The IBA official cocktail list is the kind of list that has its own Sporcle quiz and its own Wikipedia article—an “IBA official cocktail” label even christens the top of each cocktail’s own Wikipedia infobox:

As of 2025, there are 102 IBA official cocktails, and as of July 12, 2025, I’ve had every one of them.

The journey has taken me to some interesting places, and now that it’s done, I have a little story to tell for each cocktail. I’m not gonna tell you all 102 stories, but I do want to debrief the experience. Drinking all 102 cocktails turned out to be unexpectedly tricky, and for reasons you’ll soon understand, I might be one of the first people in the world to do it.

⚠ Drink responsibly!

This endeavor involved drinking a lot of alcohol, but I did it over the course of a few years. It’s rare that I have more than a drink or two in one night (and never have I ever blacked out from drinking).

I do not recommend speedrunning the IBA official cocktail list. It’s important to know your limits, be conscious about how much you’re drinking, and drink a lot of water. If you’re struggling with an alcohol addiction, you should probably stop reading this post and talk to someone (if you’re outside of the US, you can find a helpline here).

How it started

I’m something of a list keeper. But it can be hard to decide when to start keeping track of things. So sometimes, I pick an arbitrary starting point that feels vaguely fateful, and I keep a list from that point on. For albums, it was the day I got my AirPods Pro delivered. For restaurants, it was the day I moved to New York City. For cocktails, it was the day I turned 21.

I started a note in Obsidian called Legal Cocktails, enumerating each type of classic cocktail I had consumed since I came of age. A dry martini at 5801 to usher in my birthday. A sex on the beach on an intern dinner cruise a couple weeks later.

Over the next couple years, Legal Cocktails grew to about 50 different drinks. Throughout my senior year at Illinois, my more epicurean friends Aidan and Christian would host a series of little get-togethers where they’d mix us drinks in their apartments, ranging from more pedestrian picks like the daiquiri and negroni to deeper cuts like the hanky panky and a half-decent Ramos gin fizz Christian made from melted butter.

First semester that year, I took a Beverage Management class, which was ostensibly about managing bars, but it was no secret that everyone took it because of its tasting component. The very last lecture focused on cocktails, and the tasting section featured an old fashioned, martini, margarita, whiskey sour, and the new-to-me Planter’s punch—not bad for a college class. And through it all, I was sometimes a normal college student, drinking Long Island iced teas at Legends happy hour and shitty tequila sunrises at Red Lion (I regret to inform you I deemed the Kams Blue Guy too proprietary for my list).

Some time after graduating and moving to New York City, I began to reckon with Legal Cocktails. What really counted as a “classic” cocktail? Where do I draw the line? It felt a little arbitrary. So on May 9, 2024, I decided to retcon the list into a checklist, and nix the “legal” requirement (something something statute of limitations). I had heard of the IBA official cocktail list from my time on Sporcle and Wikipedia, so it seemed like as good a list as any to base mine on.

At that point, there were 89 IBA official cocktails, and I had tried 33 of them (a bunch of the ones on Legal Cocktails weren’t IBA official, like the Jägerbomb and, weirdly, the amaretto sour). One thing was clear: I had a lot of drinking to do.

Anatomy of a list

The IBA official cocktail list has existed for over 60 years. It was first proposed in Paris in 1960 by bartender and IBA founding member Angelo Zola, who felt the need to standardize the mess of cocktail recipes that differed depending on which bartender you asked. Zola assembled a committee within the IBA, and together, they decided on a set of cocktails that best represented the most important recipes served around the world.

The following year in Oslo, Zola’s vision became a reality, and the inaugural list was unveiled. It comprised 50 cocktails, many of which remain on the list today, but some of which (like the zaza) have gone by the wayside. That’s because the list has gone through big revisions every 10 years or so, with the IBA adding drinks they deem newly relevant and removing ones that have fallen out of fashion. (The 89-cocktail list I based my checklist on was established in the 2020 update.)

There are many ways one might organize a list of cocktails, but the IBA chooses to group them into three categories: the Unforgettables (these are all-time classics, like the Manhattan and the uhhh monkey gland), the Contemporary (these are newer, but have solidified classic status, like the Mai Tai and the Moscow mule), and the New Era (these are rising stars invented in the late 20th or early 21st century, like the espresso martini and the paper plane).

Most of the list comprises pretty normal cocktails that a good bartender would recognize. But some immediately struck me as esoteric, or hard to obtain for one reason or another—like the Canchanchara, which calls for Cuban aguardiente; the Spicy Fifty, an oddly specific recipe with red chili pepper in it; and what I saw as the final boss of the list, the Ve.n.to, with its arcanely formatted name and a recipe centered on grappa and a hyper-specialized “chamomile cordial.” All of them, nonetheless, had a Wikipedia page (no matter how small), their inclusion on the list alone serving as a badge of legitimacy.

I was slightly convinced the Ve.n.to was planted on the list by Big Grappa, and as far as I could tell, it was only served at one bar in middle-of-nowhere Italy (the Spicy Fifty, one in London). But I had a list to complete, and nothing was gonna stop me.

Smooth sailing

For a while, checking cocktails off the list was easy. It was just a matter of going to bars and restaurants (which, like any other yuppie, I was already doing), scanning the menu, and hoping to find a classic cocktail I hadn’t yet tried. A boulevardier at Kelly’s. A Champagne cocktail at Antler (one of my early favorites, a nice blend of bitters and bubbles).

A formative moment early in the quest came at Uncle Charlie’s Piano Lounge in Midtown with Ming and Alina. A divey gay bar with no menu? Sounded like a perfect opportunity to check off some drinks! I scanned through my list to find something simple to try and order, went up to a mustachioed bartender, and asked, “could you do a caipirinha?” He replied, “nah, we don’t have cachaça”—a reality check—and I said, “alright, I’ll just do uhhh an Aperol spritz” (one of my old reliables).

After crushing my spritz, I went back to the same bartender. Still determined to check some boxes, I asked for a mint julep. “I’m afraid we don’t have mint,” he laughed, “you fancy boy!” Unwilling to settle for another spritz, I scurried back to Ming and Alina and asked them what to do. Alina suggested, “why don’t you just show him the list and see what he can make?”

So that’s exactly what I did. Back at the bar, I briefly explained my mission to the bartender, handed him my phone, and he scrolled through the list. “Oh, I can do a few of these,” he said, “You’re cool with any of them?” “Yeah, whatever you can make,” I replied. Soon enough, I had a lemon drop martini in hand. (Alina tried mine and then ordered one for herself, but the bartender asked her, “Is that for your friend or you? If it’s for your friend I’ll make him something new!”)

After gleefully finishing the lemon drop (and singing “Y.M.C.A.” at the mic), I returned to the bar one last time. The bartender greeted me, “What’s next for you, fancy?” I handed him my phone again, told him to “surprise me,” and emerged with a New York sour, which he explained was basically a whiskey sour with a red wine float. Sometimes all you have to do is ask.

On our way out that night, the bartender bade me farewell—”bye, fancy!”—and I had a new favorite service experience of my life.

Monkeying around

The monkey gland, that one odd duck in the Unforgettables section, was my white whale for a while. Obscure even to a seasoned bartender, it taught me that you can’t go ordering every drink on the list willy-nilly. At another dive, my friend Michael went up to the bar and asked point-blank, “two monkey glands, please!” You could imagine the bartender’s confusion.

A month or so later, at Gage & Tollner with fellow cocktail enjoyer Malaika, we were bantering with the bartender about my list. He had also never heard of the monkey gland, but he was curious, so we explained it to him, and the conversation moved on.

Just as my rusty nail and Malaika’s French 75 neared completion, the bartender plopped down two cocktail glasses in front of us, each half-filled with a pinkish-orange liquid. “Two monkey glands,” he declared.

They were pretty good—the orange and anise flavors complemented each other surprisingly nicely, but also, they were free, which makes everything taste better.

London calling

I kept cruising through the list. A naked and famous at Death & Co. (where the naked and famous was invented). A Clover Club at the Clover Club (where, I learned, the Clover Club was in fact not invented).

Then in November, I was in London for a two-week work trip. This would mark a significant turning point in my journey, for multiple reasons.

For one, I was able to check off the Spicy Fifty, one of the list’s most perplexing inclusions, by going to creator Salvatore Calabrese’s own Velvet bar at the Corinthia hotel, seemingly the only place in the world where it’s served. The bar was truly posh—before I had my drink (which was great, though I kinda wished it was spicier), I was greeted with a complimentary tray of candied almonds, olives, and blue corn flatbread. But this luxury was juxtaposed with an extremely cursed cocktail menu, featuring an AI-generated image for each drink (and one AI-generated Nelson Mandela quote):

I hit up the American Bar at the Savoy Hotel, London’s oldest extant cocktail bar, for an angel face (which was invented there) and a painstakingly garnished horse’s neck. I got a corpse reviver #2 at the confusingly similarly named Bar Américain. Turns out “American bar” just means a cocktail bar, as opposed to the city’s many beer-centric pubs, because cocktails are an American invention. That’s what I call a cultural victory.

But the most important bar on this whole journey, and my new favorite bar in the world, was Satan’s Whiskers in London’s Bethnal Green neighborhood. I went there on a whim, per Malaika’s recommendation, not realizing it would be a godsend for someone trying to complete this list.

The thing about Satan’s Whiskers is that their printed menu, focused on classic and modern classic cocktails, completely changes every day. This means the bartenders have an encyclopedic knowledge of the cocktail canon, and they have the ingredients on hand to make any of the 900 drinks they rotate between.

At first, I scanned the menu and didn’t see anything I needed for the list, so I panic-ordered a Jungle Bird (which wasn’t on the list, but I had heard of it—it was great). Then I decided to venture off the day’s menu: “Do you know a… brandy crusta?” Without hesitation, the bartender Ollie said, “sure, I can do that!” and confirmed I wanted a sugared rim. Next, I had a Tipperary, which he explained was an odd flavor combination that they’d only really list on their menu on an unpopular day (Mia, another bartender walking by, chimed in, “Tipperary Tuesdays!”). I capped off the night with an Alexander—​“gin or brandy?”—a brandy Alexander, which made for a perfect dessert cocktail. It all felt unreal, like a bar created in a lab for the sole purpose of me finishing this list.

A spanner in the works

A couple days later, I was checking in on the IBA official cocktail list website, and I could not believe my eyes. There were new cocktails on the list.

It felt like a bad dream. Still in an unfamiliar city, having just been to this magical bar, now confronted with these freaky new cocktail names on a list I had grown so accustomed to. Wasn’t the last update only a few years ago? (Since then, I’ve had several actual nightmares of the IBA adding anywhere from a few to a few hundred new drinks to the list.)

To be precise, there were now 102 IBA official cocktails, up from the previous 89. 3 had been removed from the list (including the golden dream, which I had gotten at Attaboy, long live the golden dream), and 16 new ones were added (including the Jungle Bird I had just had at Satan’s Whiskers, nice). I coped by tweeting through it, seemingly the first person on the internet to discover the update.

In reality, and I only learned this several months later, the day I discovered the update was the exact same day it was added to the IBA website. What I didn’t know was that there had been news articles about the update 8 months earlier, but they were all in Italian because the update coincided with a new 101 IBA Cocktails book, published exclusively in Italian for whatever reason (the book inexplicably leaves out the fernandito, fernet and Coke, maybe because 101 sounds more fun than 102).

It was no longer true that every IBA official cocktail had its own Wikipedia page. A few of the new ones did, like the sherry cobbler, the porn star martini, and the South Side (which had previously been added and removed from the list), but now the list was sprinkled with red links. Most of the new ones were pretty legit modern classics, but one stuck out like a sore thumb.

