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A.J. Jacobs on Jews, puzzles and how Sondheim changed American crosswords forever

The ‘Puzzler’ author shares his Wordle insights – and his puzzle collection.

Those who follow A.J. Jacobs’ masochistic career – in which he lived by the strictures of the Hebrew Bible for 365 days and thanked the countless people involved in producing his daily cup of coffee – may have had no problem solving a Saturday New York Times crossword a few years ago; Jacobs was the answer to 1-Down.“I thought this was the highlight of my life,” Jacobs said over Zoom from his home in Manhattan. “As a word nerd, this was the Holy Grail. My wedding was good, but this – this is what I had been waiting for.”

But for the many who aren’t devotees of Jacobs’ brand of endurance journalism, the answer was a head-scratcher. As the author’s brother-in-law was first to note, a cameo in a Saturday puzzle – the hardest puzzle of the week – was a confirmation of Jacobs’ obscurity. Crestfallen, but undeterred, this sent Jacobs on a puzzling journey, one that saw him answering The Times crossword religiously until one day – thanks to the intervention of a sympathetic crossword constructor – Jacobs was the answer for a Tuesday puzzle. High on that notoriety, Jacobs endeavored to write a whole book about puzzles.

In “The Puzzler,” Jacobs meets the man who put him in the world’s most storied gridded box. He goes to CIA headquarters in Langley to try and crack a famous cipher statue on its campus. Our hero gets lost in a corn maze in Vermont, plays a chess puzzle with Garry Kasparov and even represents his country in the World Jigsaw Puzzle championship (he and his family come in second to last). 

Jacobs views his new book, which includes notable puzzles from history and its own, brain-breaking puzzle contest with a prize of $10,000 (more info here) as an extension of his books “The Year of Living Biblically” and “Thanks A Thousand,” where he seeks to solve the riddles of his heritage and how to be grateful in an alienated world. 

I spoke with Jacobs, who is appearing in conversation with Times crossword editor Will Shortz at the 92nd Street Y April 25, about “Paddington 2,” Darren Aronofsky’s psychosis-inducing furniture and why Jews are such a puzzling people. The following conversation – which contains discussion of Wordle strategy and biblical groin handling – has been edited for length and clarity.

PJ Grisar: This is more than just a book – it’s a puzzle too.

A.J. Jacobs: I wanted to do a contest for the book because one of my favorite books when I was a kid had a hidden contest in it. So there is a secret code hidden in the introduction to the book. You don’t have to buy the book to get it because it’s available for free on the internet. You put that code into the website on May 3. It’ll open up to this crazy month-long puzzle adventure. I didn’t design it. I couldn’t win this contest. I would be shut out. In the end, the person who solves them all in the final round wins 10,000 actual dollars.

The book from your childhood was called “Charade” or something, right?


“Masquerade!” That’s it. I’m thinking of Audrey Hepburn. But I was actually thinking of “Paddington 2” because there is a plot in that with a puzzle in a book, and treasure somewhere in London.

The Greatest Movie Ever according to Rotten Tomatoes.

Better than “Citizen Kane!” That brings me to a good place to start: your origin story with puzzles. We find out that it’s sort of been the family love language.

The sixth love language is puzzles! I come by it honestly. My parents were huge puzzle fans. My dad was in the army in Korea and he would mail back crossword puzzles to my mom in the United States and they would each fill in a clue and mail it back to the other. That’s probably the least efficient crossword solving experience in history, but it was romantic. As a kid, I loved Games Magazine. I would draw mazes the size of my living room floor. I think that it did inform the way I look at the world because I do look at the world as a big puzzle and you could sort of see my other books as metaphorical puzzles. It sort of has framed my life.

They’re a huge part of everyone’s life now.

Weirdly, I started this project a couple of months before COVID. But the timing was eerie, because the pandemic was a boom time for puzzles like we haven’t seen since the Great Depression. Puzzles were harder to find than toilet paper and hand sanitizer. And then there’s the Wordle craze, which happened actually right after I finished the book. I had literally finished all edits on the book two weeks before it had closed and then I begged my editor saying, “We gotta just reopen it and put Wordle in somehow.” I did insert it in the introduction, literally the word “Wordle” is in the book. So it says, “At night I do that Times crossword and Wordle.” So that’s my Wordle coverage. 

I was going to ask you about any Wordle gameplay strategies or insights since we don’t have a full chapter.

Well, I am a fan. I’m not a rabid fan. The Spelling Bee, for some reason, is much more addictive to me. But I do play Wordle every day and I’ve read about the best strategies and there’s one engineer who designed an AI to do it. And he discovered the best opening word is “soare” S-O-A-R-E, which is a young hawk. And I do that, I put it in, I don’t feel good about it, though. I got it from an A.I. And yet, it does seem to be effective. So I use that, but I do actually appreciate people who do a new word every day. I feel that even though it’s riskier, it feels more sporting.

