1133. This week, crossword pro Natan Last talks about his book "Across the Universe." We look at the technical and cultural differences between American and British puzzle styles and the secrets that will surprise you about how clues are written and edited. We also look at "crosswordese," the long submission process for the “New York Times,” and the AI that won a human crossword tournament.
1133. This week, crossword pro Natan Last talks about his book "Across the Universe." We look at the technical and cultural differences between American and British puzzle styles and the secrets that will surprise you about how clues are written and edited. We also look at "crosswordese," the long submission process for the “New York Times,” and the AI that won a human crossword tournament.
Find Natan Last at Natanlast.com.
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[Computer-generated transcript]
Mignon Fogarty: Grammar Girl here. I'm Mignon Fogarty, and today I am here with Natan Last, author of a fabulous new book about crossword puzzles called "Across the Universe." At 16, Natan was the youngest person ever at the time to get a Sunday puzzle accepted by the New York Times, and now he teaches crossword writing classes and regularly contributes puzzles to the New York Times and the New Yorker. Natan, welcome to the Grammar Girl Podcast.
Natan Last: Thank you so much for having me. It's a thrill to be on.
Mignon Fogarty: Oh, I'm excited to have you. I really loved your book. I think it's going to be, I'm going to get some as gifts this holiday, for people. I learned so much, so you're going to hear me say I was surprised so many times in this podcast. So one, I was surprised to learn that American and British puzzle conventions are different.
Natan Last: They're very different. Yeah. They kind of play to type a little bit. So the British style is pure cleverness. In look, they are lattice-shaped, so they look like waffles, and they don't have as many crossings. There are fewer crossing words. But each clue is kind of built up out of puns and riddles and sly bits of language, whereas the American style that we're all familiar with has that huge swatches of white space and more pop culture cleverness here and there, but a lot of trivia as well.
Mignon Fogarty: So like if I went to do a British crossword puzzle, would I find it, like, is it hard to cross the two styles or do people go back and forth pretty easily?
Natan Last: There are definitely bilinguals for sure. It really really scratches a different itch and uses a different part of the brain. The kinds of clues you would see in a Friday or Saturday New York Times crossword sometimes with a question mark indicating that wordplay is afoot. Every single British style cryptic crossword, they're called, is like that. And so if you like that style of the Friday and Saturday deviousness, then the British style is definitely for you.
Mignon Fogarty: And is one style older than the other?
Natan Last: Yeah, the American style crossword sort of is the one that comes first, and it's not really until after World War II, where for instance, the Times starts publishing a crossword that the divergence happens. But as early as the, you know, the 1920s and thirties, the two styles are pretty much, or the two countries, I should say, are pretty much doing the same thing. Crosswords, kind of like we know them today when we open up the New York Times.
Mignon Fogarty: Okay, so the other thing that surprised me is I was just stunned at how long it can take from when a crossword puzzle is accepted to run in the New York Times, between like when it actually shows up in the paper or on the website.
Natan Last: It can really be a long slog. Yeah. When I was younger I remember, you know, you get so excited when you get that coveted crossword subject line from Will Shortz and his team. And it can be a year, sometimes more until you see publication. One of the interesting things that happened is that a huge crop of blog puzzles and this indie scene where
people wanted to respond to the moment, right? Wanted to use crosswords more as a barometer of language to use it to kind of take the temperature of the culture and the words being spoken in that culture. And so I remember solving a Brenda Emmett Quigley, who's a great, great constructor, puzzle in 2009, the day after Sonya Sotomayor had been confirmed, and seeing her name in the grid kind of had a hand in confirming that this was indeed common knowledge, that this was a name we all should know that rather than waiting for some other codification right away, a constructor could lift something up into the realm of common knowledge.
Mignon Fogarty: Yeah, I love doing puzzles that have current events in them. Why does it take so long at the Times?
Natan Last: It's mostly just due to, you know, supply and demand. There are so many really good puzzles that they get, that's only increased as the Times Games app has expanded. It's got more eyes on it. The interest in construction has expanded. That's started to happen right when the Times went digital before COVID, and in COVID, a ton of people got really, really excited about trying their
hand finally at construction. These are long-time solvers who really love the game, and so there's just a lot of good puzzles. It takes a long time to read each submission individually and figure out where it should go, if it's Times worthy. And yeah, there's just an explosion of interest, and so there can only be so many puzzles a week.