It was called, bafflingly, the IBA Tiki. A Google search revealed almost no information about it. Its recipe had 9 ingredients, including gengibre (just Portuguese for ginger) and two specific Havana Club rums, which are illegal in the United States thanks to Cuban sanctions. Step aside, Ve.n.to, there’s a new final boss in town.

I later learned that the drink’s recipe was commissioned by the IBA for their 2022 World Cocktail Championship, which was held in Cuba and, naturally, sponsored by Havana Club. For some reason, they saw fit to make it cocktail number 101 in their 101 IBA Cocktails book, and now it’s forever enshrined in cocktail history.

***

That night, I did the only thing I could do, and I went back to Satan’s Whiskers. In fact, I ended up going there four nights that week, checking off an obscene 13 cocktails within their taxidermied walls. The bartenders had, obviously, never heard of the IBA Tiki (and didn’t have those rums on hand), but they knew plenty of the other new additions off the dome.

It was also there that I discovered my love for the Porto flip, the only IBA official cocktail to contain egg yolk. I wasn’t sure if Satan’s Whiskers would be able to make one, but Mia’s face lit up when I ordered it—she had a soft spot for flips, and once I took a few sips, I knew it was one of my new favorites too. (On the Sporcle quiz, the Porto flip currently sits as the single least-guessed IBA official cocktail.)

I left London with a new favorite cocktail, a new favorite bar, and a napkin listing 6 bars Mia recommended in NYC.

82 down, 20 to go.

The final stretch

At this point, it was exceedingly unlikely to stumble upon the remaining cocktails on a bar menu. It was now a matter of seeking out particular bars that offered each drink, or failing that, going to really good bars and hoping they could whip one up.

Such was the case with one new addition, the Brazilian rabo de galo (literally “tail of the cock,” or “cocktail”), which I ordered off-menu at the bitters bar Amor y Amargo to excellent effect—I’ve since had two more of them at actual Brazilian restaurant Berimbau, and I’d easily place it next to the Porto flip as a favorite on the list.

I knocked out the Canchanchara at The Rum Bar BK, which miraculously had one on their menu. I got the new Chartreuse swizzle and pisco punch at the ice-obsessed Dutch Kills, which captures the Satan’s Whiskers magic as well as any bar I’ve been to in New York City.

I was this close to booking a trip to Italy for the Ve.n.to, when suddenly, googling “chamomile liqueur nyc,” I came across Santi, a new Midtown Italian restaurant that just so happened to have the exact right grappa and chamomile liqueur on hand. I went there with Alina, and the bartender, Emanuel, had never heard of a Ve.n.to, but he was determined to make me one—he even went on a wild goose chase to fetch a grape from the kitchen as a garnish, before coming back with some delicious vanilla poached pears. Impeccable service, tasty drink, and cheaper than a flight to Italy.

The last several drinks were more of a crawl than a sprint, many of them an exercise in explaining the recipe to a bartender in the least annoying way possible. An improvised paradise at Montréal’s Cloakroom. The very obscure Don’s special daiquiri at Paradise Lost. A Russian spring punch, a British creation I really should’ve gotten at Satan’s Whiskers, at Dear Irving.

And then there was one.

Let’s have a Tiki

Up until this point, I had acquired every cocktail by ordering it at a bar (or a makeshift bar at a friend’s apartment). But for the 102nd and final cocktail, the IBA Tiki, that wasn’t gonna work. Too obscure, too many ingredients, rums too illegal in the United States. So I took matters into my own hands.

The plan: gather all the ingredients, batch-prepare some IBA Tikis, and throw perhaps the world’s first IBA Tiki party. Incidentally, my 24th birthday was quickly approaching, so I even had an occasion for the celebration.

The rums, of course, were the hard part. I can’t exactly explain what I did in a blog post, but let’s just say we were about to have some of the most faithful IBA Tikis that had ever been made in the United States. (Shoutouts to my mom and my sister, who both played instrumental roles in the operation.)

The rest of the ingredients were straightforward enough. Amaretto, check. Luxardo maraschino, check. Frangelico (hazelnut liqueur, which the IBA Tiki is the only IBA official cocktail to include), check. The juices and purée and gengibre, check. All that was left was to put it all together.

And so I did. On Saturday, July 12th, 2025, my 24th birthday, about 20 people gathered in a modest Brooklyn apartment. For the crowd, we prepared an industrial-sized IBA Tiki in the vessel of choice, a borg. But for my personal drink, I mixed it myself using a cocktail shaker my mom got me for my birthday, and I served it for myself in a highball glass. After carefully garnishing the cocktail (for the Wikipedia picture) and making a speech to the attendees, it was time to drink it.

The IBA Tiki was great. Everyone agreed it was great. It was sweet, sour, nutty, and gingery, and we went through two full borgs of it. It may be a completely contrived recipe, and it may or may not deserve to be on the list, but one thing’s for sure: it was a fitting end to the journey.

Closing time

102 cocktails, 7 states, 3 countries, and 1 surprise update later, my work here was done. But you can’t drink 102 cocktails without learning a few things along the way.

One thing I learned is that the IBA official cocktail list is a weird list. But that’s probably bound to happen when you try to represent the whole world of cocktails in one list. The list might be a helpful guide for a bartender aiming to be well-rounded, but in a practical sense, for normal people just going to bars and ordering drinks, it’s not all that useful.

So from my research and my interactions with dozens of bartenders, I recategorized the list into a spectrum based on name recognition and ingredient availability. It’s probably an oversimplification, and the perspective is definitely US-centric, but I think it makes for a good starting point if you’re wondering what to order:

Between the Canchanchara, IBA Tiki, Spicy Fifty, Ve.n.to, and the relative obscurity of several others, you really have to be trying hard if you want to drink all 102. As far as I could find, no one else online has done so, at least not since the update that brought the IBA Tiki along. (It seems possible that someone high up at the IBA has tried one of everything, but I bet they made a lot of them themselves.) (Update after posting: it looks like some folks on Reddit have made their way through the list!)

When I first embarked on this journey, I didn’t really know what I liked in a cocktail. Now I know I like bitters, and egg whites, and silky, stirred drinks on a big rock. I’ve learned I have an affinity for Porto flips and rabo de galos. And I’ve learned that Satan’s Whiskers is the best bar in the world. (I also wrote its Wikipedia page, plus ones for the Jungle Bird, the Chartreuse swizzle, and the IBA Tiki. There’s still work to be done on many of last year’s additions!)

A common refrain at the IBA Tiki party was, “now that you’re done with cocktails, what’s next?” Well, I’ve gotten pretty good at drinking cocktails, but now that I have some mixology equipment, I might as well start making some. And while I’m at it, I can venture into the endless expanse of cocktails that aren’t on the IBA list.

I may be done with one list, but I’ll never stop checking boxes. I’m ambiently working my way through the NYT’s 100 Best Restaurants in New York City (18/100) and their 57 Sandwiches That Define New York City (18/57). I want to visit all 50 states (42/50) and all 63 national parks (12/63). Who knows, maybe I’ll try to pet every dog breed (???/292) or learn every tune in the Real Book (???/400).

But the IBA official cocktail list (102/102) is done and dusted. Until the next update, that is.

Square roots

We direct our attention toward the #etuiposting channel, Crosscord’s designated space for shitposting (so named because ETUI, a sewing case, is a prototypically shitty piece of crosswordese). There, one afternoon in January 2022, crossword constructor and Crossword Nexus warden Alex Boisvert posted what seemed at the time to be an innocuous, mildly interesting observation:

Suffice to say, the Crosscord hivemind had other examples of this. Will Nediger replied a few minutes later with the clever MULTITOOL and MULTIPLIERS (words with completely unrelated meanings, despite the fact that PLIERS are a TOOL). Several messages later, Alex chimed back in with the elegant PUB QUIZ and BAR EXAM, a pairing that had been used in some form in crosswords by constructors Christopher Adams (2018) and Robyn Weintraub (2021).

Something about this concept—two sets of synonyms (PUB and BAR, QUIZ and EXAM), which when paired together, form phrases that themselves are not synonyms (PUB QUIZ and BAR EXAM)—captured the minds of Crosscord. Suddenly, the floodgates were open.

Intermittently over the next year, #etuiposting would be flooded with these pairs of pairs. They became too much even for the shitposting channel, and were ultimately confined to a thread called #double-doubles (a name Bob Weisz and I both proposed simultaneously). Today, more than three years after Alex’s original prompt, the thread still remains active, a wordplay oasis of over 3,000 posts.

There’s something going on here. Something more than a shitpost or an ephemeral trend. Double doubles have the proverbial juice, and the juice lies in their structure. Each pair of pairs can be modeled as a square, where the corners are words and the sides are relations between those words:

It’s this square structure that makes each double double feel tight, feel satisfying, feel like a real “find”. This is the essence of what I’ve started calling square theory, and it applies to much more than just posts in a Discord server.

Just like it’s satisfying when an essay or a news story comes full circle, or mindblowing when you find an unexpected cycle in your network of friends, it’s inherently compelling when things wrap around and complete the square. Let’s break it down.

The theory of everything

Crosscord wasn’t the first to catch onto this kind of formation: Ricki Heicklen has maintained a huge list of double doubles (which she calls “Unparalleled Misalignments”—itself a sort of double double) since 2018, and the success of her recent Twitter thread about them is another testament to their widespread appeal. Pairs of the same form pop up on a regular basis in the form of crossword clues and Twitter jokes:

However, there’s nothing about the square structure that dictates the edges must represent phrases and synonyms. Each edge of the square can be any relation that connects its vertices (but generally, the stronger the relations, the stronger the square). The vertices don’t even necessarily have to be words—they can be any entity or concept.

It evokes the mathematical field of category theory, which very abstractly studies mathematical objects and the relations between them. It’s the topology of the square that makes it satisfying, regardless of what the edges and vertices represent.

Members of the #double-doubles thread have already noticed this, consciously or not, with many of the posts interpreting the original prompt more liberally and swapping out the “synonym” relation for something else:

Sometimes it feels like the #double-doubles thread has devolved into just #question-mark-clues (crossword clues that are trying to trick you, requiring you to reinterpret them beyond their words’ most likely meaning, or “surface sense”). But that’s no coincidence—abstractly, every question mark clue takes the form of a square.

When brainstorming for question mark clues, crossword constructors experience this on a regular basis. You start with the answer at hand, playing word association with it in search of a combination of words that usually means one thing (the surface sense) but can be interpreted differently (the intended interpretation) to point to the answer, thus completing the square:

Take Will Shortz’s all-time favorite clue for instance, from a 1995 Martin Ashwood-Smith puzzle: [It turns into a different story] (which deviously didn’t even include the question mark). On the surface, “turns into a different story” typically means something like “develops into another situation.” But the intended interpretation takes the clue’s words to mean “rotates into another floor,” leading to the correct answer of SPIRAL STAIRCASE:

You might be familiar with this same sort of brainstorming if you’ve ever tried to come up with a clever title for a research paper, or an apt name for a company. There are plenty of names that might make you go “I guess that could work,” but it’s the square-completing ones that make you go “that’s the one,” or “that’s so good!”

One of my favorite examples of this is Brand New, the blog that catalogues the latest in corporate rebrands. Leave it to a branding blog to have a name this immaculate:

Even a seemingly straightforward brand name like Grubhub can exemplify the power of square theory. Presumably, Grubhub’s branding team started with a concept (a centralized app for food deliveries) and came up with a name that completes the square. But remove any edge of the square (besides the edge that dictates the app’s purpose), and you’re left with a name that only kinda works:

Aside from crossword clues and brand names, squares appear in the wild all the time in the form of jokes. There’s a vast universe of pun-based jokes (often in the form of dad jokes, or Twitter jokes, or Punderdome puns) that can be modeled as a square, where one side of the square is the contrived setup (“what do you call an X with a Y?”) that connects in at least two ways to the punchline (“an algebra problem!”) on the opposite side.