A podcaster I know starts with “roast.”

Michael Ian Black did a YouTube video where he puts in ‘robot’ as the first word everyday. His theory is someday that’s gonna be the word, but then he just does it for all six guesses. He’s just like, ‘well, maybe it’ll change.’ Which is an interesting strategy.

There might be some A.I. applications for Wordle. When I was doing a piece on it, I found out about Mastermind, which was developed by an Israeli postmaster. Of course, we had to do the secret Jewish history of Wordle.

Josh Wardle is not Jewish himself. I made a little list if you ever want to get to it about Jewish puzzle makers. I do think there are some great ones.

Well just in the book you encountered so many people. This is not the point of it, but, you’re looking at Darren Aronofsky’s puzzle desk for example.

Well Darren Aronofsky is an interesting case. He loves puzzles, as you can tell from his movies – there are all twists and turns. And so he commissioned this guy Kagen Sound, who is known to be the greatest wooden box puzzle maker in the world to make a puzzle desk. And it’s got 22 incredibly tricky puzzles and it takes hours to open a drawer because you have to solve this puzzle where you have to move a bunch of pieces around. The guy who made it spent four years on it. It literally almost drove him insane. He said he gave up all his hobbies and didn’t see friends for four years. It was like an Aronofsky movie.

It was like “Pi” or something.

Yes, it was like “Pi.” If you have the Venn diagram of Judaism and puzzles, there are so many overlaps. And I think because for several reasons: One, Judaism is a lot about curiosity and asking questions, which are at the heart of puzzles. To me, the most Jewish sentence form is an interrogative, a question. I was just at the Seder where we had the four questions. And Jerry Seinfeld – Jewish humor is a lot about “What is the deal with X?” And you know, the Talmudic tradition is wrestling, asking questions, wrestling with God, all that. 

When I was doing “A Year of Living Biblically,” I was trying to wrestle with some of these biblical passages. And there’s a passage in Leviticus that says, “If two men are in a fight, and the wife of one of those men grabs the private parts of the other man, then you shall cut off her hand.”

I asked a rabbi in Israel. “What’s going on here? This seems like a very specific and strange rule.” And he said, “Well, you’re looking at it on the surface – that is a very superficial reading. What it’s really saying is, ‘Do not embarrass your neighbor.’” And I said, “Okay, I can understand that. But why wouldn’t the Bible just say that? Why not just say, “Don’t embarrass another person,” instead of this whole story about grabbing private parts?’” And he said, “Well, the Bible and life are like a jigsaw puzzle; the fun and the challenge and the meaning comes in trying to solve them. And if a jigsaw puzzle came all assembled, then you’d return it.”

I thought it was a very interesting perspective. I’m not sure I 100% agree. But I do still think that it is a strange commandment, but I do like — you know, I, that’s a big theme in the book is “How is life like a puzzle?” And this was his rabbinic version of that.

There’s an awful lot of groin-grabbing in the Bible. Usually I think it says they grab the thigh or something, but I’m reading the Robert Alter translation right now. It will have a footnote that says “in the Iron Age Near East, grabbing another man’s” – that was how you made oaths.

Well, I had read – and I don’t know how true it is – that the word “testimony” comes from, how when you would testimony, you would have grab the other guy’s private parts – that is how you swore.

Sure, you’re vulnerable then! We enter into this book with a premise that’s Tikkun Olam-y kind of, that approaching the world like a puzzle could ultimately make the world a better place. Did writing the book confirm that premise?

I had not thought of Tikkun Olam, which I think means “to heal the world.” I guess this version would be more like, the world is in pieces. Let’s try to solve it. I don’t know what the Hebrew equivalent of that is. I love the idea of seeing the world as a puzzle and trying to solve it because I think it’s solution-oriented. I like that. It’s optimistic. There is a solution. Maybe there is maybe there isn’t, but if you don’t try, you’re never gonna find out. And I also think it’s just useful in practice.

If I am in a situation where I’m talking to someone from the other side of the political spectrum, there are a lot of lenses I could use. I could view that through the lens of a war of words: I am going to beat him down or or he’s gonna beat me down, which, to me, is not that productive because you’re not going to change either of our minds. But what if you viewed that discussion as a puzzle and tried to figure out what we really disagree about? Why do we believe what we believe? What can we do to change our belief? Is there something she could present to me or I could present to her that would alter our view? That’s much more likely to result in a productive conversation. Plus, it’s a lot more fun.

Watch the video below to see Jacobs’ puzzle collection, hear Jewish riddles and learn how Stephen Sondheim changed the world of crosswords.

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