Mignon Fogarty: Yeah. Yeah. And one reason I expect you to know this actually is that you interned with Will Shortz. So what was that like and how did he change the game?
Natan Last: That was a ton of fun. I was Will Shortz's intern when I was at the end of my high school and early college days, and I would just take the train up. I grew up in Midwood, in Brooklyn, so I'd take the Q to the 4, to the Metro North to his wonderful hamlet called Pleasantville, where he worked from home.
He was the first adult I met who worked from home, and he'd greet me in, you know, crossword print PJs at like 10:30. And I was like, this is the life. This is how you do it. And we'd go up to his study and there'd be a clipboard of that day's puzzles, and we'd just go through them clue by clue together.
Natan Last: Editing for difficulty, if this was a Wednesday puzzle, but it read more like a Tuesday, we'd beef up the difficulty by introducing some deviousness, some question mark clues, maybe some hard-to-unearth trivia, and we'd, you know, look stuff up together. So I'd, you know, Google while he took a big book off the shelf, and I'd always win that race, of course. It was really really nice. And I would also get experimented on, so he'd do the NPR weekly puzzle. He'd test that out on me before we went up to edit. And if it was, if I got him too quickly, he'd always make it harder.
I remember being the kind of patient zero on the really kooky and wonderful Sunday NPR puzzles that he runs.
Mignon Fogarty: That's amazing. So I was also surprised that, so you were doing more than fact-checking. You're like changing some of the clues on people's puzzles, right?
Natan Last: Yeah, for a long time it was sort of an insider's secret that Will Shortz and editors in general can change up to 90% of the clues which is a lot. Right? And so, I mean, for a long time it was kind of unnerving to wake up on publication day 'cause it was an era where you didn't get any proofs.
So you'd wake up and you'd see your clues massaged into an entirely new direction by a firm hand, but maybe not in a way that you necessarily agreed with. Sometimes that's just changing difficulty and tweaking the trivia that's asked for, tweaking a reference. Sometimes it's lighting on a really fun question mark or devious clue that can kind of spice up an existing puzzle.
Other times it's simple things like the New York Times clue syntax is a structure, and not everyone immediately knows how to imitate that structure. So it really can be anything, anything from making it harder to just conforming to Times style. And yeah, older salts who have been making puzzles for a while would only change maybe five, 10, 15% of their clues.
But often if someone had never made a puzzle before, the theme was really fun, the answers in the grid were totally interesting, but the clues in particular needed that kind of TLC.
Mignon Fogarty: Oh, that's fascinating. Okay, and so I want to go back to the crossword puzzle pajamas 'cause that's adorable. So like, is his whole house like crossword kitsch?
Natan Last: Totally. Yeah. Will Shortz is a real…his house is a museum. He’s a real connoisseur and collector. and one of my jobs when I was a high school student was to go into his extremely haunted basement and page through - he had hard copies of the 1925 New York Herald Tribune. In the mid-twenties, there was a crossword craze.
So the first ever crossword puzzle book comes out in 1924. And then, in an echo or pre-echo of those crossword print PJs, people are going to crossword balls and wearing black and white checkered dresses. There's this wonderful crossword dress with a peplum cube hat, and everyone has been bitten by the crossword bug. It's called crossworditis. The sort of generation above treats it like a disease, a madness, a craze, and so Will Shortz's house is really an homage to ephemera from that time. He has crossword bracelets that have little five by five grids on them. He has puzzles from that era and everything from, you know, the clock in his study is a crossword, and the minute and second hand are pencils, right? It's all crosswords.
Mignon Fogarty: That's amazing. So what, I mean, what were you going into the basement for though?
Natan Last: So I was combing through pages from the 1925 Herald Tribune to try to find any cultural residue from the crossword craze. And, you know, four pages in, I'd find an advertisement for crossword print shoes that had black and white buckles. I'd find, 20 pages later, an invitation to a crossword ball, in which you could see sort of dapper Dans with their pork pie hats.