The strength of the joke rests in the strength of the setup, the punchline, and the connections between them—and if every side of the square is strong, you might have created something funny:

Getting into shape

You might be thinking: what’s so special about a square? What about triangle theory, or pentagon theory? (Or rectangle theory? Or rhombus theory? Okay, side lengths and angles don’t matter here.)

Well, it’s true that there’s something compelling about any loop-closing property, regardless of side count—a story that comes full circle is still satisfying no matter how many points it hits in between, and it’s still neat to discover a triangle of people who coincidentally know each other.

But here’s what I think makes squares special: a square is the simplest polygon that has non-adjacent sides. In a triangle, each side is adjacent to the other two sides. But in a square, opposite sides have no points in common, which makes any connection between them feel surprising, like a coincidence. In pentagons and beyond, this still holds, but the extra sides add complexity that make them feel slightly less elegant. Nevertheless, other shapes can be interesting too, but I see them as the exception, not the rule.

Remember Alex Boisvert’s original JET BLACK / JETBLUE example? Seems like it could be modeled as a triangle, right? Well, it turns out the “jet” in JET BLACK refers to the gemstone jet, which is etymologically unrelated to JETBLUE’s airplane jet, so it’s actually more properly modeled as a square:

Times square

Now that I’ve established that square theory applies to more than just crosswords, it’s time to talk about crosswords again.

It’s typical for American-style crosswords (à la New York Times) to have a theme, which will generally consist of the 4–6 longest Across entries in the grid, often including a “revealer” that ties the theme together. Nowadays, it’s common gospel among crossword constructors that themes should have some sort of wordplay-based connection—that is, a theme like “famous basketball players” or “brands of cereal” is unlikely to elicit a real “aha” moment from solvers, and thus unlikely to be accepted at major crossword outlets.

So what makes for a good crossword theme? Consistency is definitely key, and a notion of “tightness” is important too (the set of possible theme entries shouldn’t be too much bigger than the theme set that appears in the puzzle). But time and time again, I’ve noticed that what makes a theme really pop is—you guessed it—when it completes the square.

Take, for example, the Monday, February 17, 2025 New York Times crossword by Kate Hawkins and Erica Hsiung Wojcik, which features a great execution of a typical Monday theme type. In this puzzle, the seemingly unrelated theme entries SCRAPBOOK, POPEYES, UNDER PRESSURE, and GIDDY UP are united by the fact that they each end in an affirmative (OK, YES, SURE, YUP).

In a vacuum, this fact wouldn’t be that interesting, but Kate and Erica give the theme a raison d’etre with the revealer YEAH RIGHT, clued as [“Uh-huh, I bet” … or a literal description of what 17-, 24-, 36- and 50-Across all have]—that is, each themer has a synonym for “YEAH” on its “RIGHT” side. The key here is that YEAH RIGHT itself is an idiomatic phrase (meaning “Uh-huh, I bet”), and not just an arbitrary description of the theme mechanic, so it completes the square:

But it doesn’t stop there. Consider the Monday, February 18, 2019 New York Times crossword by Leslie Young and Andrea Carla Michaels. The theme entries here are NIGHT NIGHT, WHITE WEDDING, and MUSHROOM BALL (you know, like a vegetarian meatball), and the revealer, clued as [Graduation garb … or what the compound answers to 17-, 28- and 44-Across represent?], is CAP AND GOWN. That is, the first part of each themer can precede CAP (e.g. MUSHROOM CAP), and the second part can precede GOWN (e.g. BALL GOWN). This maps pretty squarely onto not one, but three squares, one for each theme entry:

And just for fun, we can conjoin the three squares by their CAP AND GOWN edges to form a unified graph that represents the entire theme’s topology:

The final crossword we’ll look at, and maybe my favorite crossword of all time, is Alina Abidi’s Wednesday, August 18, 2021 New York Times crossword, with a theme that feels almost impossibly tight.

The puzzle has essentially two theme entries, PIN THE TAIL ON THE DONKEY and WHITE ELEPHANT, with the apt revealer PARTY ANIMAL [Frequent reveler, or a hint to 16-/26- and 36-Across]. That alone is clever, since both themers are party games with animals in their names. But then Alina hits you with the second revealer of THOMAS NAST [Cartoonist suggested by this puzzle’s theme], pointing to the fact that not only are the DONKEY and ELEPHANT animals in party games, but they are also the animals that symbolize the Democratic and Republican parties, as popularized by Thomas Nast’s political cartoons.

This is the kind of theme that really sticks with you. Or at least it stuck with me, and I tried for years to understand why it felt so amazing. And then I realized square theory offered an explanation. Squares, as we know, feel tight, satisfying, and clever. But Alina’s theme takes that one step further, creating for each theme entry a square with an extra diagonal through it, reflecting the connection between each animal and a political PARTY:

And again, we can combine these two super-squares into one unified theme graph:

Granted, there’s more to a crossword than the structure of its theme, and it can be reductive to distill it into a graph like this. Still, for many puzzles, square theory can serve as an illuminating proxy for the intricacy and tightness of a theme. But that’s not all it can do.

Letter box

Let’s talk about Scrabble, one of the seven most important games out there. If you’ve ever played Scrabble (or similar games like Bananagrams), you’d know that every word you play has to intersect another word that’s already on the board.

But occasionally, you’ll think up a play that validly intersects not one, but two words on the board, forming a rectangle of words. Plays like this have a certain panache. They’re satisfying, they make you think, “ooh, nice.” And of course, they can be modeled with square theory:

You might be thinking that the edge relation here (a word that contains both letters) feels a little flimsy, since not every letter in the word is used. But what if every letter in the word was used? What if we could have a dense network of interlocking squares, where every letter was part of exactly two words? Well, we can, and it’s called an American-style crossword.

In American-style crosswords, every letter is mandatorily “checked” (part of an Across and a Down word), which means every letter is a vertex of a square:

If you’ve ever tried to construct a crossword, you’ll find that the framing of a crossword grid under square theory feels right. When you’re nearing the end of the grid-filling process, finding valid crossings of words to fill that final corner of a grid, there’s a satisfying “clicking” feeling—a sense of magic—when it all fits together, analogous to the wrapping-around feeling of completing the square.

Taking a step back, that means the clues, the themes, and the very grids of crosswords all share the same abstract fundamental structure, the square:

If you accept the premise that squares are satisfying, square theory offers a unified theory for why crosswords are satisfying too. And if squares are fundamentally compelling, the crossword, in its recursively square structure, starts to look like an equally fundamental art form. Like if you started an English-speaking civilization from scratch, someone, somewhere would inevitably reinvent the crossword. And then someone would start a crossword Discord server, and maybe they’d call it Crosscord.

It’s hip to be square

If you’ve read this far, I promise you’ll start to notice squares popping up all over the place in your daily life. I can attest, because I’ve been honing the concept for this post for about two years now, and I often find myself thinking “that’s a square!” whenever I come across a tight joke or title or crossword theme.

If you’re a creative person, square theory is a useful framework to keep in mind. If you’re coming up with a title for a paper or a brand name, try to see if you can think of one that completes the square. If you’re writing puns for a popsicle stick or a Laffy Taffy wrapper, you can use squares to model your setups and punchlines. If you’re constructing a crossword, consider whether your theme or your question mark clues can form squares.

And if you’re writing a story or a news article or a blog post, there’s fundamental value in making it come full circle, or perhaps full square.

Once you spend enough time with grids and clues in front of your face, everything becomes crosswords. You’ll hear a new phrase and think, “is that in my wordlist?”, you’ll see two words on a sign and think “these would stack well in a grid!”, you’ll start dreaming of theme ideas that seem genius while you’re asleep only to wake up and realize they make no sense. But every now and then these intrusive thoughts will yield a coherent idea for a puzzle.

One night this March, crosswords must have been permeating my consciousness as I was half-asleep, because I had a thought so intrusive that it catapulted me out of bed and onto my phone. At 12:57 am, I messaged my friends:

💭 Crossword calendar (each month’s calendar is a crossword grid where each day is a square)

Ok back to bed now

Eight months later, that idea has become a real thing—a physical object!—that you can buy right now and hold in your hands before the holidays. Introducing the 2025 Crossword Calendar:

2025 Crossword Calendar

It’s a folding wall calendar where each month is a crossword to solve, the grid taking the shape of the month’s calendar grid, with one letter to write in each day’s square. The grid squares are numbered like a regular calendar, with each clue enumerated by the day of the month its answer starts on.

The road from half-waking idea to physical object was a winding one, especially considering this was the first time I’d ever tried to create a real product that people can buy. Here’s how it went down (and across).

On the grid

The concept of a crossword shaped like a monthly calendar immediately poses a few questions.

1. What about the two-letter words?

In typical American-style crosswords, the minimum word length is three letters, because inaugural New York Times crossword editor Margaret Farrar said so. But some months start on a Friday or end on a Monday (like March, June, and August 2025), requiring two-letter words going across at the beginning or end of the month. So with regrets to Margaret, two-letter words are here to stay, treated no differently in the calendar from any other length word.

2. What about the unchecked squares?

Similarly, American-style crosswords don’t allow “unchecked squares”—squares that are only part of a word going in one direction and not the other. This means every square in a crossword is part of two words, so if you don’t know a clue going one way, you always have the crossing clues to help figure out each letter. This is also a Farrar-established rule, and it’s one of the key differences between American- and British-style crosswords.

Well, some months start on a Saturday or end on a Sunday (or both, in the case of November 2025), leaving an unchecked square in the first or last day of the grid. Rather than cluing these as one-letter words, which I think would have been a little confusing, I just made sure the words crossing the unchecked squares were both common (no names or obscure words that people might not know the unchecked letter of) and unambiguous (no clues like “Some Greek letters” for the entry _ETAS).

3. Isn’t that pretty hard to fill with words?

Pretty hard, but not impossible. My prevailing theory as to why seemingly no one has made a crossword calendar before is that filling a wide open 7x4-ish grid American-crossword-style is kind of a pain, and doing it 12 times is kind of 12 pains. With computer assistance, it’s pretty easy to fill a monthly grid with crappy words, but to fill one cleanly, with regular words that normal people know, it takes a lot of trial and error and/or an immaculately scored crossword wordlist.

Luckily, I’ve made enough crosswords at this point that my wordlist scores are refined enough and, crucially, I’ve become numb enough to the trial-and-error process, that making a grid for each of the 12 months didn’t strike me as too daunting of a challenge. The wide-openness of the grids wasn’t too dissimilar to some of the grids I filled for 7xwords, the project by Malaika Handa that enumerated every possible symmetrical 7x7 crossword grid.

So I just went ahead and did it. And yeah, it was kind of a pain, but after a few weeks I had 12 grids, one for each month, collectively filled with 365 letters, one for each day of 2025.

Really important calendar facts

Working on this project has given me a newfound appreciation for the shapes of calendar months. It’s pretty neat that every month has a unique shape—like a fingerprint—that defines the form its crossword must take. And since the number of days of the year isn’t divisible by 7, the starting day of each month changes every year, which means each month’s crossword grid is completely different depending on what year it’s for.

Calendarheads, tap in. Here are some facts about calendar shapes that are sure to go over well at parties:

• Monthly calendar grids usually have 5 rows, because most months have 30 or 31 days, which is a little more than 4 weeks. But if a 30-day month starts on a Saturday or a 31-day month starts on a Friday or Saturday, you’ll get an extra day or two at the end of the month, which necessitates a 6th row. It feels wrong that a month, which we think of as 4-ish weeks, could require 6 rows, but sometimes that’s just the way the cookie crumbles.

• Very rarely, a February will start on a Sunday, allowing it to squeeze onto 4 rows if it’s not a leap year. But it won’t be long—in 2026, the shape of February will be a perfect 4x7 rectangle. It’s gonna be a movie.

