How Word Puzzles Tickle the Brain and Satisfy the Soul

Many things keep me awake at night. I worry about my kids’ future. I worry about rising sea levels and declining democracies. But if I’m being honest, those worries aren’t the main cause of my insomnia. No, what robs me of the most sleep is an innocent-looking little grid of seven letters that pops up on my iPhone every day. I speak of the delightful and infuriating New York Times Spelling Bee.

To be precise, it doesn’t pop up every day. That’s the problem. For some reason, the genial sadists at the New York Times puzzle section have scheduled the find-a-word game to appear every night at 3 a.m. Which means that when my body wakes me up around 4 a.m. for a bathroom break, against my better judgment, against many promises I’ve made to myself, I grab my iPhone and click on the Spelling Bee, unable to fall back to sleep until I find the hidden word that uses all seven letters.

Ah, thank God. It’s “Pickled.” Or “Janitor.” Or “Petunia.”

Only then can I close my eyes with a mixture of relief and self-loathing.

So puzzles rule my daily schedule. The crossword at 10:01 pm, the Spelling Bee in the wee hours. I’m not alone. I’ve met many other puzzlers who confess through gritted teeth that they are middle-of- the-night Spelling Bee players. One Connecticut woman wakes up, solves the Spelling Bee, and tweets about it, all before 4 am.

The Spelling Bee fanatics have a name—the Hivemind. And in addition to complaining about waking up early, their other favorite pastime is griping about which words are omitted from the list of approved words. You type in a word full of optimism, press Enter, and the computer snaps back “Not in word list.” How can you not include ‘laird’!!! The Scottish landowner! More on the joy of complaining shortly.

The Spelling Bee was created by Times puzzle editor Will Shortz in 2016. It was meant to be a simpler alternative to other word games. As he explained to Times reporter Deb Amlen: “I felt that The Times already had the ‘tough word puzzles’ audience covered with its crossword, acrostic, and cryptic. The readers we weren’t reaching yet were ones who’d like something easier and more accessible.”

He was inspired by a game called “Polygon” in the Times of London. But Will made two key changes: He allowed solvers to reuse letters in the same word, and he gave it the cutesy name Spelling Bee.

Here’s an example: Solvers must find words with a minimum of four letters that include the center letter. (For the above puzzle, “theme” is legal, but “gem” and “math” are not).

And my Lord, did it take off. The New York Times doesn’t release statistics about its puzzles, but one source told me that it’s more popular online than the venerable crossword puzzle.

I don’t want to throw around the word “addiction” too cavalierly. But if addiction consists of an inability to stop doing something that is harmful to my life, the Spelling Bee has qualified ever since my son Zane introduced me to it several years ago.

When I wake up for good at 8 am, my first task is to find enough words to reach the highest level. Article deadlines? Helping my son find a Spanish textbook? A return call to the dermatologist about the weird mole? Those can wait until I hit the top level, “Genius.”

Why do I find it so infatuating? Maybe it’s the constant dopamine hits, one for every word discovered, another when the computer gives me encouraging feedback like “Awesome!”

If I’m feeling generous toward myself, I’ll say that I’m drawn to the Spelling Bee because it’s a metaphor for constrained creativity. Here are a mere seven letters—but from them spring dozens of words. They are like Lego bricks ready to be rearranged into a boat or a tower. Or maybe they are like ingredients (butter, sugar, flour, and eggs) from which come waffles, pancakes, and a hundred other tasty carbs. Constraints lead to creativity. As Orson Welles said, “The enemy of art is the absence of limitations.”

And then, of course, there’s the paradoxical pleasure of getting furious about what words Spelling Bee accepts and those it rejects. The official rule of the Spelling Bee is that it accepts “common English words.” But what is a common English word? Ah, that’s more art than science. And the man behind that controversial call is a clean-cut twenty-five-year-old puzzle editor named Sam Ezersky. He’s got one of the most powerful jobs in all of puzzledom.

I call up Sam, who says he loves his work, even though many mornings he awakens to tweets that troll him about the scandalous oversight of the day. There’s even a Twitter account dedicated solely to this purpose called “Not a Spelling Bee Word.”