And, again, these sort of 1920s flappers in black and white dresses. So I was looking for evidence like that, 'cause Will Shortz at the time was, I think, combining a lot of this into some kind of authoritative compendium. But it was mostly just an education in, you know, the Jazz Age, right? And what was going on in the newspaper world at that time.
Mignon Fogarty: How fun, and this is a complete aside, but I had no idea that he was also a huge table tennis player.
Natan Last: Will Shortz is really into table tennis. He purchased a table tennis club while I was his intern. I remember I was so young; I didn't really understand that you could amass that much in savings from, you know, Sudoku and crossword puzzle books and then essentially liquidate all of it so that you could play more games.
In this case, buy a table tennis club in Pleasantville. And he is, I think, essentially the Cal Ripken Jr. of table tennis, where he will sort of forego travel and events because his streak of playing table tennis every day cannot be interrupted. And yeah, he's a very talented player. I think of myself as someone who's pretty good at sports and loves table tennis, and he just whipped my butt every time. He's great at it.
Mignon Fogarty: That's amazing. It's like two so, so divergent, like things he's really good at. That's wild. I aspire to be that good at two completely different things.
Natan Last: Me too.
Mignon Fogarty: So the mathematical analysis of the games also just fascinates me. You talked in the book about, you know, the investigations into which words are like crosswordese.
Natan Last: Yeah, totally. So I think longtime solvers have all encountered crosswordese, which are those often vowel-heavy words that, because English is so consonant-heavy, thanks to its Germanic roots, you need that release valve of, you know, we all speak crossword French, right? Like, epe, and oui, all those vowel-heavy words that go underneath these consonant-heavy words that come from Germanic.
I think words like area and era are extreme crosswordese in the sense that they appear in crosswords so, so, so much, and we get kind of bored as solvers and as constructors having to clue them for the umpteenth time. But there are also words that are cross-wordy in this software engineer, no development took, words that appear a
ton in crosswords, but then don't appear in books. In this case, using the Google Books corpus. And those words are words like Ursa or Smee from Captain Smee from Peter Pan, where the only context in which you encounter that letter combination is in crosswords, right? So those are the crosswordiest words.
Mignon Fogarty: And there's like a numerical ranking that constructors can look at, right? And say how crosswordy is this word?
Natan Last: Yeah, exactly. The field has become extremely soaked in quantitative data for good and for ill, I think. But, you know, there's a great website called XWord Info, in which you can analyze a puzzle, right? You can see which words have never appeared in a crossword before. So they're exciting 'cause their debuts, as far as the New York Times is concerned, or you can see, you know, which words have high Scrabble value, right?
Which is to say if you tallied up the letters' rankings in Scrabble, because you've got a lot of Qs, Xs, and Zs in a word, you know, a word like jacuzzi scores really high in Scrabble value and is an interesting word, but also getting those Js and Zs into a puzzle can often lead to interesting words going down as well. So there's tons and tons of data for the curious, for sure.
Mignon Fogarty: Yeah, so do people who write cross— I keep wanting to call them writers, but are they constructors or what is the right word for people who make crossword puzzles?
Natan Last: Yeah, constructor, I think, is the sort of modal term, but I think that one of the things I talk about in the book is that I really think that different words that people use have a different crosswording ethic underneath them. So I think, I mean, people who love to do the clueing, right? Writing clues is like writing. And so I think a lot of people who are on the literary side and maybe favor the clue part of the process call themselves writers. Building a grid is extremely mathy. The writer George Burek, you know, referred to the arithmetic of letters, right? And found that part very frustrating. Where all that matters is that words are a certain length and that they're, you know, they're digraphs.
So one letter next to another fits nicely, and that part I think lends itself to engineering and math types, and people who favor that aspect tend to call themselves constructors. People call themselves creators. You know, writing a good theme is kind of like planning a really fun scavenger hunt that only takes 30 minutes, and that feels like creation. That feels like a creative act that feels different from writing clues and filling a grid. And so there's all these words, but I would say constructor is the one that people use the most. And then if you are ever feeling kind of playfully snooty, there's cruciverbalist, which I almost never say out loud 'cause it takes too long to say. It's hard to, you know, I think I write in the book that that's the kind of word that you can kind of feel its glasses falling down on its nose as you say it. And so it's a wonderful word. But constructor is the term of art, I think.
