Natan Last Documents the Past, Present and Future of Crosswords

We sat down with Natan Last, a prolific crossword constructor whose puzzles have appeared in major outlets like The New York Times and The New Yorker. Last, who has been constructing crosswords for over half his life, shares insights into his creative process, the evolving landscape of the crossword world, and snippets from his upcoming book, Across the Universe: The Past, Present, and Future of the Crossword Puzzle.

How did you first get into crosswords? What was your journey like 

I started as a high-school student as a solver. It started in AP U.S. History class. We’d have a free period afterward, and a few of us would sit together and solve The New York Times crossword. It was fun to see the collectivization of our knowledge. We couldn’t do it without sharing what we knew. I’ve also always been a doodler; I loved making mazes on graph paper in chemistry class. My dad’s a middle school math teacher, so graph paper was always around. So, boxy things came naturally.

The real spark ignited in high school when I was a tour guide at the Brooklyn Aquarium. You had to pick an animal to specialize in. All my friends picked the walrus, and I picked the seahorse. The seahorse class was like 20 minutes, not a lot of seahorse facts. So, I started doodling a rudimentary crossword and was hooked. It felt like drawing with words. Soon after, I downloaded Crossword Compiler and, as a sophomore, made a few rudimentary grids. I wrote a cover letter with my dad’s help and mailed them to Will Shortz. He accepted the second puzzle I ever sent and asked how old I was. To his credit, he was really interested in developing younger constructors. He encouraged me, complimented my clue writing, and suggested I go to the ACPT, which happened to move to Brooklyn where I’m from. Getting to meet all my heroes was great. I got hooked at that point.

When people solve your crosswords, what do you want them to feel?

I want them to feel pleasantly challenged. I want them to feel like the world is full of really different and interesting things. Especially for themeless puzzles, as I talk about in my book, they feel like mixtapes. I want a solver to feel the way I want a crush to feel when I send them a playlist of all my favorite songs, that these things cohere, they’re all interesting, but they’re all different. I want that sense that someone has curated an experience for them.

“I want [solvers] to feel pleasantly challenged. I want them to feel like the world is full of really different and interesting things.”

Q: Do you feel your personal voice or interests come through in your puzzles?

Definitely. I think I have a distinct voice. I’ve been writing puzzles for more than half my life, so my own tastes have changed. In high school, I was thrilled to put Simpsons characters in. Now, I think I have a clever clue writing style, but in terms of proper nouns, I’m very internationalist because of my work in immigration. I’m interested in words from different cultures and in singers, politicians, and novelists from different countries. That’s a big marker of my puzzles.

What advice do you have for new constructors?

It can be useful to mimic your masters at the beginning. I loved Elizabeth Gorski’s puzzles and Brendan Quigley’s themeless grids, and I tried to make puzzles that looked like theirs in grid shape and mimic their clue writing style – Brendan’s irreverent but clever style, and Frank Longo’s devilishly hard clues. Imitation is the highest form of flattery here; you learn a lot about the form by copying the masters.

“Imitation is the highest form of flattery here; you learn a lot about the form by copying the masters.”

Finding an actual mentor is also huge. The puzzle world is teeming with new and veteran constructors, so it’s easier than ever to find someone to shepherd you through the early process. This is probably more useful than ever because when I started, The New York Times was basically the only game in town. Now, my advice for young constructors is that figuring out where you want to send your stuff is just as important as what the stuff actually is. There’s a proliferation of outlets—blogs, Muse Labs for hosting your own puzzles. So, having a conversation with yourself and the crossword community about where your puzzles should go is a real help.

Is there enough stylistic diversity across different publications now when it comes to crosswords?

Absolutely, 100%. Now that I construct so many themeless puzzles for The New Yorker, I’ve had puzzles rejected by The New York Times where they explicitly say, “This feels more like a New Yorker puzzle. It’s more literary, maybe hipper in some ways.” Just like submitting to a poetry journal or news magazine, you want to read their stuff to get a sense of what they like. It’s the same with puzzles; you really want to solve a bunch to know the stable identity and voice of a given outlet.

How do your diverse interests, like poetry and policy advocacy, show up in your crosswords?

Cameron Austin Collins always says a good puzzle should feel like a full meal, with sides and mains and diverse cuisine. For me, a typical New Yorker puzzle might have a lot of poetic and literary references, but also references to heads of state in South Africa, or I’m more likely to put in DACA as a four-letter answer than some other constructors. That stuff inevitably creeps in because it’s part of who I am.

The part of my brain that loves crosswords is not entirely similar to the part that loves immigration advocacy, but there’s overlap in broad terms like problem-solving and a combination of rhetorical and mathematical thinking. They scratch similar itches, but what I’ve found is that working in advocacy for over 10 years has actually enabled puzzles to feel more like an art and stay in that art part of my world, the way poetry does. I don’t feel as much pressure for it to be more than that; it can feel like pure pleasure.

What are your thoughts on the place of politics within crosswords? Should puzzles be timeless or reflect current political inclinations?

It depends on how often the venue comes out. I loved Brendan Quigley’s early blog puzzles. I remember the day Sonia Sotomayor was confirmed to the Supreme Court, and the next morning, Brendan had a crossword with Sotomayor as an answer. He wasn’t just discussing current events; he was codifying it immediately in the crossword.

Every puzzle has its politics one way or another. I think there’s room for venues that are really responsive to current events and are upfront about that fact, just as there’s room for places that want to be timeless. Of course, puzzles will still include things like EDM for a long time, and hopefully, a brutal dictator isn’t as timeless as we’d want. I think using the puzzle as a spotlight for a constructor’s particular politics makes total sense because you’d get a different politics on a Monday from one constructor than on a Tuesday from another. I’m totally fine with that diversity of voice. It’s important to acknowledge that no puzzle truly avoids this question; it’s about looking at it head-on and honoring the constructor’s voice.