• I was curious if each month in a given year had a unique shape, or if there were any repeated shapes throughout the year. As it turns out, January and October are the only pair of months in 2025 with the same shape, since they start on the same day of the week and both have 31 days. This holds true every year, except for leap years, when January and July are the only twin months. This information feels a little bit cursed, since it’s always been true, but no one talks about it.

Putting it out there

Well now I had 12 little crosswords shaped like the 12 months of 2025, but the question still stood: what do I do with them? I basically made an ultimatum to myself: if I can’t find someone to publish the calendars for me, I’ll figure out how to do it myself.

My first thought was to pitch it to an existing calendar company, or maybe an existing crossword book company, and see if they’re interested in branching out to make my weird thing a reality. So back in March and April I tried floating the idea to a few places, but no one was biting.

Then I had a really silly second thought, which was to put all twelve months into one giant crossword grid and submit it to The New York Times as a Sunday crossword. Yeah, I was kind of sick and twisted for this, but if you put all twelve months together and pad them with black squares, they make this garish 23x25 grid with 142 words, which just so happens to barely exceed the typical Sunday size of 21x21 with 140 words.

Filled with words and clued with clues, it was a fully functional crossword, so in May, I went ahead and submitted it to the NYT just like any other puzzle. But you might be thinking this grid seems a bit unconventional for a NYT crossword, and you could not be more right—the NYT crossword submission specs list five “basic rules” for crossword grids, and this grid breaks all five of them:

• The grid has no symmetry.
• The white space of the grid is segmented into 12 disconnected sections, which means it does not have “all-over interlock” (side note: I’ve always thought “all-over interlock” was a super unintuitive term that requires clarification every time it’s said, but crossword people love to casually throw it around as if it makes perfect sense).
• The grid has five unchecked squares.
• The grid has three two-letter words.
• The typical Sunday grid has about 80 black squares, while this grid has uhhhh 210. But who’s counting!

For what it’s worth, any of these rules are allowed to be “broken with extreme rarity” if a theme calls for it—and I thought, hey, the theme calls for it. But suffice to say, a few months later, an email from the NYT crossword editors hit my inbox with regrets, concluding that “this would seem too much like solving 12 mini puzzles.” Can’t argue with that—12 mini puzzles is literally what this is, so they kinda nailed it. Maybe I should be the one sending my regrets to them for making them spend time reviewing the puzzle.

I could have tried shipping this Franken-grid to other crossword outlets, but I figured the NYT is generally the most flexible of the major outlets when it comes to funky rule-breaking grids, and it was go big or go home. So go home it was.

Bringing it home

With all my reasonable choices for external publishers exhausted, I pretty much had one choice left, which was to make the calendars myself. The obvious perk of doing it this way is that I have full control over the calendars’ design and editorial process, and the obvious drawback is that when it comes to publishing a physical product, I had no idea what I was doing.

So I asked some friends who do have experience making physical products (shoutouts to Parker Higgins, Taylor Tabb, Alice Getmanchuk, Matthew Sisson, and Leia Chang for their suggestions), discovered that print on demand is an industry that exists, found a provider that makes fully customizable wall calendars (Printify, which handles manufacturing and fulfillment), and finally made an online store with Shopify that integrates directly with Printify. I designed the calendars in good old-fashioned Photoshop, hand-placing every square and number and manually typesetting every clue.

And that brings us to today, when crosswordcal.com is a website on the internet where you can buy the 2025 Crossword Calendar for $20.25 USD. Many have been asking me, “Is next year’s gonna be $20.26? Isn’t that cheaper than inflation?” And to them I say, “I’m a man of the people!”

I might be biased, but I’d say the calendar makes an excellent gift for a word enjoyer—the puzzles are medium difficulty and designed to be beginner-friendly, so you don’t have to be a crossword expert to enjoy them. And again, biased, but I think it looks pretty neat on a wall.

Should you solve all the puzzles at the beginning of the year? Should you solve each one at the beginning of each month? Should you write in one letter a day? Should you just solve the one for your birthday month so you can see what letter your birthday is? Do whatever you want—I don’t make the rules, I just write the clues.

2025 Crossword Calendar

I had one such thought one night last May in my college apartment in Champaign, Illinois, and it followed me through graduation, into the summer, and to New York City, where over a year after conception, it became a real thing. It’s a game, and it’s called Sidle, and you can play it right now:

Sidle

Character development

Spoiler alert! The rest of this post will reveal a lot about the design and gameplay of Sidle, which I highly encourage you try for yourself before reading on!

I’m not sure how exactly the idea came to mind that fateful May evening, but I do know I must have been playing Wordle (which I should specify, for legal purposes, is not affiliated with Sidle). Like most people alive in the 2020s, I have a Wordle group chat—well, effectively it’s just me and my friend Ming sending our Wordle results back and forth, with our friend Art silently lurking as a courtesy to keep the chat a group chat.

Surely, Wordle wouldn’t be the viral sensation that it became if it wasn’t for its emoji sharing mechanism, producing a grid of colored emoji squares that reflect the game’s results, which can be conveniently copy-and-pasted and shared and spread like a yellow-and-green wildfire. And it’s from these squares that my idea arose: what if the yellow square was a little guy who could jump around on the green squares? And what if the emoji grid side-scrolled like a classic platformer game?

I often find that coming up with a good name for something is a huge motivator for making it happen. Well, once I thought of the name Sidle (“side-scrolling” + “Wordle”) (also just a word that means “move sideways”) (also five letters, like a Wordle answer), it wasn’t just an idea, it was happening.

You might be thinking that a platformer game seems pretty out-of-left-field coming from me, guy who makes crosswords and word searching tools and meme generators, but if you’ve known me for long enough, this should come as no surprise.

I’ve never been that much of a gamer, but I did grow up on simple, high-concept Flash platformer games like Shift, Tealy & Orangey, and This Is the Only Level. So ever since I started programming in middle school, making a platformer game myself has been something of a personal white whale.

From The Adventures of Orangle in middle school, which I made using Scratch with my friend Josh Tang, to lackluster attempts at rudimentary JavaScript platformers in high school, to a C++ platformer called Penguin Time in college (which is a pain in the ass to install, you’re better off playing Orangle, it still holds up), the allure of the platformer has followed me throughout my life as a programmer, with my every attempt getting most of the way to a coherent game but falling short in some way or another. As it turns out, for being so intuitive to play, platformers are deceptively tricky to develop.

Building blocks

They say form follows function. But in the case of Sidle, the game’s form largely dictated its function. Since I wanted the game to look like the Wordle emoji grid, much of the game’s functionality was locked in from the start:

• Every block would be aligned to a square grid, but the player would be able to move fluidly throughout the grid (in my original conception of the game, the player would only be able to move to discrete positions in the grid, but luckily I realized that those physics would look super choppy and weird).
• The visible window of the game would be 5x6 blocks (or smaller), leading to a sort of fog-of-war effect where the player can only see a small portion of the level at any given time.
• There would be no other types of blocks besides the player, the ground, and the background, since Wordle emoji grids only have three different color squares. This means no extra entities like enemies or lava or moving platforms.

Since I’m a sucker for simple, elegant games, I also decided from the start that there would be no death conditions, no wall-jumping, and no other controls besides moving left and right and jumping. And unlike Wordle, there would be no words involved (I know, it’s tough, I love words too). Constraints breed creativity!

Sidle’s only functional gimmick, which only materialized partway through the development process, was that on some levels, the player could consist of multiple yellow blocks, the same way a Wordle emoji grid usually has multiple yellow squares. These yellow blocks (called subentities in the code) would necessarily be controlled jointly by the arrow keys, but I had the choice to either make the subentities move separately and collide with their environment independently, à la Tealy and Orangey in Tealy & Orangey; or move jointly, as if they were connected by invisible rods.

I went with the latter, and it resulted in some implications that defined Sidle’s gameplay, especially in later levels where the player’s subentities are physically disjunct. It meant that the player’s collisions with the environment depended on an or operation on all of its subentities—a player made of two subentities is on the ground if one or the other subentity is on the ground. This meant that sometimes, instead of the player jumping from one platform to another, the platform sort of has to jump from one subentity of the player to another—an effect that becomes crucial in the last few jumps of level 10.

Technical difficulties

The game took over a year to develop, not because I toiled at it consistently for over 12 months, but because I worked on it in discontinuous bursts amid life changes and occasional bouts of frustration.

Fair warning, this section gets a little technical! If you don’t care about the technical details, feel free to skip to the last words.

I built Sidle in TypeScript and React, which is not a typical tech stack for a platformer game, but 1) I’m very comfortable working with it, and 2) it means the game can be a website, which means it can be played on any device with a web browser, without a finicky installation process (one of the pitfalls of my college-era platformer Penguin Time). I also used no graphics engine or game engine, opting instead to program the game’s animation and physics from scratch using the built-in JavaScript requestAnimationFrame() method, CSS top and left positioning properties, and some basic high school physics formulas for velocity and acceleration.

A wrinkle in time

There were two big wrinkles in the development process. The first was a direct result of my choice to eschew animation engines and rely entirely on the web browser’s built-in animation capabilities.

Because different browsers have different refresh rates, I couldn’t set the animation rate to a certain number of frames per second, and I couldn’t measure the player entity’s speed in pixels-per-frame. Instead, every frame, I had to measure the amount of time that had passed since the previous frame, and then calculate the player’s new position based on its speed in pixels-per-second. But since a non-whole number of seconds will pass between each frame, that means the player’s position will change by a non-whole number of pixels. This initially led to rounding errors that compounded over time and screwed up the physics, causing the player to occasionally clip into walls and fall through floors. Not good!

Many iterations and many long walks later, I landed on the solution to address this: keep track of the player’s position and unroundedPosition in tandem, where the unroundedPosition includes the precise non-whole number of pixels, while the position is pixel-perfect, and reflects the player’s actual visible position in the level. And if the player moves by multiple pixels from frame to frame, their position needs to interpolate to every pixel between the starting and ending point in order to check for collisions with blocks at every point. Much better!

A wrinkle in, uh, space

The other big wrinkle, which happened to be another pitfall of Penguin Time, involved the player traversing one-block gaps. Since all the blocks are exactly the same size, the player should consistently fall into a one-block gap, rather than gliding over it, particularly in cases where it moves multiple pixels in one frame (Penguin Time had the gliding issue, which I suppose is apt for a penguin). As it turns out, getting the player to move intuitively into one-block gaps in the floor and walls was a tall task, requiring lots of brainstorming and hard-coding behavior for particular corner cases.

Here’s a real sketch I made while trying to figure out which direction the player should go when it finds itself at the corner of a block. These cases ended up as if/else statements in the code almost verbatim:

When all was said and done, after several frustration-induced hiatuses, I had a fully functional, pixel-perfect, intuitive-feeling, home-cooked platformer engine. Sidle’s full source code is available here for you to peruse if you’re so inclined.

Last words

For something that started as a half-lucid idea, I’m truly happy with how Sidle turned out 13 months later. This game is a real testament to the “begin with the end in mind” principle (from this book, which I half-love and half-hate)—I started with a vision, and I spent the entire development process chasing the vision and trying to make it a reality.

If you’ve read this far, I think it’s safe to assume you’ve tried playing Sidle. I hope you enjoyed the gradual progression of levels, where each one gently introduces a new mechanic to the game. I hope my year of on-and-off development was worth it for your 5-minute or 20-minute or 1-hour reprieve from life. I hope you share it with your Wordle group chat and thoroughly confuse them. And I hope that next time you’re half-asleep and have a ridiculous idea, you consider writing it down.

Let’s play Scattergories, but instead of rolling a letter die, I choose the letter, and the letter is N. Quick, name one thing in each of these categories that starts with N:

That was… weirdly hard, wasn’t it? N gives off common-letter vibes—it’s one point in Scrabble, there are 8 of them in a Bananagrams pouch, it’s one of the RSTLNE letters on Wheel of Fortune—so by all accounts this should’ve been easy. So then what’s going on here? Why are all these super-normal categories so deficient in vitamin N?