Mignon Fogarty: So do one group of these people or the other get more excited about using a word that has never appeared before? And actually, if you use a word that has never appeared before in the New York Times, for example, does it make it more likely that your puzzle will be accepted since it's so competitive?
Natan Last: Yeah, that's a great question. People definitely strive to debut a word that is kind of more for crossword bragging rights than anything else. I don't believe—at least it wasn't the case when I was editing with Will—that you would look at a word and say, "Has this ever run in the Times before?" And if it hadn't, bump it up. People tend to look at a crossword grid, and Will would do this too. You'd put check marks next to words you thought were interesting. A word like jacuzzi would maybe get a check mark. If you didn't know a cultural reference, Will might put like a question mark or even a negative sign next to it, right?
You're almost like quantitatively assessing these words, but you're still using gut judgment. You're not going to the database. It's definitely the case that when people submit a puzzle, they like to dot it with words that have never appeared in a puzzle before. And I think the editors can sense when a puzzle is fresh. A puzzle has words that are new, either because they're newly in the language. One of the lovely things about puzzles is they do kind of hold this somewhat delayed mirror up to our own language. or because they're, you know, new proper nouns, right? Whenever a new Star Wars character with a weirdly spelled name comes out, everyone rushes to put it in their crossword, right?
Mignon Fogarty: Awesome. Well, you talked about the databases, and I do want to talk about how computers have changed crossword construction. But first, let's talk about how crosswords were made before computers.
Natan Last: Yeah, it was a lot of blood, sweat, and tears. You know, my dad is a public school math teacher, and so scratch paper in my house was graph paper. I would just use graph paper and Google, for the most part. Earlier than my time, people would use this thing called a crossword puzzle answer book, which is this enormous over a thousand-page book, and it looks like a dictionary, but the headings aren't like A to B, B to C.
Instead, the headings are blank, N blank D. And so it's all words that fit that pattern, right? There are seven or so letters or whatever. There's an N in the fifth position, and then D in the seventh, and then the next page would be blank N blank D or whatever. So just to find letters that fit a certain string required this big book in combination with a big brain, right? With just thinking about it. For a long time, it was a lot of graph paper, pencil, and lots of erasure.
Mignon Fogarty: You know what? I checked on eBay, and you can get the crossword answer book for just $7. With free shipping, now it's like 1200-plus pages.
Natan Last: That’s amazing
Mignon Fogarty: It is amazing, and there are a lot of them. I think because now everyone's using computers. So let's talk about when people started using computers to make crossword puzzles and how long it took before they could sell puzzles. I'm sure it was really bad at first, but how did it end up?
Natan Last: Yeah, the first chapter of the book profiles Eric Albert, who was the first person to really use software to try and create the grids to build puzzles. Eric really wanted to be a full-time crossword constructor. He was a software engineer for a long time and was getting a little bit antsy to try something new and he was like, maybe I’ll be a crossword constructor, and everyone was like, "It'll never work. It takes too long to make them. It doesn't pay that much, and you're better off just doing some other programming job." He said, "I wonder if a computer can help," and built a rudimentary program that helps fill a crossword grid. The key innovation is that it uses a ranking system.
Eric ended up spending something like three years going through every single word he had in this big, big dictionary file—right?—750,000 or so words and saying, "Is this a good word or not?" ranking it on a scale from, you know, yucky to fabulous. The main thing the crossword software did is privilege the fabulous over the yucky, which is to, filling the grid is tricky enough on its own, but not super complicated. What's hard is filling a grid well, filling it with words that are interesting because Eric likes them. A fun thing happens in this era where people start using this item called a word list, where they have a long dictionary file that comes with a bunch of rankings. Abbreviations are smaller numbers; fun phrases, like free jazz or whatever that have J's and Z's and are phrases are fresh, have higher numbers. Then people spend a lot of their time manicuring and tweaking that list, putting in stuff that only they would put in a crossword and taking out stuff that they happen to think is not particularly interesting and wouldn't be a word or a phrase that they would enjoy seeing in their own puzzle.
