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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My Favorite Crosswords from 2017!

One of my New Year’s Resolutions last year was to solve more crosswords.

I wanted to sample as many outlets as possible, really immersing myself in the tricks and techniques that constructors use to create really topnotch puzzles. And I definitely solved more crosswords from more publishers than ever before.

And any time a puzzle really impressed me, or made me laugh out loud, or presented an enjoyable challenge that lingered in my mind after the solve, I put it aside in a little folder.

So now, I’d like to give those puzzles and their constructors a little love as I share my favorite crossword puzzles from 2017.


My collection started early in the year when David Steinberg celebrated the 125th anniversary of Stanford with a crossword that not only wished the university “happy birthday” in circled letters in the grid, but spelled out the number “125” when you connected the circles!

Peter Gordon marked 7/7/17 on the calendar with Fireball Newsflash Crosswords #7, and went all in on the 7s, placing three entries in the puzzle that were clued as “capital of a seven-letter country/state.”

Patrick Blindauer’s “End of the Summer” puzzle from the first edition of Piece of Cake Crosswords celebrated Labor Day with shaded entries that clued multiple down entries, depending on whether you filled the shaded space with LAB or DAY. So, for instance, you could have LAMP and BEAR or DAMP and YEAR reading down for their particular clues.

[Image courtesy of TV Tropes.]

For brazen acts of punnery, it’s hard to top Patrick Blindauer’s “For Fudd’s Sake” Piece of Cake Crosswords puzzle. Theme entries like WOOKIE MISTAKE definitely had me laughing. Then throw in clues like “Instrument that becomes a dessert if you change its first letter to a J” for CELLO and “What my fiancee said to me on September 16, 2011” for I DO, and you’ve got a great solve.

Then again, there was COOLIO JETS in Brendan Emmett Quigley’s “No Big Pun Intended” crossword from March 30th, MOSTLY ARMLESS from Patrick Blindauer’s “True ‘Liza” Piece of Cake Crosswords puzzle, and entries like PIGNORAMUS, LAMBITION, and SQUIDDITCH from Patti Varol and Dave Cuzzolina’s June 30th LA Times puzzle.

And how could you resist the wordplay in Quigley’s “Next Level Shit” puzzle from November 2nd? Entries like LAKE TITICACA and SKYSCRAPER AD were purposely broken up onto ascending rows, so that CACA and CRAP(ERAD) read out on the “next level.” It was shameless and very inventive all at the same time.

[Image courtesy of Scientix Blog.]

Nobody keeps it current like Peter Gordon with his Fireball Newsflash Crosswords, and #20 from March 3rd had a lot of fun with the snafu at the Oscars, first giving us “Winner of the Oscar for Best Picture at the recent Academy Awards” as a clue for LALALAND and then correcting itself later with “There’s been a mistake! Actual winner of the Oscar for Best Picture at the recent Academy Awards” for MIDNIGHT. Beautiful trolling there.

He did something similar in the “Themeless 107” Fireball Crosswords puzzle that had HARRY ANGSTROM as an entry, and then referenced it in another clue — “Film character whose last name is roughly 95 septillion times longer than 23-Across’s?” — for BUZZ LIGHTYEAR. The science/math nerd in me popped for that one.

I’m a sucker for ladder puzzles, so when Mary Lou Guizzo and Jeff Chen snuck one into their May 5th puzzle in The Chronicle of Higher EducationAPE, APT, OPT, OAT, MAT, MAN — and an evolutionary one at that, I very much enjoyed it. The cluing only added to the fun, with clues like “Member of a Latin lover’s trio?” for AMAT and “Kiddie or chick follower” for LIT.

The Chronicle of Higher Education struck gold again on April 21st with Ed Sessa’s puzzle “That Boxed-In Feeling.” Not only did the puzzle feature several confined spaces like MRI MACHINE and PHONE BOOTH as theme entries, but CLAUSTROPHOBIA was jammed into the center of the puzzle — two letters per square — to really bring the theme home. Really nice, tight gridwork there.

(For the trifecta, I also enjoyed George Barany and Michael Hanko’s July 21st puzzle in The Chronicle, “Side Order,” which used BERMUDA TRIANGLE, TIMES SQUARE, and THE PENTAGON to complete a themed GEOMETRIC SERIES.)