Numbers

I know what you’re thinking: “Adam, you can’t just cherry-pick a bunch of categories to prove your point!” And you’re right! To do that, we’re gonna need to look at the data.

For this data analysis, we’re using the ENABLE (Enhanced North American Benchmark LExicon) wordlist, a free-to-use 172,000-word English dictionary that’s based on the Official Scrabble Player’s Dictionary but isn’t throttled to words under a certain length. You probably don’t recognize its name, but you may know its work—ENABLE is the base wordlist for Words With Friends and the default English dictionary on Wordlisted. It’s not perfect, but it’s a representative enough survey of English words for our purposes.

Also, we’re looking at the English dictionary in particular, not a natural language corpus, since we’re more concerned with how many different words there are rather than how often a given word appears. That means letters like T and H won’t be weighted for appearing in common words like the and that, meaning our letter frequency ranking will look a little different than rankings that take word frequency into account, like the classic Linotype ordering etaoin shrdlu.

So here are the letters of the alphabet ranked by how often they appear in the English dictionary. On the left is how often the letters appear overall, while on the right is how often they appear as the first letter of a word:

Immediately, you can see N plummeting: from the big leagues of overall letter frequency, down to the bowels of initial letter frequency, joining the likes of WVKJQYZX in the dregs of alphabet society.

Sidenote, it’s eerie how similar these two graph’s shapes are: despite having two completely different letter orderings, they both have three big leaders, six-ish more trailing behind, and then a steep dropoff into the long tail. Zipf’s law is crazy like that.

Here’s another way to visualize the same data, this time combining both distributions into one coordinate plane:

The dotted line here indicates where every letter would be if letter frequency was uniform throughout the word, i.e. if initial letter frequency was the same as overall letter frequency. So the farther a letter is from that dotted line, you could say the farther its initial letter frequency strays from expectation.

As expected, there’s the JQXZ crew hanging out at the bottom left, and S leagues ahead at the top right (thanks to plurals, and also just being an ultra-common starting letter). Way above the line, we see letters like P, C, B, and F, which are much more common as first letters than they are in general. Every vowel is below the line, which makes sense, since vowels are omnipresent but tend to be less common as starting letters. And then there’s N, the farthest consonant below the line, the most disproportionately rare starting consonant in the alphabet.

They don’t teach you this in school, folks. It almost feels wrong, like a forbidden piece of information, that N is such a rare first letter. So why might this be?

Nailing it down

Let’s consider a few prevailing theories, some combination of which explain why N is such an uncommon starting letter despite its overall commonness.

First, while N is undeniably a common letter in general, the bulk of its commonness is for reasons other than being at the beginning of words. Instead, its position in overall frequency rankings is inflated by the ubiquity of prefixes like un- and in-, as well as suffixes like -tion and -ing. In natural language, N’s frequency is further bolstered by its appearance in ultra-common words like in, an, and and. N is everywhere, but it’s not usually the letter in charge. In NBA terms, N is less of a star point guard and more of a reliable role player.

Second, N has less potential as an initial letter because of the lack of English consonant clusters beginning with N. Take a look at the most disproportionately common starting letters, the ones farthest above the dotted line of expectation: P, C, B, and F. They have one thing in common: they lead common consonant clusters like pr-, ch-, bl-, and fl-, giving them much more mileage in the initial position. But compared to all the cool consonants, N has nothing of the sort—the only words in the ENABLE wordlist that start with N followed by another consonant are nth, ngwee (1/100 of a kwacha, which is Zambia’s official currency), and ngultrum(s) (whaddya know, Bhutan’s official currency). Without consonant clusters, the priors for N as a first letter are lower, since there are fewer possible ways to construct a word starting with it.

Third, there is some historical phonological evidence that English words, especially nouns, have evolved away from starting with N. In English, we turn our indefinite article a into an when it’s followed by a word that starts with a vowel sound, enabling great jokes like “You’re going to Antarctica? Have an ice time!” But jokes aside, misunderstandings of N’s placement have led to the actual evolution of words as we know them today, in a process called faulty separation (also known as false splitting, a special case of rebracketing). For instance, an apron came from a misunderstanding of a napron, an umpire was once a noumpere, and an adder was a naddre. Granted, this transformation has also happened the other way around, turning an eft into a newt and an eke name into a nickname. Still, it’s likely that some of N’s unpopularity as a first letter was destined by a natural selection process—or should I say, an atural selection process.

Now what?

Now you know that N is a lowkey rare first letter, and you can tell your friends about it, and they can be like, “neat!” That’s pretty much it. I don’t know, did you think there would be some higher purpose to a blog post about the letter N?

I mean, if you’re making a crossword, be careful putting an entry with a bunch of N’s in it at 1-Across. If you’re writing an acrostic poem or an alphabet book, make sure you have something good for N before you get in too deep. And maybe, if you’re playing Scattergories and the die lands on N, roll again.

If you ask the university’s marketing office, their answer is perfectly clear: University of Illinois Urbana-Champaign. If you came here for a simple answer, there you go, but buckle up, because there’s a lot more to the story.

To truly understand the nuances of Illinois’s flagship university’s name and why people are so confused about it, we have to take a journey through 156 years of geopolitics, branding, and grammar.

Land of Lincoln

The year was 1867, and Illinois needed a new school. When Abraham Lincoln signed the Morrill Land-Grant Act five years earlier, the federal government granted every state a piece of land to establish a federally endowed university, and each state got to choose where to put it. The states also kicked out lots of Indigenous people in the process, which the universities occasionally acknowledge to this day.

After a bidding war, the humble town of Urbana won Illinois’s jackpot, and in 1867, a new land-grant university was born: Illinois Industrial University. It was founded in Urbana by academic warhorse John Milton Gregory, who was more of a liberal arts guy himself but called the university “industrial” to appease industry-obsessed lawmakers.

Gregory served as president of the university for 13 years until he tossed his papers into the air and resigned in 1880. Soon after, the university was beginning to realize it wasn’t just “industrial,” with burgeoning programs in agriculture, engineering, and Gregory’s favorite liberal arts. So in 1881, a year after Gregory’s resignation, students voted 250–20 to ditch the word “industrial” in favor of a new name. It took four years, but in 1885, the university finally changed its name to the more holistic University of Illinois, a name that stuck for a while.

John Milton Gregory died in 1898 and was buried next to Altgeld Hall on the university’s Main Quad. Legend has it, Gregory’s dying wish was to leave a modest legacy and have nothing named after him. So he’d be thrilled to know the university’s Department of History is now housed at Gregory Hall, which is a quick walk away from both Gregory Street and Gregory Drive.

A tale of two cities

It was the turn of the 20th century, and the University of Illinois was expanding. It was already leaking into Champaign, Urbana’s larger neighbor to the west, but it was time to go north.

In 1896, the Chicago College of Pharmacy joined forces with the university, officially becoming the School of Pharmacy of the University of Illinois. Over the next couple decades, the University of Illinois family also gained a College of Medicine and a College of Dentistry, both up in the Windy City.

Sometime around 1905, letters and publications from University of Illinois administrators gradually started including “Urbana” with the university’s name, probably to distinguish the university’s main campus from its growing medical presence in Chicago. This riled up citizens and business owners of Champaign, who wanted their name on the university that spilled into their city. Champaignians published multiple op-eds in local newspapers arguing that Champaign and Urbana should split the bill. Urbanans rightly pointed out that the bulk of the university was in Urbana, including its administrative offices (and thus the university’s mailing address).

The Urbana vs. Champaign debate heated up, and in September 1906, the university’s Board of Trustees held an actual meeting to resolve it. What came out of this meeting was the name “Urbana-Champaign”—with Urbana first and foremost, like the university itself. Soon after, “Urbana-Champaign” began appearing on official university correspondence, and over the course of the next few decades, it became a commonplace way to refer to the campus. But it wasn’t until 1969 that the university officially codified its new name, the University of Illinois at Urbana-Champaign.

The Illini Union, as seen from the Main Quad (in Urbana, not Champaign)

If you solved my latest crossword, or if you’re from the area, or if you know too much, you’d know that the metro area including the twin cities of Urbana and Champaign is called Champaign–Urbana (or C‑U, or Chambana, or Shampoo–Banana), not Urbana–Champaign. That’s because Champaign has pretty much always been more populous than Urbana, and metro areas are conventionally named with the more populous cities first, like Dallas–Fort Worth or New York–Newark–Jersey City.

So we have a university campus called Urbana-Champaign, in Champaign–Urbana. And you’re just gonna have to deal with it.

Drawing the line

You might have noticed another difference between Urbana-Champaign and Champaign–Urbana: Urbana-Champaign is written with a hyphen (-), while Champaign–Urbana is written with the slightly longer en dash (–). This isn’t a mistake, because if it was, I wouldn’t be pointing it out. So what’s going on here?

If you’re big into style guides, you might know that hyphens generally join two parts of one word or name (like post-punk or Anya Taylor-Joy), whereas en dashes join two associated but distinct things (like red–green colorblindness or the Spanish–American War). You can remember that hyphens are shorter, so they connect things more closely than en dashes do.

As far as I could tell, the campus name Urbana-Champaign has always used a hyphen in an official capacity, possibly because Urbana and Champaign are two continuous parts of one campus, or possibly because hyphens are easier to type than en dashes. However, this didn’t stop the Wikipedia article for the school from being titled University of Illinois at Urbana–Champaign (with an en dash), after a zealous editor decided it adhered to Wikipedia’s style guide in 2010. The article’s title stayed this way until 2021, when the hyphen triumphantly returned after a lengthy talk page discussion. As the user JustinMal1 put it, “In many ways, the campus is much like a marital union, and marital unions are hyphenated, not en dashed.”

The metro area Champaign–Urbana, on the other hand, takes an en dash, since Champaign and Urbana are two distinct entities that just so happen to be the metro’s two largest cities. Or if you’re typing on a typewriter, you’ll just have to settle for a hyphen.

Avengers assemble

Remember those medical schools in Chicago? In 1961, they officially became a new campus, called the University of Illinois at the Medical Center. Then in 1965, another Chicago campus was established, named the University of Illinois at Chicago Circle after a nearby freeway interchange. In 1982, these two Chicago campuses consolidated into the University of Illinois at Chicago (UIC), a proud member of the University of Illinois family.

And then there was little Sangamon State University, Illinois’s smallest state university in its capital city Springfield, which lies in Sangamon County. In 1995, Sangamon State University was incorporated into the University of Illinois family and renamed the University of Illinois at Springfield (UIS).

Since then, these three campuses—Urbana-Champaign, Chicago, and Springfield—have comprised the University of Illinois System, whose website is uillinois.edu, not to be confused with Urbana-Champaign’s illinois.edu, and whose legal name is the University of Illinois, not to be confused with the university formerly known as the University of Illinois.

Error in the system

The University of Illinois System was a well-oiled machine until 2009, when Springfield went rogue and axed the “at” in their name, becoming University of Illinois Springfield. The inconsistency remained for 11 years, with the other universities still “at Chicago” and “at Urbana-Champaign.”

Then something in 2020 gave Chicago and Urbana-Champaign some time for self-reflection. That fall, they finally followed Springfield’s lead, quietly removing the “at” and rebranding to the University of Illinois Chicago and the University of Illinois Urbana-Champaign. But not everyone got the memo.

Excerpt from the University of Illinois System style guide

It wasn’t until spring 2021 that the university’s Wikipedia article was moved to remove the “at,” as a result of the same talk page discussion that restored the hyphen. Even still, the press isn’t on the same page about the name of the University of Illinois Urbana-Champaign. You’ll still find the “at” in The New York Times, the Chicago Tribune, and even style guide goliath AP. If you even ask a current student at the university, chances are they won’t know the “at” was removed, since the university never formally announced it.

