Although no one explicitly teaches it, if you’re a crossword puzzle enthusiast, chances are you have developed a fluent understanding of the grammar of crosswords. Crossword solvers are aware that nouns clue nouns, verbs clue verbs, and so on. They also intuitively grasp that answers must be interchangeable with their clues in a sentence, even for specific categories that don’t have a designated name. These unwritten rules can be deceptively complex. For example, the word GALORE can be clued by “aplenty,” but not by “many.” This is because, although both are adjectives, only galore and aplenty come after the noun they modify (while most other English adjectives come before). By solving enough puzzles, our brains can learn that multi-word crossword answers must form what linguists refer to as a syntactic constituent— a group of words that function together as a complete unit, like “safe and reliable,” but not “safe and.”
The rules of crosswords are part of a larger set of conventions shared among solvers, and they are closely connected to the grammar of language in general. Just as toddlers develop a deep understanding of different word classes without being explicitly taught about nouns or verbs, crossword solvers develop strong intuitions about what entries are possible and how they can be clues. These intuitions help them recognize what makes a good answer, such as OPRAH (“Founder of Harpo Productions” in a 2019 New York Times puzzle), WHO GOES THERE (“Sentry’s query” from 2018), or BANANA SPLIT (“Dessert served in a boat” in a 2022 entry).
However, the true mark of crossword solvers’ effortless familiarity with the rules lies in their ability to identify what makes a bad answer, like SUPERB PAN (“Amazing thing to fry bacon in”) or ORDER A RYE (“What the whiskey lover would do at the bar”). These subpar entries come from the work of Trip Payne, a crossword constructor and speed solver known for his absurdist “Cuckoo Crosswords.” Payne’s puzzles intentionally feature comically bizarre entries that solvers agree have no place in a typical puzzle. For instance, one puzzle from 2021 had the clue “Vanity on the set of ‘Uncut Gems,'” with the answer being ADAM SANDLER’S EGO.
While entries like SAFE AND go against basic English language principles, the cuckoo entries in Cuckoo Crosswords violate a more subtle, but equally fundamental, crossword rule. In both cases, crossword solvers have learned through experience what makes a given entry acceptable or cuckoo, as well as what distinguishes truly exceptional entries. Although these rules are specific to crosswords, they rely on broader linguistic intuitions— the acquired knowledge about language that resides in our brains, even if we’ve never consciously pondered over it.
Cuckoo answers like ADAM SANDLER’S EGO are grammatically valid English phrases that can easily replace their clues in a sentence, much like more acceptable entries like PANDORA’S BOX or ACHILLES’ HEEL. However, for reasons that may be difficult to articulate, they still lack the satisfaction solvers seek. Crossword constructors have coined the term “green-paint entries” to describe answers like these— entries such as ADAM SANDLER’S EGO, SUPERB PAN, and ORDER A RYE are all examples of green-paint entries, just like GREEN PAINT itself.
Some crossword experts argue that solvers find green-paint entries bothersome because they are not commonly used in everyday language. However, encountering phrases like “order a rye” (“Hi there, I’d like to order a rye”) in daily life wouldn’t raise an eyebrow— in fact, depending on one’s interests, they are more likely to encounter such phrases than perfectly acceptable entries like APSE. The real reason ORDER A RYE is frowned upon in mainstream crossword society has to do with a linguistic feature called “compositionality.” Compositionality refers to the ability of language to combine smaller units of meaning into larger ones with predictable meanings. It is what allows us to comprehend multi-word phrases, such as “green paint” referring to paint that is green, or even completely new sentences like “Lady Gaga splattered the crossword grid with green paint.”
Compositionality is a fundamental aspect of human language, enabling us to express an infinite range of ideas using a finite number of words. However, for crossword solvers, purely compositional phrases often fall short. Answers like GREEN PAINT are unsatisfying because they offer little beyond the literal meaning derived from combining the words. Conversely, exceptional multi-word answers somehow surpass the sum of their parts. For instance, compare GREEN PAINT with GREEN DAY (clued in a 1996 New York Times puzzle as “Band with the Grammy-winning album ‘Dookie'”)— GREEN DAY does not refer to a green day in any way. Linguists refer to phrases like this as “non-compositional” since the meaning of the whole phrase cannot be deduced solely by combining the meanings of the individual words.
The concept of compositionality in crosswords is not black-and-white. Phrases can fall anywhere along the spectrum from fully compositional to entirely non-compositional, with various degrees in between. Consider GREEN TEA (“Sushi bar cupful” as clued in a 2003 New York Times puzzle). It is indeed tea, and it is somewhat green. However, knowing these facts alone doesn’t encompass everything one should know about green tea. It also carries a specific taste, history, and set of connotations. Adding green food coloring to black tea may make it tea that is green, but it doesn’t make it green tea.
The same logic applies to single words in crosswords. Fully compositional answers like REBROIL (presumably meaning “to broil again”) are more likely to irk solvers compared to words like RETURN. While both words are composed of smaller elements (re and turn), the meaning of return is not solely determined by the meanings of its components. Returning is not simply turning again.
To truly excel in a crossword puzzle, an answer should evoke a particular time, place, or atmosphere, reminiscent of Proust’s madeleine. That’s why purely compositional answers often fall flat— if a word or phrase feels made up on the spot, it lacks the ability to do so. Words like REBROIL or GREEN PAINT don’t evoke any specific associations because they lack their own distinct identity. On the other hand, a favorite dessert like MOLTEN CHOCOLATE CAKE, or an artist like TINA TURNER, or a technology like MACBOOK PRO can transport solvers to a world of prior experiences. When encountering these words and phrases, we remember their real-life context and even their emotional impact.
The sense of place adds an extra layer of fulfillment to phrases that may initially appear devoid of any meaning or associations beyond their constituent words. Take the entry SO RANDOM from a 2022 New York Times puzzle by Kameron Austin Collins. On its own, it roughly means “especially disordered.” However, many solvers recognize that the phrase is deeply rooted in a specific cultural moment. SO RANDOM conjures an image of a millennial, perhaps ironically or self-mockingly describing their own behavior, or even speaking with the voice of a character from Clueless. These assumptions are further supported by the clue: “Like… all over the place.” In contrast, an answer like ESPECIALLY DISORDERED would not tap into any cultural context.
In recent years, crossword constructors and editors have expanded the cultural context from which crossword answers are drawn. Today’s most beloved crosswords feature fewer obscure European rivers and more references to celebrities, allusions, and phrases from all walks of life. As Natan Last, a puzzle constructor for The New Yorker, puts it, having diverse voices as curators allows the world to be reflected in the grid. Modern curatorial voices include Juliana Pache, whose Black Crossword ventures beyond the traditional clue for MENTO, offering “Jamaican folk music that later influenced ska and reggae.” There are also constructors like Nate Cardin and his colleagues, who create Queer Qrosswords with an emphasis on LGBTQ themes. For example, a puzzle by Claire Rimkus and Andrew Kingsley in 2019 centered around the answer AUTOSTRADDLE, the name of a queer feminist online magazine.
Crosswords provide valuable insights into the intricate mental processes involved in combining words into phrases and organizing letters into words. Unlike most written language experiences, crossword answers lack spaces and are written as single entries.
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