I ask Sam how he chooses which words are allowed and which don’t count.

Like so much in the puzzle world, those decisions require a human touch, he says. It’s not something an algorithm can do. Sam tells me he doesn’t rely on any single dictionary. He uses a combination of sources—dictionary.com, Google, Merriam-Webster, Random House. As Sam explained in The New York Times, “one person’s expansive vocabulary or specialized knowledge is another’s obscurity or esoterica.”

But the line between expansiveness and esoterica is debatable.

Consider this controversial puzzle: Sam’s list of approved words included “rift,” “fiat,” and “train”—but not “raffia.” 

Raffia is a shiny, crinkly fiber from a palm tree. It’s what Easter baskets are often made of. I’d never heard of it, and neither had Sam.

“I certainly learned something new that day,” he says.

Raffiagate, as it is called by Spelling Bee fans, triggered a barrage of angry tweets and emails. One reader was so irate that he protested by sending a seventy-eight-yard spool of raffia to Will Shortz’s house, Godfather-style. Sam got the message. Since then, he has included “raffia” in the approved word list of several puzzles. Activism works!

The Spelling Bee gets critiqued from both sides of the political spectrum. Sam gets flak for being too woke—he doesn’t include any words that can be used as ethnic slurs, even if that word has an alternate meaning. And he gets flak for not being woke enough. Why “wingman” but not “wingwoman?”

And then there was the September 2020 puzzle that caused an epistemic crisis, at least for me.

I typed in the common verb “cope,” and the Spelling Bee told me there was no such word. I typed it in again, rejected again.

Wait—Was I having a stroke? Was I in one of those psychology experiments where the researchers insist the sky is pink just to see if you have the backbone to stand up and say, no it’s not?

I wasn’t having a stroke. Sam somehow had accidentally deleted “cope” from the list of approved words.

“What a shitstorm to wake up to,” Sam says, laughing. “That’s just a big mea culpa on my end…It was the perfect 2020 word, too. The jokes just wrote themselves.”

A typical tweet was “I can’t cope with the fact that cope isn’t on the list!”

The “cope” scandal was one of many occasions that have caused me to consider just how strange the English language is. Why do those four letters C-O-P-E mean something, whereas the same letters in a different order P-O-C-E signify nothing?

I tell Sam that one reason I like the Spelling Bee is that it makes me realize just how arbitrary the English language is.

“Oh, my goodness! I think about that all the time,” says Sam.

It’s not just that some letter arrangements are meaningless, while others bring up images and feelings. It’s also that English is highly irregular. Verb tenses, plural nouns, spelling—the language is totally unreliable and unpredictable, like a meth addict or a Real Housewife.

“Today, there was the word narrator in the Spelling Bee,” Sam points out. “Why does that end in or instead of er like other nouns from verbs? And why is it rater instead of rator?” Then there is the classic genre of negative words that have no positive equivalent: You can say “inept” but not “ept.” Sam says, “Just yesterday, I was thinking, why is ‘legalized’ a common word, but not ‘illegalized?’”

English “makes no sense at all. Consider merely the letter string ‘-ough.’ I might not be the first to tell you it has ten pronunciations,” writes Mike Selinker in the book Puzzlecraft:

tough (“tuff”), cough (“cawf”), bough (“bow”), though (“tho”), thought (“thawt”), through (“threw”), hiccough (“hiccup”), hough (“hock”), lough (“lakh”—that is, when it’s not pronounced “lock”), and borough (“burrah”— that is, when it’s not pronounced “burrow”).

English, in short, is a total mess. This has a lot to do with its sloppy origins—a mishmash of Latin, Anglo-Saxon, and words snatched from dozens of other languages.

I have mixed feelings about the chaos that is my mother tongue. On the one hand, it’s terrible for those trying to learn English as a second language. Or as a first language. Think of all the time we English-speakers have wasted memorizing weird spellings and irregular verbs. Consider the thousands of miscommunications and unnecessary arguments caused by similar-sounding words and words with ambiguous meanings.

On the other hand, the insanity of the English language is precisely the quality that makes it great for word puzzles, as well as a playground for novelists and poets who like to fiddle with language. Imagine a crossword puzzle in Esperanto, with its sensible spelling and regular verbs. It’d be eye-glazingly dull.