Well, consider this your announcement. There is no “at” in the University of Illinois Urbana-Champaign.

What should I call it?

In casual conversation, reciting the 14-syllable University of Illinois Urbana-Champaign every time you refer to the school will get tiring. But lucky us, the university officially recognizes four nicknames for use on “second and subsequent references.” Let’s break them down:

University of Illinois

This former name of the university still sticks around as an abbreviation of sorts, but the university has mixed feelings about it. Since it’s also the official name of the University of Illinois System, the Office of Public Affairs at the Urbana-Champaign campus declared as of 2018, “Do not use the name ‘University of Illinois’ to refer to this campus.”

But people do anyway. In fact, if you search “University of Illinois” on Wikipedia, it redirects to the Urbana-Champaign campus, not the system.

You might be thinking, aren’t there three Universities of Illinois? What do the Chicago and Springfield campuses think of this? Well, the Urbana-Champaign campus is the O.G., the flagship, and the system’s largest campus to this day, with about 56,000 students compared to UIC’s 34,000 and UIS’s 4,000. As an anonymous redditor posted last year, “nobody on this planet refers to UIC or UIS as ‘The University of Illinois,’” so if you trust that comment’s 50-something upvotes, I don’t think anybody’s feelings are being hurt. But “University of Illinois” is still kind of a mouthful.

U of I

This is probably the most common way to refer to the school if you’re in Illinois, talking to other people from Illinois. In the Chicago suburbs, where I’m from, it’s what everyone calls the school. It’s also an officially sanctioned shorthand for campus tour guides to use, and the Office of Public Affairs permits it “for in-state and alumni audiences.”

The mammoth statue at the university’s Natural History Building. I just think he’s neat.

Only problem is, if you say “U of I” anywhere outside of Illinois, you’ll be met with confused looks. As of now, Wikipedia lists seven different universities on the “U of I” disambiguation page, including neighboring state university and fellow Big Ten member University of Iowa. Not great! But luckily, there’s another option, and it’s the same number of letters.

UIUC

Every good school has an acronym. Chicago has UIC, Springfield has UIS, and Urbana-Champaign has UIUC.

The acronym UIUC has been in use to some degree since the ’70s, especially by professors and nerds, and especially on the internet. Registered in 1985, uiuc.edu was one of the oldest .edu domains, serving as the university’s website and email domain until it moved to illinois.edu in a 2008 rebrand. UIUC is also the name of the university’s subreddit, which was at one point the largest university subreddit in the country (curse you r/berkeley).

But the acronym isn’t without its downsides. The university doesn’t really use it in any official marketing material, especially since the 2008 rebrand. The acronym is better suited for text than for speech, with the muddle of “you-eye-you-see” often indistinguishable from UIC when spoken aloud. Relatively new in the lifespan of the university, the acronym also leaves a bit of a generational gap. My grandparents, who attended the university in the 1950s, never called it UIUC, and my mom, who has lived in Illinois all her life, had never heard UIUC until I was applying there in high school.

At the end of the day, kids these days still call it UIUC, and if you say it to someone who has been in school in the past decade, they’ll probably know what you’re talking about. And it’s about time someone puts it in a crossword.

Appearances (or lack thereof) of UIUC in major crossword outlets, per Crossword Tracker

Illinois

The university has leaned into this nickname since 2008, and for good reason. It’s iconic, it works in both text and speech, and it’s unambiguous (assuming you’re not talking about UIC, UIS, Illinois State, Illinois Tech, or Illinois College). As the flagship state university of Illinois, it’s metonymous with the state itself, like how Michigan and Minnesota also refer to their respective flagship schools.

The nickname “Illinois” will be especially recognizable to anyone who’s ever looked at the Big Ten standings or a March Madness bracket, since ESPN has no time to rattle off the university’s full name. It’s all over T-shirts and hoodies, it’s in every student’s email address, and it’s plastered at the top of the university’s website.

The Alma Mater statue, as pictured on illinois.edu. Not to be confused with the university’s alma mater song “Hail to the Orange,” which aptly ends “Victory, Illinois, Varsity.”

This school has gone through a lot of names in its 156 years, from Illinois Industrial University to the University of Illinois to the University of Illinois at Urbana-Champaign to the University of Illinois Urbana-Champaign. But today, if someone asks me where I go to school, my answer will be simple, and it’s been in the name all along: Illinois.

For more adjacent to the University of Illinois Urbana-Champaign, check out these Wikipedia articles I recently wrote on Pinto Bean and Unofficial!

***

Sources and further reading

• A Brief History of the University of Illinois, University of Illinois Archives (1970)
• History of the name of the University of Illinois at Urbana-Champaign, University of Illinois Archives (2011)
• Urbana-Champaign Campus Designation, Campus Administrative Manual (2018)
• Our name, Office of Strategic Marketing and Branding
• History of the Universities, University of Illinois System
• Writing Style Guide, University of Illinois System
• History, University of Illinois Chicago
• The power of a name, University of Illinois College of Liberal Arts & Sciences (2021)

“Hmm, I do have a bunch of time to kill,” I said, being in my last winter break of college.

A week later, New Year Zone was born. But to tell the full story, we have to go back.

My dad Larry says:

Back in the 1980s, I came up with the fun idea to compile a list of locations worldwide that celebrated the New Year at each hour of the day on December 31. I kept the handwritten list in a safe place and pulled it out every New Year’s Eve for years. (Actually, I kept the list inside a Styrofoam skimmer hat that I’m pretty sure I got from Constructive Playthings (US Toy Company) when I ran a Purim carnival together with my friend Dave sometime in the early ’80s. Also, I hand-colored a half-inch dowel rod with festive stripes, and each year on New Year’s Eve, I’d happily wear the skimmer hat and carry the dowel rod (as though I was some sort of circus barker), celebrating the New Year each hour according to my list.)

Flash forward to December 31, 2021, when I mentioned to Adam that I wanted to create an app or website that would alert people each hour on the hour where it was a New Year all day on New Year’s Eve. Seed planted! A year later, Adam took the leading oar and made it happen. Thank you Adam. And welcome to NEW YEAR ZONE™!

Thanks Larry, now back to Adam:

That Larry guy, what a character! Anyway, New Year Zone is a website that counts down to the New Year in every time zone, so that you can celebrate every hour like my dad did in the ’80s. It was a joint project between the two of us: think of me as the lead engineer and designer, and my dad as the product manager. The site’s design takes inspiration from my dad’s striped dowel rod, but unlike his dowel rod, it changes colors for each new time zone!

I developed New Year Zone in TypeScript and React, with SCSS for styling and Framer Motion for animation. The project is built with Vite and hosted with Cloudflare Pages (which I gotta thank my friend Christian for helping me configure).

Building the site presented tons of fun little technical challenges, like how to synchronize 38 clocks, how to fit a timer perfectly to the width of the screen (it’s harder than it should be), or how to implement a Wordlesque sharing functionality. The countdowns use the widely loved JavaScript Date API, syncing with your device’s clock to accurately determine the current time and your local time zone.

About time

As it turns out, when you make a website about time zones, you learn a lot about time zones along the way. Here are some of my favorite time zone facts:

• There are 38 time zones. I feel like this number is never talked about like how there are 50 US states or 118 elements. But the secret’s out, there are 38, count ‘em!
• The latest time zone, UTC+14, is 26 hours later than the earliest one, UTC−12. If you do the math, that’s more than a day! That means you could be later in the day on Sunday than someone else is on Saturday, at the same time.
• I knew there were some time zones offset by 30 minute intervals, but did you know there are a few offset by 45 minutes? New Zealand’s Chatham Islands use UTC+13:45 time, Nepal uses UTC+5:45, and wait ‘til you hear about the next one.
• My new favorite time zone is UTC+8:45, known in Australia as Central Western Time. It applies to a few towns along a stretch of highway connecting South Australia and Western Australia, with a total population of about 200 people. Legend has it, they couldn’t decide between South Australia and Western Australia’s time zones, so they just created their own. The Australian government hates this and doesn’t officially recognize Central Western Time, but Australia’s wild west doesn’t care. Road signs along the highway will kindly remind you to advance your clocks by 45 minutes.
  
  

from Wikimedia Commons

Get in the zone!

Now it’s your turn to be the New Year circus barker! Grab the nearest styrofoam hat and striped dowel rod, and tell your friends about New Year Zone. And wherever you are in the world, Happy New Year!

New Year Zone

When I unboxed the AirPods on February 24, 2020, in my Illinois dorm room, the first thing I listened to on them was Steely Dan’s album Aja, because of course it was. I’m no audiophile, but these were good headphones, and I was about to listen to a lot more music on them.

I like making lists of things, and this seemed like as good a time as any to start making a list of the albums I’ve listened to.

Hey Siri, define “listen”

I was going to take this list seriously. These were the arbitrary rules I laid out for myself:

• I have to listen to each album on the AirPods Pro, just to put them all on even ground and ensure some benchmark of audio quality
• Each album on the list must be a full-length LP (no EPs)
• No dupes, each album can only be listed once
• I have to listen to the whole album, in order (see this rage comic)
• I don’t have to do it all in one sitting (I have a life, you know)

I would keep the list in Evernote at first, transitioning to Notion around the start of 2021.

The Moon System

I wanted some way to rate each album. I didn’t want there to be too much granularity, or else I’d spend less time listening and more time thinking “is this more of a 7.5 or a 7.6?”

So I devised a totally subjective, low-granularity, vibes-based rating system using moon phase emojis for some reason. Introducing the Moon System:

• 🌑 New Moon: Awful album. In practice, no album has gotten this rating because if it’s really that bad, I’m probably not gonna finish listening to it.
• 🌘 Crescent: Okay album. Nothing to write home about. At least I finished it.
• 🌗 Half Moon: Pretty good album. Mostly enjoyable, maybe a few weak spots.
• 🌖 Gibbous: Great album. Overall enjoyable, would listen to again.
• 🌕 Full Moon: Amazing album. All bangers, no skips.

I would assign every album on the list one of these moons immediately after listening. I could go back and amend previous moon ratings, but only if I listened to the album again.

By its very nature, the Moon System skews positive. The half moon is in the middle, and it’s still pretty good. And every album I rate is one that I voluntarily listened all the way through, so the scale is biased toward albums I like anyway.

Full Moon Albums

Two and a half years later, the Moon System is still going strong. I’ve gotten ridiculous mileage out of my AirPods (now nicknamed AdamPods in my phone). I’ve listened to over 950 albums on these badboys, on track to pass 1,000 by the end of the year. Of those, I’ve given 76 the coveted Full Moon.

Up until now, my album list has existed purely for my own record. Notion has proven great for keeping a giant list of albums, letting me sort and filter the list by artist, date, or moon rating. It’s perfect for getting a glance of which Beatles albums I like the most, or how many albums I listened to in October. But I’m not really doing anything with all this data.

It’s about time for that to change. I’m not releasing the entire list, because no one cares what albums I didn’t really like. But I do think there’s value in sharing my favorites. These are the ones I keep coming back to, the masterpieces, the S-tier, the all bangers, no skips, all bops, no flops, all killer, no filler:

Full Moon Albums

Take these as my recommendations, and let me know if you find something in there you enjoy! Just like my list in Notion, you can sort the Full Moon Albums in various orders and filter them by genre and vibes. After curating this list, it feels like a well-rounded portrait of my taste in music. Of course, my taste is just my opinion, but I think there’s something for everyone in there.

I made the site in TypeScript with React and SCSS, along with some Python preprocessing that uses the Spotify API to fetch the cover art and Spotify link for each album. I used Vite to build the project, which I highly recommend for TypeScript React apps. For the curious, all the source code is here.

As my album list barrels into quadruple digits, I plan on updating Full Moon Albums regularly. Discovering new music is one of my greatest joys, and I’m hoping Full Moon Albums can share some of that joy with the world!

