How Far Away Are Computer-Generated Crosswords?

[Image courtesy of ESLTower.]

There’s no denying that computers play a large role in the world of crosswords today.

Some companies use computer programs to generate their unthemed crosswords, no human intervention necessary. Computer programs like Crossword Compiler aid constructors in puzzle design and grid fill, allowing them to build and cultivate databases of words with which to complete their grids.

And, of course, with those little computers in your pocket, you can solve all kinds of crosswords (like those in our Daily POP Crosswords and Penny Dell Crosswords apps).

Heck, computers are even getting pretty good at solving crosswords — just look at Matt Ginsberg’s evolving crossword program, “Dr. Fill.

An article in Smithsonian Magazine posed the question, “why haven’t computers replaced humans in crossword creation?”

The answer, as you’d expect, is simple: computers are just fine at plugging words into established grids and generating basic, unthemed crosswords.

But unthemed is the key word there.

When people think of The Los Angeles Times, The New York Times, The Chronicle of Higher Education, The American Values Club, The Crosswords Club, or any of the other well-respected crossword outlets in the market today, I doubt unthemed puzzles are what comes to mind.

And when it comes to creating themes, innovating, and playing with the conventions of crosswords in order to create puzzles that surprise and challenge solvers, computers simply don’t have the chops.

They might be able to solve puzzles, but as far as I can tell from my research, there’s no program out there capable of generating and executing a theme with any sort of wordplay element involved.

[Image courtesy of Crossword Compiler.]

There is an art to creating an exciting grid, an intriguing theme, or a new puzzle mechanic that solvers have never seen before. The creativity of constructors is truly boundless.

And, it seems, the potential for crossword grids is just as boundless.

Recently, Oliver Roeder of FiveThirtyEight challenged the puzzle fans in his readership to calculate how many different crossword puzzle grids were possible.

He offered the following conditions:

  • They are 15-by-15.
  • They are rotationally symmetric — that is, if you turn the grid upside down it appears exactly the same.
  • All the words — that is, all the horizontal and vertical sequences of white squares — must be at least three letters long. All the letters must appear in an “across” word and a “down” word.
  • The grid must be entirely connected — that is, there can be no “islands” of white squares separated from the rest by black squares.

Now, obviously, all of those rules can be violated for the sake of an interesting theme. We’ve seen grids with vertical symmetry, islands of white squares, and more. Heck, plenty of grids allow words to go beyond the grid itself, or allow multiple words to share puzzle squares.

[“Cutting Edge” by Evan Birnholz. A puzzle where answers extend
beyond the grid. Image courtesy of The Washington Post.]

But assuming these rules are standard, what total did solvers come up with?

None. They couldn’t find a total.

One solver managed to calculate that there were 40,575,832,476 valid 13-by-13 grids following the above conditions, but could not apply the same technique to 15-by-15 grids.

40 billion valid grids. For a comparison, there are 5,472,730,538 unique solutions for a 9×9 Sudoku grid, and I previously calculated it would take 800 years to use every possible 9×9 Sudoku grid.

Of course, that’s 40 billion 13-by-13 grids. The number of possible 15-by-15 grids must be orders of magnitude larger.

Consider this: There were 16,225 puzzles published in The New York Times before Will Shortz took over the NYT crossword. The current number of NYT crosswords in the XWordInfo database is somewhere in the neighborhood of 25,000 puzzles.

And they’re one of the oldest crossword outlets in the world. Even when you factor in the number of newspapers, magazines, subscription services, and independent outlets for crosswords there are these days, or have been in the past, we barely scratch the surface of a number like 40 billion.

Maybe by the time we’ve run through that many, AI constructors will have caught up.


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Let’s make our own crosswords!

Stumped on what to get the puzzle lover in your household? Well, if didn’t find anything in our Holiday Puzzly Gift Guide, why not make a special crossword just for them?

It’s the perfect do-it-yourself gift, and I’m happy to show you how! Welcome to PuzzleNation Blog’s How to Make a Crossword!

1.) The theme

The most important part of a crossword is choosing a theme. If you’re constructing with ambitions of submitting to the New York Times or the Los Angeles Times, you’ll need something inventive and tricky up your sleeve. 

But if you’re constructing for a friend or loved one, the theme is easy: make it about them!