English’s abundance of strange words makes the Spelling Bee interesting—and also makes finding every single word in the grid a monumental task. In fact, the final level of the Spelling Bee is not even advertised to solvers. My son Zane recently told me that the “Genius” level was not the Spelling Bee’s top score. You achieve “Genius” when you get about 70 percent of the total possible words.

If you get every single one of the possible words, a rare feat, you are rewarded with an Easter egg: the “Queen Bee” title.

It took me several weeks and hundreds of random guesses of four-letter combinations, but one Saturday morning, after two hours of work, I finally got Queen Bee. And then vowed to never attempt it again.

I still wake up at 4 am most days to check out the Spelling Bee—but I resist the temptation to try for Queen Bee. I consider this resolve a great victory.

Anagrams, The Ars Magna

The New York Times Spelling Bee is less than a decade old, but it’s based on one of the most ancient genres of wordplay: anagrams, the rearrangement of letters in a word to form a new word.

Humans have been obsessed with anagrams practically since the birth of the alphabet. It wasn’t always just for fun. Anagrams were originally seen as divine hidden messages from the gods.

Anagrams could cause wars. According to The Puzzle Instinct by psychologist Marcel Danesi, Alexander the Great once had a dream about a “satyr,” the mythical character that is half-man, half-goat. Alexander was troubled by the dream. What did it mean? He asked his soothsayers, who wisely pointed out that, in ancient Greek, the word for “satyr” is an anagram of “Tyre is yours.” (Tyre was a city Alexander’s army had surrounded). Alexander took this as a green light from the gods. He invaded Tyre and made it his. Admittedly, Alexander might have found another excuse to invade if not for anagrams. He was a big fan of invading.

Another anagram was at the center of a famous seventeenth-century trial. A British woman named Eleanor Davies claimed God had anointed her prophet, pointing out her maiden name is an anagram featuring another prophet: “Reveale, O Daniel!” She was put on trial for blasphemy, and her prosecutor argued that the name Dame Eleanor Davies is an anagram for “Never soe mad a ladie.”

Notice that anagrams were a lot easier before spelling was standardized.

Humans, apparently, love searching for hidden meanings. We love to believe that there is something just under the surface, that all is not what it seems. We find patterns in the noise, the face of Jesus in a slice of French toast. Psychologists call this tendency “apophenia.” And anagrams play right into that weakness. (I’ll talk more about the downside of puzzles later.)

When they were not causing wars or convictions, anagrams were seen as an art form. The word “anagrams” itself is an anagram for “ars magna”—the “great art”—so there’s your proof right there.

A lot of brilliant minds spent their days rearranging letters. Consider Galileo. He announced several of his discoveries—such as the existence of Saturn’s rings—by hiding the information in complicated anagrammatic poems. His fellow scientists had to decode the poems to reveal Galileo’s latest insight. You ever wonder why no one came to Galileo’s defense during that heresy trial?

In the seventeenth century, King Louis XIII of France appointed a man named Thomas Billen to be his Royal Anagrammatist at a salary of 1,200 livres a year. Billen’s entire job was to fashion sycophantic anagrams, rearranging the letters in royal names to create flattering descriptions.

The Victorians also liked their obsequious anagrams.

Lewis Carroll famously created this one out of Florence Nightingale:

Flit on, cheering angel 

But anagrams can also be a weapon, the nerdiest form of insult humor ever invented. Consider the surrealist painter Salvador Dalí. His detractors claimed he was a sellout and called him “Avida dollars,” which translates to “Eager for dollars.”

And in 1936, the New York Times reported that

Mother-in-law

is an anagram for

Woman Hitler.

The Hitler joke—which has obviously aged poorly for several reasons—appeared in an article about the annual meeting of the National Puzzlers’ League, where it was awarded the anagram of the year.

