Party Down: 100 Years of the Crossword Puzzle

A conversation with Deb Amlen, New York Times crossword puzzler extraordinaire.

Rebecca J. Rosen / Dec 20 2013, 7:32 AM ET

This weekend marks the 100th birthday of the crossword puzzle. On December 21, 1913, Arthur Wynne published a little diamond-shaped grid, along with 30-odd clues, in the New York World. The puzzle didn't immediately catch on, but just over a decade later, it exploded.

In 1924, the publishing house Simon & Schuster, agreed to a small (3,600-copy) run of a crossword puzzle book, prompted by founder Richard L. Simon's aunt, who wanted to give such a book to a friend. It became "a runaway bestseller." According to Smithsonian Magazine,

In no time the publisher had to put the book back on press; through repeated printings, it sold more than 100,000 copies. Soon a second collection followed, and then a third and a fourth. In 1924 and 1925 the crossword books were among the top 10 nonfiction bestsellers for the year, besting, among others, The Autobiography of Mark Twain and George Bernard Shaw’s Saint Joan.

In the time since, crossword puzzles have become a beloved morning tradition in many homes. Today's puzzles still fundamentally look a lot like that first puzzle by Wynne, but many aspects of puzzling have changed: how they are constructed, the sorts of clues they contain, and even how (some) puzzlers go about solving them. I spoke with Deb Amlen, writer of Wordplay, the official crossword blog of The New York Times, and humor columnist for Yahoo! Tech, about how our digital age is shaping crossword puzzles. A lightly edited transcript of our conversation (which was conducted in Google Docs) follows.

So perhaps we can just begin with a little bit of the basics. How do crossword puzzles get put together today? Are writers using software? Graph paper? What does the process look like?

Well, everyone is different, of course, but I would say that the vast majority of constructors use some sort of software to at least frame their crossword puzzle. By framing, I mean that although the idea for the theme or some of the really lively entries might be a result of their own creativity, the software gives them a cleaner place to store their ideas and build on them. And I would say that many constructors also fill their puzzles with words and phrases "by hand," even though they are using this software. Many of the software programs have an "autofill" feature where the computer puts in words just because they fit, but that’s frowned upon in the community. The better puzzles have lively entries that constructors save in word lists so that the puzzles are more entertaining.

I created my first crossword puzzles on graph paper, and when I finally purchased the software in 2004, I really did see the advantage of having a place to store my word lists, and not have to deal with the intense amount of erasure and bloodshed that building a puzzle involves.

So, just to make sure I have this straight, the software gives you a grid, and then you begin by filling in words to make everything fit. Once the solution is there, you write the clues?

This is a very simplified breakdown of how to build a puzzle, which not everyone follows.

1. First, you need to decide if you are making a themed or nonthemed puzzle. For the sake of this discussion, let’s say it has a theme. The theme can be anything, but in an early week puzzle, it usually is just a set of entries that all have something in common, something that makes them hang together. This is the part that really takes a lot of time if you’re a good constructor, because it’s a creative endeavor that also has quite a few constraints on it: You need to come up with something entertaining, that hasn’t been done before, that makes sense to/is likely to be familiar to a majority of solvers, and it also has to fit into the grid using certain letter counts, because a majority of puzzles use what’s called rotational symmetry. That’s a complex phrase that simply means that it’s symmetrical on a diagonal, and if you turn the grid upside down, it will look exactly the same. Those constraints have been in place for a very long time.

"I think that having software available for constructing has made it possible for people to be more prolific, although whether that’s a good thing is left for better minds than mine to determine."

2. Once you are happy with your theme, it’s time to build the grid. When you open a new file in one of these software programs, you can choose from a selected list of already built grids (e.g., they already have a pattern of black squares in them) OR, and this is the way professionals do it, you select a blank grid that is the size you want, and start to place your theme entries in the grid, placing the black squares at the same time. The challenge here is to place them so they don’t violate the constraints that need to be followed, but at the same time, giving the constructor a good chance of being able to fill around the theme with sparkling, lively entries. As you can see, it’s quite a challenge and an artform, but we’re not done yet.

3. Now it’s time to fill. There are some things that can’t be avoided when filling a crossword puzzle, but we generally try to avoid using too many abbreviations (and when we do, they should be ones that are instantly familiar to a majority of people, like NAACP or CGI) and too many "partials," which are parts of phrases like IN THE, which might be the answer to a clue like "The farmer ____ dell."