Mignon Fogarty: Yeah, so I imagine you wouldn't want, I mean, in the very beginning, there were probably prepositions like "of," or articles like "an." You don't want those in a puzzle.
Natan Last: Yeah, those are really boring, and crosswords have all these conventions. There are only words of three or more letters. Exactly as you're saying, it's because it's impossible to find an interesting clue for the word "of," right? These function words are just not that exciting on their own.
You're going to demote words like that. You're going to take things out that feel obscure. You're going to take abbreviations out. People feel differently about, you know, scientific terms, words that aren't in English, and everyone is going to, in this weird way, the software ends up letting folks express their own taste a little bit better, right? Because they're making these thousands of aesthetic micro-decisions about the goodness of words.
Mignon Fogarty: Yeah, and so did Eric Albert - he did end up selling puzzles, right?
Natan Last: Yeah, he starts this journey in 1989, and in the early nineties, he's a full-time crossword constructor for some years.
MIgnon Fogarty: He did it.
Natan Last: Yeah, he did it. He submits his first grids, and they get accepted by The Times, and what's really interesting is that Will Shortz has no idea that the grids and the answers in them are good and clean, right? As a constructor might say, there's not a lot of obscurities; there are not too many abbreviations. At that time, no one could tell that these were, you know, in large part, computer-generated.
Mignon Fogarty: Did he feel tricked when he found out?
Natan Last: I think that he was okay with it because the thing about crosswords is that that kind of arithmetical part of putting the words in the grid has always been susceptible to automation and has always had computer assistance in the offering. But the clues were all written by Eric. The themes were all brainstormed and devised by Eric, and so there's still all of this human ingenuity shining through.
Mignon Fogarty: Yeah, great. And then later, a guy named Ginsburg, I love, came up with a program he called Dr. Fill, FILL, which I imagine is like filling in the grid. His whole thing, it seemed like a, it was a journey.
Natan Last: Yeah, it is really funny. Dr. Ginsburg, Dr. Matt Ginsburg, is, you know, he's this storied artificial intelligence researcher. He has a doctorate from Oxford in math at the age of 24, I think, and starts a bunch of AI companies and starts building crosswords, he becomes a constructor, and then goes to the first crossword tournament where people solve as quickly as possible. It's a speed-solving tournament. People are so fast that he gets mad. He's kind of out for revenge, and he wonders if he can build an AI that solves puzzles. So, you know, we've talked about computer assistance in building a puzzle, but here he's like, "I wonder if I can do this."
And then there the community has its eyebrows raised for sure because it's one thing to interlock words with other words, which feels computational kind of from the outset, but writing good puns, coming up with clever misdirections, brainstorming a theme—they feel very human. In fact, at the very first tournament that Dr. Fill competes in, Will Shortz, who's the organizer of the big tournament, has 150 buttons made that say, "I beat Dr. Fill," right? Very much team human at the moment. Dr. Fill actually underperforms that year, and Will Shortz gets it exactly right. I think he handed out 143 buttons or something like that.
All throughout this time, Matt Ginsburg is wondering how he can make this software better. If you fast forward 10 years to the pandemic, he ends up teaming up with a Berkeley Natural Language Processing and AI shop—a bunch of researchers who in their spare time had gotten into puzzles and were trying to recreate Dr. Fill. They ended up marrying what we think of as kind of modern machine learning techniques, basically just screening through tons and tons of data with the kind of hardcoded knowledge about crosswords that Dr. Fill had in its silicon brain. It knows about anagrams, right? So if you have a pun like "the Satanic serves," which is a pun on the rushing novel "The Satanic Verses," but now it sounds like it's about really devilish tennis serves, it doesn't know that that's a phrase because no one's ever said that phrase before, but it understands that it's composed of a bunch of words, and it understands that if you rearrange the letters in one of those words, the whole new phrase is something it's seen before.
So it kind of does know a little bit about a typical crossword theme. And that tournament in 2021, I believe, where Dr. Fill wins it, you know, it beats everyone else, but it's not sort of allowed to compete in the tournament because the tournament is for humans, right? It ends up, yeah, it's the first, it ends up winning.
Mignon Fogarty: It beat everyone.