Another puzzle with a lot of interplay between cluing and theme answers was Jacob Stulberg’s “Two Descents’ Worth” Fireball Crosswords puzzle. This one had entries like DRESSING, STRIPPED, and UPSIDE, which were referenced in clues for CENSURE, BASIC, and FLIPPED.

You see, the theme here was DOUBLE DOWN, so a double DRESSING down would be CENSURE, something doubly STRIPPED down would be BASIC, and being doubly UPSIDE down would be FLIPPED. I confess, it took me a while to parse out the relationships between these entries, but once I did, I was very impressed with the imagination and constructing skills necessary to make the puzzle.

[Um, no, not THAT Double Down. Image courtesy of YouTube.]

There were also some grids that really played with word placement and omission in super-clever ways.

Tracy Bennett’s “To Everything There is a Season” puzzle from the Indie 500 tournament offered a grid with four-way symmetry built around the four seasons, which all appeared within the grid. Having the clues set at 90-degree angles to coincide with word placement in the grid was a nice touch.

Timothy Polin’s “A Prynne String,” the January 13th puzzle for The Chronicle of Higher Education, had four As in the grid that “concealed” the letters RED both across and down, so LEERED AT and HUNDRED ACRE WOOD became LEEAT and HUNDACREWOOD. It took me a while to figure out the game here, and when I did, I was really impressed with the grid construction and creativity.

[Image courtesy of The Odyssey Online.]

Ed Sessa makes his second appearance on the list with a March 24th Los Angeles Times puzzle that played nicely with a classic idiom — Leave no stone unturned — by hiding stones within the other theme entries. For instance, AGATE read out backwards in TILL WE MEET AGAIN. He let us in on this clever hook with the revealer NO ENOTS UNTURNED. Nicely done.

(Brendan Emmett Quigley did something similar with his “Halfbacks” puzzle from June 8th, with entries like HIGH GERARD, RADIO SIDNEY, and ALFRED PANTS, as did Erik Agard with the “Bottoms Up” puzzle from the Indie 500 Meta puzzle pack, sneaking drinks like OJ and DECAF into the down-reading entries JO WALTON and FACED THE TRUTH.)

Quigley took it a step further with his April 6th puzzle “Catch You on the Rebound,” as the themed entries required you to fill in the boxes one letter at a time, then place the rest of the letters backwards on the same line, forcing two letters to share squares. For instance, THE POINT OF NO RETURN spelled out THEPOI(NN)(TR)(OU)(FT)(NE)(OR), with RETURN reading backwards in the boxes.

Alex Eaton-Salners did a tough variation on this idea in Peter Gordon’s Fireball Crosswords with “Kicking Off the Fourth,” as his theme entries started backwards and then doubled back on themselves. For instance, POTATOPEELER was written as ATOPEELER, with the POT reading backwards, “kicking off the fourth” letter with the A, then reading forward with the rest of the entry. NRUBBER for BURNRUBBER, EDISHES for SIDEDISHES, and AVAVOOM for VAVAVAVOOM were just some of the NINE entries that fit the pattern. A top 5 puzzle of the year for me, easily.

[Image courtesy of Shutterstock.]

And I have to close out today’s post by mentioning Alex again for his “Read the Fine Print” Fireball Crosswords puzzle. This one actually used some of the numbers within the grid as part of the entries. Box 1 was filled with a 1 for 1 CUP and 1 PIN, Box 50 helped form 50 FIRST DATES and 50 CENT, and so on. I’ve never seen the actual cluing numbers incorporated into the answers like that before. Really terrific stuff.

There were so many great, creative, well-constructed puzzles that a post like this just scratches the surface. (Especially since I’m behind on my solving for The Crosswords Club and a few other outlets!)

I’m sure I missed plenty of worthy puzzles from constructors all over. Feel free to let me know your favorites in the comments section below! (And come back tomorrow to learn some of the favorites from others in the puzzle community!)

I’m continually amazed by the innovation, reinvention, and endless possibilities clever constructors can mine from these curious collections of white and black squares.

I can’t wait to see what they have in store for us in 2018.


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