Will Shortz, who has been the editor of The New York Times crossword puzzle since 1993, is known for having brought the puzzle into the "modern age" by allowing more pop culture and lively entries into a puzzle that had been considered an activity in intellectual snobbery up to that point. I agree. I think the puzzle should be a form of entertainment. That’s why it’s located where it is in the printed paper.

4. Cluing time! This can either be fun or drudgery, depending on who you ask. I love writing a good, misdirected clue, and solvers who have some experience love that feeling of having to get into the brain of the constructor and editor.

Early in the week, the clues are pretty straightforward, and increase in difficulty as the week progresses. The editor is responsible for making sure that the clues fit the day of the week, are clear and play fair with the solvers, and are generally well-written. There are tricks that the constructor uses to let the solver know that something else might be going on rather than it being a straightforward clue. For example, if you see a question mark at the end of a clue, that indicates that some wordplay is involved.

In what ways has software changed that process? Do you see any differences in puzzles that are built with software versus ones done by hand?

I think that having software available for constructing has made it possible for people to be more prolific, although whether that’s a good thing is left for better minds than mine to determine. Personally, I don’t like puzzles that rely on the pre-programmed words and phrases and seem to be just churned out, although I know it exists. You can hit a button that says “autofill,” and if the grid is fillable, it fills.

"If you have to Google something to help you complete the puzzle and you learn something from having done it, that’s a good thing."

But that doesn’t make it a good puzzle. And it’s very obvious when someone has done that. You can have words in there that are not only not commonly used or are of interest to the average solver, but they might not even make sense. I would much rather see constructors who take the time to create or “handfill” a puzzle with current words and phrases that are of interest to people today. Or at least, if they’re not current or within my own knowledge base, they are “gettable” through the crossings, and make me feel interested in learning about them. I always love learning new words, but there has to be a valid reason for it being in the puzzle.

Getting away from the question of crossword construction, do you think technology—particularly the web—is changing the process of solving puzzles for people?

Oh, yes. While there are many solvers who continue to solve in the print paper and in books and magazines like Games Magazine, the online solving community has exploded. People are solving on the web, on their tablets, on their phones … anywhere and anyway they can get a fix. And I think that some people, who are called speed solvers and who like to time themselves to see how fast they can solve, like solving on a computer, because most of them can type faster than they can write.

I see so many sites where you can look up clues if you are stumped. I was just wondering the other day if calls to the Times’s clues hotline had fallen off a cliff.

Yes, Googling a clue has gotten very popular, although there are a significant number of solvers who consider that “cheating.” I, personally, don’t think it’s cheating unless you’re competing in a tournament. As Will Shortz says, it’s your puzzle; you can solve it any way you want. And I think that if you have to Google something to help you complete the puzzle and you learn something from having done it, that’s a good thing.

What is the impact of blogs like Wordplay on puzzlers? Are puzzle-lovers connecting to each other more? Is there more of a community?

I’m so glad you asked that. Yes, there’s a huge online community, and Wordplay is just part of it. Some people feel that doing a crossword puzzle is a solitary activity, and while it can be, I believe it has the potential for tremendous social interaction.

"She confessed that solving the puzzle was the last lucid conversation she had with him before he died. I cried when I read that."

Just the other day, in fact, I was watching a television show where a woman wanted to know how to look more available to men when she was out, and the suggestion was that she bring the crossword puzzle with her and strike up a conversation with someone by asking them for help with a clue.  Puzzles bring people together. I remember spending time looking over my father’s shoulder when he did the Times crossword, and was so pleased when I could finally help him solve some of the clues.

The most moving connection I can recall about how puzzles bring people together is this: I wrote the crossword puzzle for BUST Magazine from 2005 and until this year, and someone once wrote and told me that she took the puzzle with her to do on the plane when she went to see her dad on his death bed. They had always gotten a kick out of doing the BUST puzzle together, because it was much different than what you would see in a New York Times crossword. She confessed that solving the puzzle was the last lucid conversation she had with him before he died. I cried when I read that.

Prior to Wordplay, The New York Times had a very busy online forum where people could talk about the puzzles, and in addition to the Wordplay blog, we also have popular blogs like Diary of a Crossword Fiend, written by Amy Reynaldo and Rex Parker Does the New York Times Crossword Puzzle, written by Michael Sharp. All are places where people get to talk about the day’s puzzle.

What I love about writing Wordplay is watching friendships evolve. The commenters on Wordplay seem particularly tight. After a natural disaster, one of my regular readers lost a good number of her possessions, and people wrote asking me how to help her. On a crossword blog in a newspaper. That just blows me away and makes me feel very good about being a part of it.