Come up with your theme entries. For a gift puzzle, these could be hobbies, nicknames, favorite sports teams or TV shows, anything about them, really! Be sure to come up with several pairs of the same number of letters. (It’s a necessity when it comes to crossword symmetry.)

Choosing theme entries is often something done in tandem with choosing a grid, since word placement is a crucial part of building any grid.

For my example puzzle, I’m using a list of celebrity names.

2.) The grid

Constructing a grid from scratch can be tough, so I’d recommend first-time constructors check out sample grids. You can browse the newspapers until you find one that suits your needs, or you can let the Internet do the work for you! CrosswordGrids.com has a selection to choose from, for instance. If you’re using a construction program like Crossword Compiler, you can browse options for grids as well.

If you’re looking to start regularly constructing crosswords, I’d suggest building up a library of grids with various theme-entry lengths. (My personal grid library is organized by theme layouts, so if I have two 11-letter entries and two 10-letter entries, I can flip to a 10-10-11-11 in my folder.)

Here’s the grid I’ve chosen for today’s puzzle because it fit the theme entries I wanted. (Ignore the red box. That’s simply Compiler’s cursor.)

Now, I know all that white space to fill can seem intimidating, but placing the theme entries not only helps to guide the fill (the process of completing the grid), but breaks up that white space into manageable sections.

Here is the same grid with the theme entries placed:

3.) The fill

Filling a grid by hand is time-consuming but worthwhile, because you can be creative with using pop culture references, proper nouns, phrases, abbreviations, and whatever else the grid demands.

Since I was using a demo version of Compiler, I opted to try out its Autofill feature to see what my options were. As you can see, I ended up swapping the locations of SILVERSTONE and CHAMBERLAIN to improve my chances of a successful fill.

After settling on the fill for the center section (spreading from bottom left to top right), I started working on the fill for the top left portion.

Here’s the best fill the program could offer:

But I wasn’t satisfied with it, so I began tinkering on my own.

That’s probably the most daunting part of making your own crossword, but there are numerous resources available to the aspiring puzzle creator.

Not only are there Autofill programs like the one employed by Compiler, but there are also websites where you can input letter patterns and see what your options are. Both Onelook.com and Xwordinfo.com are terrific resources.

Here’s the result of my own tinkering:

There would be further gridwork throughout the editing process, as I eliminated abbreviations, vocabulary I gauged as too difficult, and grievous examples of crosswordese.

Don’t get discouraged! I had to try lots of different word combinations to make it come together. All of which was time well spent in my opinion.

Here’s my completed grid:

As you can see, including phrases and pop culture references definitely helped out, especially at middle left where JAWAS was a handy inclusion, as well as bottom center where IFI and AFOOL are crossing.

Which brings us to the grand finale.

4.) The cluing

Now, cluing takes on an entirely different dimension if you’re hoping to publish your crossword, versus the cluing style you’d use for a homemade puzzle for a friend or loved one. When it comes to published puzzles, your clues need to be interesting, engaging, and more than a little crafty.

(Note: It’s true that the theme is often what sells your puzzle to editors like Will Shortz, but a reputation for clever cluing is always a good bonus.) 

For instance, a puzzle of celebrity names could prove a bit boring when it comes to cluing, but I chose the entries I did intentionally, because I already knew the clues I wanted to write for them. (These clues were based on a series of outstanding puns a friend of mine made on Twitter.)

My theme is Celebrity Groupings, and the clues reflect that.

17 Across: A ____ of tuxedo belts
8 Down: A ____ of discarded Old English words
53 Across: A ____ of shriveled utensils

In this instance, the clues make all the difference.

Of course, if you’re making a crossword as a gift, the above still applies. Cluing makes all the difference. You can tailor the clues specifically to the intended recipient. Inside jokes and references should run rampant, even for the words used in the fill.

For 37 Across, you could say “What Uncle Rob does for at least three days longer than necessary.”
For 39 Down, you could clue it as “General Kittybuns’s sign of pleasure.”

Have fun with it! If you can make them laugh or say “Oh yeah!” and remember a fun moment while they’re solving, it makes the gift even more special.

And if you do try constructing your own, let us know how you did! We’d love to see what our fellow puzzlers and PuzzleNationers come up with!

[Stay tuned, aspiring constructors! On Thursday, I’ll be posting part 2 of today’s How To, featuring advice from published constructors and puzzlemakers!]

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