Dec 25, 2022 update:

Today I logged album #1000, which was New York–London–Paris–Munich by M, one of my dad’s favorites that I thought was apropos for the milestone. I gave it a 🌖.

For the uninitiated, here’s how it works. Players take turns taking trickshots, and if one player makes it, the other player has to match that shot. If the other player misses, they gain a letter in the word H-O-R-S-E, starting with H. If you miss five shots that your opponent made and spell the whole word, you lose! It’s a timeless classic, enjoyed by everyone from middle schoolers to NBA All-Stars to Obama.

There’s nothing special about horses.^{[citation needed]} You could just as easily play Z-E-B-R-A or H-U-M-A-N, and the game would play out exactly the same. Players at home might be familiar with P-I-G, a game that’s identical to H-O-R-S-E, except you lose after three letters instead of five. This is perfect if you’re in a time crunch, or you otherwise lack the commitment to play for five whole letters.

But what if you’re a real power player? What if you have all the time in the world? What if you want to play H-O-R-S-E, but make it even longer?

What’s the longest animal name you can play H-O-R-S-E with?

The rules

You can’t play H-I-P-P-O, for example. If a player gains a P, how do you know if they missed their third or fourth shot? In H-O-R-S-E, you can describe a game’s state just by saying “Alice is at R, Bob is at S.” But in H-I-P-P-O, you’d have to say “Alice is at H-I-P, Bob is at H-I-P-P.” That’s way too much work, and it’ll get really tiring for even longer animal names.

So we have a rule: no repeated letters allowed. In other words, the animal’s name has to be an isogram, a word where every letter appears exactly once (alternatively known as a heterogram, but isogram wins because it’s one of those nice self-descriptive wordplay terms—isogram is itself an isogram).

That means our question boils down to: what’s the longest animal name that’s an isogram?

I posed this question to my friends while we were waiting for our pub trivia sheet to be graded, and we contemplated it for a solid 15 minutes. The longest one we thought of that night at Murphy’s Pub was the 10-letter ANGLERFISH (hat tip to my friend Aakash for that). That would make for one long game of H-O-R-S-E!

But we can do better. It’s surprisingly hard to think of isograms, let alone ones longer than 10 letters. That’s where computers come in.

The plan

It seems like no one has tried to solve this problem before, possibly because it bears no societal implications.

Isograms are rare, especially long ones. As words get longer, they contain more letters,^{[citation needed]} so there are fewer possible letters to add that aren’t already in the word somewhere. This means the probability that a randomly spelled word is an isogram decays roughly exponentially as its length increases. (Incidentally, this is just like the birthday problem, which asks about the probability of a random group of people having any shared birthdays. Except here, the people come from a planet with 26-day years.)

English words aren’t spelled with random letters, but they still more or less follow the same isogram distribution. If we look at a list of English words, we can see the steep falloff in isograms as word length increases. About 66% of five-letter words are isograms, versus about 5% of ten-letter words and 0.06% of fifteen-letter words—the only two being DERMATOGLYPHICS and UNCOPYRIGHTABLE—and there are none any longer:

Of course, we’re not looking for any old isogram, we want animal isograms! Rather than an English dictionary, we need a list of animal names. In particular, we want a massive list of animal names. More animals means more chances for rare long isograms to appear.

Once we have a list, finding its longest isogram is actually the easy part. We can just use Wordlisted, a webapp I made that lets you upload any wordlist, search it for words with various features (one of which is isograms, conveniently), and sort the results by length. Thanks, past me!

So here’s the plan: acquire a comprehensive list of animal names, and throw it into Wordlisted to find its longest isogram. Easy, right?

But uh, where do you get a comprehensive list of animal names?

Take 1: A-Z Animals

If you google “list of animals,” one of the top hits is the aptly named website A-Z Animals. It’s a big honkin’ list of animals ranging from aardvark to zuchon, with fun facts about each one. This seems like a good starting place.

So I whipped up a Python script to scrape the A-Z Animals list using Beautiful Soup, and before I knew it I had a txt file of 2,093 animal names. Maybe not comprehensive, but pretty good. I tossed it into Wordlisted, and out popped a 12-letter isogram, the new front runner for longest H-O-R-S-E animal:

BREDL’S PYTHON

from A-Z Animals

How fitting! Python in, python out. Bredl’s python is a python species native to Australia, named after Australian snake guy Josef Bredl. According to A-Z Animals, “these snakes love to climb trees, and young snakes often hide high in the branches.”

That’s progress! But we can do better.

Take 2: WordNet

My next order of business was to consult wordplay programming maven Alex Boisvert of Crossword Nexus fame. I asked him the question at hand: what’s the best way to scrape a massive list of animal names? Spitballing, I suggested I could try WordNet, an enormous database of lexical items tied together with synonyms and other relations.

As it turned out, one of WordNet’s relations is hyponyms, words that describe a subset of other words—for example, square is a hyponym of rectangle, and waffle is a hyponym of food. That means finding a list of animals was as simple as finding every word in WordNet that’s a hyponym of animal. Naturally, Alex had a chunk of Python code sitting around that did exactly that: find every word in WordNet that’s a hyponym of some other word.

After a few minutes of figuring out how to download WordNet (it’s pretty easy with NLTK), a few seconds of running Alex’s code, and a few minutes of cleaning up the resulting data, I now had a txt file of 7,262 animals. A marked improvement over A-Z Animals!

With more animals came more isograms, and with more isograms came a new longest isogram. Introducing an animal you can play a 13-letter game of H-O-R-S-E with:

JUNCO HYEMALIS

from Wikimedia Commons

Junco hyemalis is the scientific name of the dark-eyed junco, a species of sparrow native to North America. That’s right, WordNet has both common names and scientific names. That feels fine to me, since this is all in the name of science.

It just so happens that Junco hyemalis contains exactly one of each vowel, making it supervocalic (another self-descriptive wordplay term). It even has a Y, making it euryvocalic (another!). In fact, you’ll see that long isograms tend to be super- or euryvocalic. As words get longer, they need more vowels, and since isograms can’t repeat old vowels, they’ll eventually need to use all five or six.

Unlike WordNet, A-Z Animals doesn’t list scientific names like Junco hyemalis, but it does list the dark-eyed junco! Their fun fact about our favorite euryvocalic isogram bird is: “they are called snowbirds because many subspecies reappear in the winter.”

Lovely! But we can do better.

Take 3: Wikidata

I figured there had to be some way to scrape every animal from either Wikipedia or its sister database Wikidata.

So I reached out to Lucas Werkmeister, a Wikidata developer who I found through some shenanigans he did with depths of wikipedia. I asked him my question, and soon enough he sent me this query written in SPARQL (pronounced “sparkle”) that scours Wikidata for every species in the animal kingdom along with its taxon name (Wikidata’s term for scientific name). I tried running his query in the Wikidata Query Service, but the request timed out. This was both a problem, since I couldn’t get the results, and a good sign, since that meant there were a ton of results.

Thankfully, Lucas pointed me toward a Mastodon post that addressed this very issue. One reply to this post led me to QLever (pronounced “clever”), an open-source SPARQL engine developed at the University of Freiburg in Germany. Not only did QLever run Lucas’s Wikidata query without timing out, it ran it in like 2 seconds.

After downloading the data from QLever and cleaning it up in Python, I suddenly had a txt file of over 1,700,000 animal names, ranging from the absurdly-named beetle Aaaaba nodosus to the sponge-dwelling cnidarian Zyzzyzus warreni. Take that, A-Z Animals! Like WordNet, Wikidata stores both common names and scientific names, but unlike WordNet, Wikidata has several orders of magnitude more animals.

Plugging a list of 1,700,000 animals into Wordlisted was a real moment of truth, both as a search for isograms and as a stress test for Wordlisted. But this was a success on all counts, yielding a result in a league of its own. Against all odds, here’s a 16-letter isogram animal:

HABRONYX FULVIPES

This isn’t even Habronyx fulvipes, it’s a close relative in the Habronyx genus (from iNaturalist). As far as I could tell, there are no images of Habronyx fulvipes on the internet. I would love to know what this little guy really looks like!

Habronyx fulvipes is a species of wasp first described in 1965 by Henry Keith Townes, Setsuya Momoi, and Marjorie Townes. It has no Wikipedia page in English, but it does have one in Dutch and a few other languages. It also has no A-Z Animals page, which means I can’t tell you their fun fact, so instead I’ll come up with my own. My fun fact is, “its species name fulvipes is Latin for yellow legs, which is a reference to the wasp’s yellow legs.”

More importantly, Habronyx fulvipes is an ultra-rare 16-letter isogram (that also happens to be euryvocalic), longer than any isogram in the English dictionary and more than three times the length of H-O-R-S-E. For all intents and purposes, this is the answer to our question. But here are some honorable mentions:

• Longest one-word isogram animal: PAMBDELURION (12 letters), an extinct species of arthropod, which is also supervocalic and sounds like a sci-fi villain
• Longest common name isogram animal: BROWN PALM CIVET (14 letters), a species of civet, which can also be pluralized to the isogram BROWN PALM CIVETS (15 letters)
• Longest isogram animal with an English Wikipedia page: a tie between AMPHONYX LUCIFER (15 letters), a euryvocalic species of moth, and GLYPHODES UMBRIA (15 letters), a euryvocalic species of moth
• Shortest isogram animal: probably OX

Hopefully that should give you plenty of options. A little Wikidata query will go a long way!

Moral of the story

Society has progressed past the need for H-O-R-S-E. Soon enough, all the cool kids will be on the court, sinking trickshot after trickshot, playing H-A-B-R-O-N-Y-X-F-U-L-V-I-P-E-S.

Naturally, your first guess is 50, since you’re trying to cut the possibilities perfectly in half. I tell you it’s higher, so you guess 75. I tell you it’s lower. You keep splitting the possibilities in half, until eventually you’ve narrowed it down to one number (it was 59, good job). With this strategy, it turns out you can figure out any number from 1 to 100 in at most seven guesses. Or any number from 1 to a million in at most twenty.

In computer science, we’ve got a name for this narrowing-down procedure: binary search. As long as the possibilities are sorted in some way (like numbers in numerical order), we can home in on one at lightning speed just by repeatedly cutting the possibilities in half.

But guessing numbers isn’t very interesting. What if we could generalize binary search to more than just numbers—what if we could binary search through all of the things?

As it turns out, you can. It’s a little game called Twenty Questions.

Twenty Questions is a weird game

We’ve all played it. At the core of Twenty Questions, you have an answerer and one or more guessers. The answerer thinks of a thing, and the guessers have to deduce that thing purely by asking the answerer yes–no questions. Traditionally, the guessers have a whopping twenty questions to guess the thing, otherwise they lose.

As a game, this doesn’t really seem fair. If the answerer is motivated to win, they can just think of a thing so obscure that the guessers couldn’t possibly guess it in twenty questions. And that’s super easy to do, since twenty questions isn’t enough to guess almost anything!

To understand why, we have to do some math. Asking a yes–no question is just like asking if a number is higher or lower: it gives you a bit of information that cuts the possibilities into two groups. That means two yes–no questions create four groups, three questions create eight groups, and in general, n yes–no questions create 2ⁿ groups. In particular, twenty questions is enough to distinguish 2²⁰, or 1,048,576 types of things—this is exactly why you can deduce any number from 1 to a million in twenty guesses.

But in Twenty Questions, the answerer doesn’t have to think of a number from 1 to a million, they can think of anything. And, well, there are way more than 1,048,576 things. For example, numbers are things, and we can conceive of way more than a million numbers (like negatives, or fractions, or 1,048,577), so twenty questions isn’t even enough for numbers. But chances are the answerer isn’t thinking of a number. What about every possible word, or location, or event, or type of pasta? It doesn’t take long to realize that the number of conceivable things is infinite. As John Green (or Georg Cantor) taught us, some infinities are bigger than others—and the number of things is a really big infinity.