It turns out, the National Puzzlers’ League still exists and is still the source of the greatest anagrams on the planet. Founded in 1883, with a current roster of about seven hundred members, the NPL is the oldest puzzle society in the world. Every month, it publishes a magazine called The Enigma filled with anagram-based puzzles. The Enigma has a tiny circulation and low production value—it’s a couple of dozen pages stapled together—but it contains brilliance. I started receiving it several months after joining the NPL (a $30 annual fee). At first, the puzzles seemed impenetrable. So I decided to get a tutorial from a fellow NPL member whom I’ve known for several years: Mike Reiss, a longtime writer for The Simpsons.

I visit Reiss at his midtown Manhattan apartment. He loves New York, and refuses to move to Los Angeles, instead commuting weekly during the writing season.

Mike’s apartment is home to a collection of Emmy statues, a framed platinum album of The Simpsons Sing the Blues—and lots and lots of puzzle books. Puzzles, he tells me, are his greatest passion.

“My mind is always going. I tried meditation a couple of times. But when I try to meditate I think I’m going to lose my mind, because I’m just sitting there going, ‘I’ve got a million things to think about.’ That’s what I like about puzzles. It’s like: ‘Here’s something for your brain to be doing.’ It’s a relief to have someplace to put my mind’s energy.”

Mike says several other Simpsons writers are puzzle addicts and won’t start writing the episode until they’ve solved their fill. “My boss will say, ‘Um, we’re supposed to be working.’ And I just think, ‘Well, puzzles take precedence.’ ”

But Mike thinks humor and puzzles are related.

“So many of my favorite jokes are actually puzzles, and more precisely algebra problems: you have to solve for the missing element x, where x = the comedy,” he says. “For instance, ‘The towels in this hotel are so fluffy, I can barely close my luggage.’ The joke is he’s stealing towels, something never mentioned anywhere in the joke.”

I think it’s true: humor, puzzles, and math are all close cousins. “Or then there’s this joke, that’s even more like a puzzle, where you can watch the hearer pause to solve the joke,” says Mike. “A skeleton walks into a bar and says, ‘I’d like a mug of beer and a mop.’” 

Mike likes all kinds of word puzzles—crosswords, cryptics, riddles— but he’s a compulsive anagrammer. It’s almost a disease, he says. He can’t see a word without rearranging the letters. For instance, when he looks at a bottle of vodka, he recalls that Stolichnaya can be shuffled to read “satanic” and “holy” (near antonyms). Sometimes he’ll speak in anagrams and not realize it till later, like the time he and his wife saw a Noel Coward play, and Mike was not impressed. He said to his wife, “Noel Coward is no Oscar Wilde.” He later realized “Noel Coward is” anagrams to “no Oscar Wilde.”

He’s had this talent/curse from childhood. “I have monocular vision—no depth perception. The whole world is flat. My mom thought that was why I’m so good at jumbling letters.”

Not coincidentally, anagrams have often appeared in The Simpsons. In one episode, Bart rearranged the letters on a sign that said “Garden” to read “Danger.” In another, he switched the sign for “cod platter” to read “cold pet rat.” (Not to mention that Bart is an anagram for Brat. Reiss says he wrote a reference to that into the very first episode, but it was edited out.)

I don’t suffer anagram-itis as much as Mike does, but I’ve caught the mild version of it since I began doing the Spelling Bee. I anagram while waiting in line, while brushing my teeth, and, unfortunately, while driving. That’s an interesting sign, I’ll say to myself. “Yield” contains “deli,” “lied,” “idle.” Also, “die,” which is what I might do if I don’t pay attention to the road.

Mike has a stack of Enigmas, and we take one out and sit on his couch. Each issue has several types of anagram-inspired puzzles. The first type is just a straight-ahead anagram. Reshuffle the letters to discover an answer that relates to the phrase.

Here’s a classic from an Enigma from 1898:

HEY, DOG, RUN!
which rearranges to “Greyhound.”

And another from 1921:

ENSLICED EATS
which rearranges to “Delicatessen.” 

A more recent one:

LATTES? IN HASTE, GO NW
which rearranges to “Seattle, Washington.”

Beyond the Anagram

The anagram is just the start. Other word puzzles in the Enigma are even trickier. But to explain those, let’s go to Colorado.

Every year, hundreds of puzzlers meet in a different beautiful city for the National Puzzlers’ League convention. In summer of 2019, I attend the convention in Boulder, Colorado, home to stunning mountains and gorgeous bike trails. Neither of which I got to see, since I spent the weekend in the hotel ballroom with my head buried in puzzles.

