting group to be a part of.

Quite the diverse list. Let’s talk ping-pong. I understand that’s a big part of your life.

I’m fanatical about the game. Growing up in Indiana I had a ping-pong table in the family recreation room. So I played a lot as a kid. I have trophies from junior high and high school. In 2001 I found a club near my home in Westchester County, N.Y., where I live, that played two nights a week. I joined up. Soon the club expanded to three nights a week, then four nights, then five, and eventually six. I sort of became the club’s director. In 2006 Robert Roberts, a three-time champion of the Caribbean, joined the club. He became my coach, and we became good friends. We started dreaming of opening our own table tennis place, where we could play as often as we wanted. This dream came true in May, when we opened the Westchester Table Tennis Center, in Pleasantville. There are 18 tables, more than 13,000 square feet, a new gymnasium floor, excellent lighting, and a high ceiling. I believe it’s the largest dedicated table tennis space in the country. In three months we have almost 200 members. We’re averaging 40-50 players a day.

Can anyone come by?

Yes. The club is open seven days a week. It’s $10 a day for adults, $7 for kids. People can play as long as they want. Membership is $350 for adults, $175 for kids. I’m there literally every day. More information is at westchestertabletennis.com.

Three things you can’t live without?

1. iPad
2. iPhone
3. A pen

Book you’re reading right now?

I don’t think I’m in the middle of anything right now. But I’m an avid reader of The New Yorker and the news.

Advice for someone who wants to get into the puzzle world?

Start making puzzles. If you’re into crosswords, check out Cruciverb.com. It has resources and advice and a community that will help with construction and explain how and where to submit puzzles for publication. Also, consider joining the National Puzzlers’ League, which is the world’s oldest puzzlers’ organization. Information on that appears at www.puzzlers.org.

I almost forgot to ask, is it true you wrote the riddles for a Batman movie?

Yes, for “Batman Forever.” The producer called me after filming had already started. They needed four riddles, and none of the writers had any idea how to write a riddle. The only constraint was that each riddle had to contain a number somewhere in it. Here is my favorite. Are you ready?

We are five little things of an everyday sort. You’ll find us all in a tennis court.

Wait, don’t tell me (60-second pause). OK, I give up, tell me.

I wouldn’t expect anyone to get this off the top of their head. The answer is the five vowels. They’re everyday things, and they’re all found literally in the phrase “a tennis court.”

If you think about it, they should have had you play the character, you’re the real life Riddler.

I guess I am.

Photograph by Donald Christensen

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