You might be thinking, wait, if there are infinitely many things to narrow down, couldn’t the game take infinitely long? Theoretically, maybe, but in practice, no. This is kind of a paradox. Even though we can conceive of infinitely many things, any particular thing will be guessable in a finite number of questions. After all, the answerer can only reach so far into the infinite depths of the universe before they decide on a thing, and any particular thing will be expressable in a finite number of words. Now it might not take twenty questions—in fact, it almost always won’t—but the game will end eventually.

How would I know? Throughout my life, I’ve played a lot of Twenty Questions, whether it was with my cabinmates at overnight camp, with my friends in high school and college, or with random people on Sporcle’s Twenty Questions forum. Even with infinite questions, the games always find a way to end—everyone still calls it Twenty Questions, though, for old time’s sake. The way I see it, playing with no question cap distills the game to its purest form. Besides, it’s far more satisfying for everyone if the guessers can reach that “aha!” moment, rather than having the game be artificially cut short after a measly twenty questions.

But wait a second, if there’s no question cap, how is this even a game? There isn’t really a winner or a loser, unless the guessers give up, in which case the answerer is disappointed and everyone loses.

That’s because Twenty Questions is a cooperative, asymmetric game. It’s cooperative because everyone is ultimately working toward a common goal: deducing the answer. And it’s asymmetric because different players have different amounts of information: the answerer knows the thing, but the guessers don’t, and they gain more information about the thing as they ask more questions. Information asymmetry is unstable and makes us uncomfortable, but if the guessers figure out the thing, the asymmetry is eliminated and everyone’s happy. So how can they get there in as few questions as possible?

The questions

This goes back to binary search. Remember how if I’m thinking of a number from 1 to 100, you wanted to guess 50 to split the options perfectly in half? If you had instead guessed 90, the majority of the answers are lower, so most of the time I’ll say “lower” and you’ll still have 89 numbers to sift through. But by guessing 50, you minimize that majority, which ends up minimizing the expected number of remaining options. Splitting the options perfectly in half is the optimal strategy, ensuring that every guess gives you as much information as possible.

The same logic applies to Twenty Questions. In a truly optimal strategy, each question would split the remaining things perfectly in half. Realistically, this is pretty infeasible, unless you have a perfect mental taxonomy of everything in existence. But you can still use this as a heuristic to guide your question-choosing strategy.

For one, don’t start guessing individual things (like asking “is it a toothbrush?”) until you’ve already narrowed things down significantly. If the thing is right, then it’s your lucky day, but if not, it makes essentially no progress and leaves you in exactly the same place as you were before. It’s like playing the 1 to 100 game and guessing 100 first.

With that in mind, we can start thinking about what questions are effective in a game of Twenty Questions. I’ll start with the first question I ask in every single game, a question so important that many other questions make no sense without answering it first, a question so ubiquitous that my friends and I started abbreviating it simply as “is it T?”:

“Is it tangible?”

This question crucially distinguishes two types of things: ones that exist in a physical form (like objects, places, and living things), and ones that don’t (like ideas, actions, and events). This is about as good of a 50/50 split as it gets—each subgroup is its own little infinity.

So now you know whether it’s tangible. Great! Now what? It’s time to narrow things down.

Tangible things

These are often easier to figure out. We have a strong intuition for how to categorize and compare physical objects, so we can more closely approximate binary search with them (remember, binary search only works on sorted data). But there are a lot of tangible things—infinitely many! Here are some questions that roughly halve that infinity into two smaller infinities:

“Is it alive?”

People like to think of animals, plants, and especially other people, and luckily scientists have gotten really good at classifying these. If it’s living, you can start deducing the thing taxonomically (“Is it an animal? Is it a mammal? Is it a member of the family Mustelidae?”). And if not, you’ve just cut out a ton of possibilities.

“Is it countable?”

This is a little more subtle. It basically asks if the answer is more of an uncountable “stuff” (like sand or grape juice) or a countable “thing” (like a bench or a fanny pack). Lots of questions only make sense for stuffs or for things, so this is a helpful distinction moving forward.

“Is there more than one of it?”

Hey, it’s a question that only makes sense for things, not stuffs! If it’s a yes, you can start to ask questions about how many there are or where they’re usually found (inside, outside, in the bathroom, on the wall, etc.). But if it’s a no, you can start narrowing down on the thing’s location, which is usually a straightforward path to the endgame.

“Is it bigger than a breadbox?”

This question has been known to prompt confusions like “well, it’s bigger in one axis, but smaller in another” or “wait, what’s a breadbox?” But this is an unironically great question. In practice, about half of the physical things we think of are bigger than a breadbox, so this question is useful to gauge whether we’re dealing with more of a fridge-sized thing or a baseball-sized thing. Either way, it’s such a classic question that it’s irresistible to ask.

“Is it made of a common material?”

From here, if it’s a yes, you can go on to deduce the actual material, which is good to know. This is one of many “meta-questions” that I’ve found surprisingly useful—questions that don’t carry much information themselves, but can help guide the guesser’s train of thought and open the door for more informative questions. Other questions of this kin include “is it usually a certain color?,” “is it typically used by a certain type of person?,” and even questions like “would it be helpful to ask about X?”

Intangible things

Intangible things can be harder to conceptualize and categorize, which often makes them trickier to figure out. But don’t panic! These can make for very interesting games, and they’re doable as long as the guessers have a decent plan of attack.

Here’s one bad question people always seem to be tempted to ask: “Is it an idea?” Really, basically everything is an idea, so this doesn’t actually give you any information. Instead, I recommend trying some of these questions:

“Can you observe it with any of the other five senses?”

Sure, you can’t touch it. But can you see it, hear it, smell it, or taste it? Okay, probably not smell or taste, unless the answerer is thinking of “umami” or something. But plenty of intangible things are visible or audible (like the color purple, or the Nike Swoosh, or “Mambo No. 5”), so this is useful information.

“Is it something that happens?”

A lot of intangible things are events, phenomena, or actions: things that happen! If this is the case, you can go on to figure out where, when, and other conditions under which it happens.

“Is it fictional?”

Fictional characters and things are a surprisingly tough type of answer to figure out, since it’s easy to go down a rabbit hole of intangibility before realizing it’s just a tangible thing in an intangible universe. It’s not a bad idea to ask this early on just to crack open this case.

“Would you learn about it in a particular class?”

This is probably my favorite meta-question for intangible things, because it helps you deduce so many different things. If the answer here is yes, you can go on to deduce the class, which can be a helpful frame of reference. This is huge for mathematical objects, scientific phenomena, historical events, and lots of other categories of things.

“Does it involve a particular tangible thing?”

Many intangible things can’t exist without something tangible. For example, tennis isn’t tangible, but it involves tennis balls and tennis rackets. A high five isn’t tangible, but it involves human hands. In a lot of cases, this question can reduce a hard intangible Twenty Questions game into a much easier tangible game. Once you figure out that tangible thing, all that’s left is to deduce how exactly it’s involved. Does it require more than one of them? Does the thing move? The world is your oyster.

The answers

Now we’ve talked a lot about the guessers’ strategy. But that’s just one side of the story! There’s also a surprising amount of strategy involved in being the answerer.

In many ways, the answerer is the leader of the Twenty Questions game. Like the creator of an escape room, or the dungeon master in Dungeons & Dragons, their ultimate goal is to make the game fair and fun for the players. The answerer has two main responsibilities: answering the questions, and coming up with a thing in the first place.

When it comes to answering questions, you might think the answerer’s role is pretty clear-cut: just say yes or no. But in practice, many yes–no questions are more accurately and fairly answered with more nuance than that. In cases where “yes” or “no” don’t tell the full story, it’s in everyone’s best interest to give answers like “it depends,” “usually,” “irrelevant,” or “I can’t answer that because your question entails a false assumption about the answer.”

Twenty Questions is not a word game

I have to get this off my chest. Look, I love word games as much as anyone else. But at its core, Twenty Questions is a thing game, not a word game, and there are a few problems with thinking of it as such.

First off, if the answerer is just thinking of a word, then the guessers can just deduce the answer by rote binary search, asking “is the first letter in the first half of the alphabet?” and “is the first letter between H and M?” and so on. Now if this is your definition of fun, then have at it. But to me, these kinds of questions collapse the game into a triviality, eliminating any notion of strategy or creativity. If the guessers get so frustrated that they resort to these questions, I try not to answer them and instead steer them in the right direction.

But in most cases, it doesn’t even make sense to reduce the thing to the word that represents it. What we actually care about is the referent, the thing the word actually refers to, not the word itself. This is because one word can often have multiple possible referents, and the game falls apart unless the thing is just one of them. For instance, one of my friends once chose the thing “mark” (since my buddy Mark was right there). The thing is, “mark” can mean a lot of things—it has dozens of definitions listed on Merriam-Webster as a noun alone—and my friend wasn’t thinking of one in particular. This meant pretty much all his answers were wishy-washy and unclear, and it didn’t take long for us guessers to rage-quit.

Sometimes the distinction between meanings is more subtle, but equally game-ruining. Let’s say the answerer is thinking of McDonald’s. Now, is it tangible? The correct answer is: it depends. They might be thinking of a physical McDonald’s restaurant building, which is tangible, or they might be thinking of the corporate entity McDonald’s, which is intangible. It’s subtle, but the distinction is there. This is what linguists call polysemy, when one word has multiple meanings that are closely related, but distinct.

So, when you’re the answerer, make sure to think of a thing, not just a word. A neat side effect of this is that the guessers don’t have to name the thing verbatim, as long as it refers to the same thing. If the answerer thinks of a roundabout, the game still ends if someone guesses a “rotary” or a “traffic circle.”

Alright, the only exception here is if the answerer’s thing is literally a word, in which case the best way to deduce it is by first figuring out that it’s a word, then binary searching the alphabet. But I’ve tried this before and I can’t say I recommend it. You can imagine my friends’ excitement when they found out my thing was “the word because.”

Here’s the thing

Finally, this brings us to the strategy behind selecting a thing. There are a few factors to consider here.

If the answerer chooses a ludicrously obscure thing, the guessers will never figure it out, which is no fun. But if the thing is so straightforward that the guessers will quickly get it, there’s less of an “aha!” moment, which makes the game less satisfying. That means selecting a thing is a balancing act: think of something that’s a little out-there, but not too out-there.

In my experience, the most interesting things for an answerer to choose are ones that are well-known but difficult to categorize. Something like a person, food, animal, or location is a perfectly cromulent thing, but once the guessers figure out its category, deducing the thing suddenly becomes straightforward. But if the thing isn’t in a clear-cut category, it takes a little more mental gymnastics to get there.

Here’s an assortment of things I’ve found that strike that balance—familiar, but challenging to deduce—and make for a certifiably fun game of Twenty Questions:

• Air guitar
• Ball pit
• Confetti
• Five-second rule
• Foam finger
• Fourth wall
• Googly eyes
• House of cards
• Lint
• Message in a bottle
• Moving walkway
• Packing peanut
• Peek-a-boo
• Pegman
• Piñata
• Pizza table
• Porta-potty
• Roy G. Biv
• Speed bump
• Standing ovation
• Tube man
• Velcro

Try this at home, kids!

Now it’s your turn! Go play Twenty Questions with your friends (but with infinite questions, of course), and give some of the above things a try or come up with your own. You’ll quickly be reminded how elegant the game is: few rules, zero equipment, and truly infinite replay value. It feels inevitable—if you restarted society from scratch, someone somewhere would eventually reinvent Twenty Questions. It’s what I like to call a “nothing game,” in that you need absolutely nothing to play it, just some friends and a little bit of patience.

I might go into Twenty Questions variants and other “nothing games” in future posts. But while you’re waiting, there’s no better way to pass the time than a good old fashioned game of Twenty Questions.