When I arrive, the first thing I experience is clipboard envy. We’ve been told to bring clipboards for the sheets of puzzles that are handed out. My clipboard is fine but pretty boring compared to those of some puzzlers, which are tricked out with built-in compartments for pencils and erasers.

I check in at registration, using my nom de puzzle. Every member of the NPL has their own clever and/or nerdy pseudonym. Will Shortz’s nom is “Willz.” It’s a rebus: “Will short z.” He knows what he’s doing.

My nom is less clever, but meaningful to me: 1-Down Saturday, a reference to my appearance in the Times crossword.

The night I arrive, there’s a tutorial for those who want to learn about the NPL’s trademark word puzzles that appear in The Enigma. These puzzles are called “flats,” and were invented by the NPL way back in the 1800s. You can find a full explanation on the NPL website, but for a simplified summary:

A flat consists of a poem with blank spaces for the answers. The answers are two or more words that are like anagrams on steroids. They come in various types. There are puzzles in which you remove a letter from the beginning of a word to produce another word: “Factor” becomes “actor.” That puzzle goes by the gruesome name of beheadment.

There’s another type of puzzle where you remove a word’s last letter: “Aspiring” becomes “aspirin.” That one is called curtailment.

My tutor is Guy Jacobson, a longtime contributor and editor at The Enigma (who points out that my last name is a two-letter curtailment of his).

“There are dozens of types of flats,” Guy says. “There’s one called ‘Spoonergram,’ and another called ‘Baltimore Transdeletion.’ It’s a whole thing.”

The flats are hard to solve, and even harder to write. You have to look for fresh wordplay, which is an increasingly rare creature. Guy talks about the thrill when he discovers a new anagram or beheadment. “It’s like discovering a new species of owl, or a cure for dis- ease,” Guy says. And he speaks with awe about one of his all-time favorites, discovered by an NPL friend:

Take the word for Spanish sausage:

Chorizo.

Add a letter to the end and get:

C Horizon (a geology word for a certain level of soil). Add a letter to that and you get:

Chorizont.

Perhaps you don’t know the word “chorizont.” I sure didn’t. Well, a chorizont is a person who believes that The Odyssey and The Iliad were written by two different people.*

What a time saver! I can’t tell you how often I’ve been chatting with someone and had to say the clumsy phrase, “Oh, she believes The Odyssey and The Iliad were written by two different people.” Now I can just use that one word, chorizont! Another great life hack!

I tried a couple of flats, and they are hard. But I did crack some of them after half an hour. And when I did, I experienced two emotions: joy and annoyance. Joy that I saw that “Kalamazoo” and “Lama kazoo” were related, and annoyance that it took me so long.

Guy says this exact combination of emotions is what the puzzlemaker wants to evoke in you.

“When someone solves a flat, they should feel proud of themselves, but also ashamed. The puzzlemaker wants to use a connection that’s already in the solver’s brain but in some corner so that when they actually stumble upon it, they go, ‘Oh, that’s so cool. Why didn’t I see that? Shame on me.’ ”

After three days, it’s time to leave Boulder. Which, as one attendee pointed out, is a homophone for “bolder,” and which is what he hopes I have become in terms of solving puzzles. An appropriate ending to my trip.

*The word “chorizont” is sometimes used in a more general sense to mean some- one who challenges the authorship of a work. But I prefer the original and unadulterated meaning.

___________________________________

Excerpted from The Puzzler: One Man’s Quest to Solve the Most Baffling Puzzles Ever, from Crosswords to Jigsaws to the Meaning of Life by A.J. Jacobs. Copyright © 2022. Available from Crown Publishing Group, an imprint of Random House, a division of Penguin Random House, LLC.

A.J. Jacobs

A.J. Jacobs is a journalist, lecturer, and human guinea pig who has written four bestselling books—including Drop Dead Healthy and The Year of Living Biblically—that blend memoir, science, humor, and a dash of self-help. A contributor to NPR, The New York Times, and Esquire, among other media outlets, Jacobs lives in New York City with his family.