“Every puzzle has its politics one way or another. I think there’s room for venues that are really responsive to current events and are upfront about that fact, just as there’s room for places that want to be timeless.”

Can you give us a teaser from your upcoming book about the history of crosswords?

I’m still so fascinated by the crossword craze of the 1920s, peaking in 1924 and 1925. There are images of crossword-print dresses, women wearing crossword stockings, and songs like “Crossword Mama, You Puzzle Me.” The crossword truly took the world by storm because, after World War I and the transition to an industrial economy, Americans had leisure time for the first time ever. They started playing games and holding crazy competitions like flagpole sitting and Mahjong. That energy is really exciting.

Another thing people can look forward to is how more stoic or conservative voices reacted. The New York Times in 1925 published a piece called “A Familiar Form of Madness,” decrying the crossword and saying, “Last year it was Mahjong. This year it’s crosswords. What will the kids think of next?” In fact, The Times refused to add a puzzle until World War II, until Pearl Harbor. So, people can look forward to that battle and how The Times has changed throughout its history—from decrying the crossword as a children’s game to seeing it as useful in World War II as a balm for people on the home front, all the way up to now, where games are such a fundamental part of The Times’ business model that people in the news desk joke that The New York Times is a gaming company with adjuncts. That evolution is particularly fascinating.

In tracing the history of leisure, do you draw parallels to today’s “distraction economy”?

Definitely, I think about it a lot. The fourth chapter of my book is a big politics chapter, tracing the puzzle’s role from being seen as a “bad distraction” in the ’20s and ’30s to a “useful distraction,” all the way to COVID, when puzzles became this thing we could all do to distract ourselves from a world-historic tragedy.

Crosswords, in particular, want to have it both ways. They feel like intellectual labor—answering trivia, writing—but ultimately, it is a frivolous game. Crosswords embody this contradiction as a distraction. If you see someone solving a New York Times crossword on their phone, it doesn’t feel the same as them playing Angry Birds or scrolling Instagram. But, as I write, over the past five to ten years, The Times‘ games team has become such an important source of revenue, almost a tech startup within this big institution. So, there’s a dark side: the same behavioral science instincts that make Instagram addictive recur in designing these games; we want people to be engaged.

At the same time, I write about how the puzzle can take us out of everyday distraction and connect us to our past. The Times used to have something called “Solver Stories,” which were beautiful. For instance, a woman cleaning up her recently deceased father’s papers found partially solved Sunday crosswords and finished them, sometimes even correcting his answers. Rather than being distracted from his death, she was able to pay attention to the things he was good at, like his knowledge of mythology. So, there are ways in which the puzzle brings us together. It’s a deep subject, and it’s hard to talk about because I’d like to use my phone less and be less distracted. Crosswords are yet another thing I can distract myself with and convince myself it’s a good kind of distraction. In some ways, it is.

How has software influenced your construction process? Are you a purist, or do you use tools that make crossword construction easier?

I definitely started on graph paper and pencil. There’s a part of me that believes starting on paper taught me a lot about the statistical structure of English words and where consonants tend to be. Placing black squares, which isn’t an automatable process, is something you learn a lot by starting on paper or with software.

So, I’m not a purist, but there are moments where the software can make the job seem too easy, especially from a fill perspective. There’s almost a slow food movement among some constructors who grew up on software; they’ll turn the software off for a challenging corner and try to fill it themselves to truly feel like they’re choosing every word. I use Crossfire and Ingrid. I don’t use any AI for construction; I don’t think it would be very good for many processes. I admire people like software engineers or scientists who create themes that an AI could never come up with. If I want to find all words that remain words if I add an “A,” writing a little script is fun and useful for seeing the full sweep. So that works in a complementary way. I also enjoy puzzles that an AI could never have come up with or software never could have helped with. It’s definitely both; I’m not a purist, but I’m also not a futurist. I think we’re in a nice middle ground.

And that’s to say nothing of distribution tools like Muse Labs. When people could embed puzzles on their own blogs, that really changed the game. I love how technology has made distributing puzzles easier and more widespread. I use it as an ambivalent tool in my own process.

How has your experience been with PuzzleMe?

I like it; I think it looks really good. It’s a good service to have a single, standardized way to display these things. One of the things I like most about it is that it enables all these blogs, which is huge. Also, the balance you strike between customizability and standardization is hard to achieve, but you do it well. I think about Margaret Farrar, who joined The New York World and realized the puzzle was chaotic. She standardized things, which enabled a lot of innovation. It’s like a poetic constraint: once you have the rule, you can innovate on top of it. PuzzleMe is similar; this standard way to display puzzles has allowed people to do weirder things because they have this base. That’s really nice.

What are your thoughts on the evolution of PuzzleMe?

It’s cool that you guys are a born international, born global company. I get asked all the time if there are crosswords in other languages, and thanks to you, there can be many more, which is awesome.

When and where can people buy your book?

The book comes out in November. Pushing pre-orders really helps authors because they signal to bookstores that there’s a lot of excitement. 

Is there anything else you’d like to share that we haven’t covered?

One thing I’ll say about the structure of the book is that the crossword world brings together people with really disparate interests. If you’re a computer or math head, you can think of the puzzle as a computational linguistic form. If you’re an arts or literary person, the puzzle is a curatorial object, and people use it to bring attention to aspects of culture they like. And if you’re a political animal, there are the ways the puzzle itself has politics, and then there are the interesting stories, like Mangesh’s or the World War II stories, about how the puzzle has shaped other people’s politics and political lives. So, the book covers those three sections: technology, art, and politics. What I love about puzzles is how vibrantly the community takes up each of those different causes.