Natan Last: It beat everyone. Yeah.
Mignon Fogarty: I missed that part.
Natan Last: Yeah.
Mignon Fogarty: And so people were probably pretty annoyed.
Natan Last: People were annoyed. I think that Matt Ginsburg did the right thing. You know, I interviewed him. He said he talked to all the other game-solving AI people. So the person who made the AI that beat the first time this happened is in backgammon in the late seventies. And you know, of course, ever since then, AI game solvers have plowed through chess, they've plowed through Go, they've plowed through Texas Hold'em. And there is a sense with language that we're very protective. I mean, this should be our thing. We're humans, we're funny, we're creative, you know, we're infinitely productive when it comes to words.
And all of the other game-solving AI creators were like, you should hang up your cleats. You know, if you win twice in a row, people really start to think you're rubbing it in their faces. If you win and then lose, everyone calls the first time a fluke. You should quit while you're ahead. And so he does. And since then we haven't heard much of crossword-solving AIs. But it is kind of fun that after a decade of not winning, and after a decade of, in particular, human crossword makers deliberately trying to trip up the machine and succeeding, Dr. Fill ends up winning in that 2021 tournament and then calls it a day.
Mignon Fogarty: He's hanging up his chips.
Natan Last: Yeah, exactly. Yeah.
Mignon Fogarty: And there is this really human side to solving crossword puzzles. I loved the story of the woman who found her father's unfinished puzzles after he died.
Natan Last: Yeah, there's a really wonderful series in the Times called Solver Stories, and there's one about this therapist, Deborah Sosen, who after her father dies, finds this portfolio of unfinished Sunday puzzles that were all TimesSundays, and she commits to finishing them. And so she is seeing a kind of ghostly version of her now past father, you know, things he would know, like classics. All of those answers are filled in—things he thought he knew but never really did, like car makes. You know, he's got wrong answers in, and you have that weird moment of, you know, in pen going over her father's incorrect answers and kind of correcting them after the fact.
And then it's this fun collaboration across time because he was the person who taught her about crosswords. He schooled her in crossword ease, right? He had a queen's accent, so he would say like crossword ease, you know, things like eppe and eek and et—these the e-words that appear in puzzles so often. And it's this really lovely moment that, you know, talks about puzzles as something that we don't just do together in the present, but that is an intergenerational form of transmission. You know, the knowledge that is passed along, the stuff that our parents know that they teach us. Yeah, all of that is kind of held aloft in her ritual.
Mignon Fogarty: Yeah. You know, the thing with unfinished puzzles. I have so many unfinished puzzles, I can almost never get every word. How do people who make puzzles feel about it? If you're just going to Google and look things up to complete the puzzle, is that cheating or is that like, I'm going and learning things?
Natan Last: Yeah, I definitely think it's the latter. I think that it's your puzzle, you know, do with it what you will. You know, I think that I write puzzles now on a monthly cadence for the New Yorker, and those puzzles are hard. They're very referential and elusive. They talk about, you know, poets that I like, new literature, and not everyone's going to know the answers, but the hope is that the puzzle ends up being a kind of mixed tape or recommendation engine or after the fact you didn't know a thing, but you look it up and you think I might get this book. This sounds like an interesting person. So I think it's definitely up to you what you do with the puzzle.
And I also think a lovely thing about crosswords is that it's a language unto itself. And so I've seen people just get so much better at solving in a short span of time because they end up sort of cracking the code, right.
Mignon Fogarty: Yeah, and there's that code, the crossword is, and learning what all those words are and everything. Well, I just loved the book, Natan Last, it's called “Across the Universe.” If you're a Grammarpaloozian, we're going to talk in the bonus section about the early history of crosswords. Ben Zimmer told us some about it earlier this year, but Natan has like so much more in his book, It’s just fun and fascinating. So we're going to talk about that in the bonus section. But, Natan, thank you so much for being here. Besides “Across the Universe,” where can people find you online?
Natan Last: Yeah. This has been lovely. You can find me on my website, natanlast.com, and all of the social places, X, Instagram, and so on. I'm natanlast.
Mignon Fogarty: Perfect. Thank you so much.
Natan Last: Thank you.