The Wit’s Guide to Crosswords

Or, crucial cruciverbalism

Why Lizzie Was Late With The Lunch, a postcard from the “Cross-word Craze” series, ca. 1925

Crossword puzzles won across, won down, and won fair and square. When the checkered word games first became popular in the 1920s, the New York Times excoriated them as “a primitive form of mental exercise” and a “new utilization of leisure by those for whom it would otherwise be empty and tedious.” A century later, people spend more time doing puzzles on Times apps than reading the news. “The New York Times is now a gaming company,” they say, so crosswords saved journalism! (With an assist from the Wordle, but what are the odds that will survive another 100 years? SMALL. Phew!)

“She looked at me like someone who has just solved the crossword puzzle with a shrewd ‘Emu’ in the top right-hand corner.”
— P.G. Wodehouse

And this is why all newspaper headlines should be puns. People are there for the wordplay! The numbers prove it! Give them what they want! Martin Amis was a famous hater of puns, claiming “they offer disrespect to language, and all they manage to do is make words look stupid.” But he loved crosswords, noting in two of his books that the best take on James Joyce’s puzzling novel Finnegans Wake came via this clue:

Something wrong with Finnegan’s Wake? Perhaps too complicated.  (10 letters)

The answer, of course, is apostrophe, an anagram of “perhaps too” as set up by the signal word complicated, and wrong because the novel’s title lacks one. Obviously! Mart’s other fave:

Meaningful power of attorney. (11 letters)

Don’t all shout it at once, but the answer is significant, as in sign-if-I-can’t. Which reminds me that I like cryptic crosswords the way I like horror movies: Give me the twists and save me the trouble. To that end, I called on Zach Sherwin, creator and host of The Crossword Show and a friend of GWQ friend Myq Kaplan, to give me the goods, such as:

Wanders around an airport. (3 letters)

The answer being TSA. But I will here admit some of the goods are bads, in that I had to stare at them for longer than I’d like to admit, as in the cases of:

Diamond mine? (1,3,2 letters)
Chemical agent for climate change. (7 letters)

The first is a baseball reference for I GOT IT (It’s mine on the diamond), whereas the second features the same letters in the first two words as the last two plus the signal word “for,” hence ANAGRAM. Alright, here are some better ones, with credit to their creators:

Person dealing with a minor problem. (7 letters)
— Mike Lieberman

Toy made with no plastic junk. (3 letters)
— Joon Pahk

Taken control. (7 letters)
— Erik Agard

Of course it’s BOUNCER KEN PLACEBO, I mean, what else could it possibly be?

Click that’s often doubled. (3 letters)
— Byron Walden

In my blistering takedown of palindromes (GWQ No. 222, for real), I complained that the word wasn’t what it described — and indeed, a semordnilap is a word that reads differently in each direction. Supervocalics demand better, in the form of phrases that include A,E,I,O and U, a category that includes the word supervocalic. Go easy on this community, as they’re still grieving Phil Donahue. And even better are the euryvocalics, who include Y because the prefix “eury-” means a broad range and love the Vampire Weekend song Diane Young. And the answer to the above is TSK.

Second derivative function. (5,5,5 letters)
— Brooke Husic

There is a wonderful deep wit crossover between rap geeks and crossword nerds. Exhibit A: The rapper Ski Mask the Slump God, whose name is what Sherwin calls a perfect five, with one vowel per word (even if he claims he picked it because of his addiction to the palindrome Xanax). And then there’s the late rapper MF Doom, who built his rhymes with crossword-worthy references. Also, the answer is AFTER AFTER PARTY.

Resolve a tense situation. (4 letters)
— Erik Agard

I’ve only discussed cryptic puzzles here, somehow not mentioning the gloriously dumb People Puzzler.  (Above answer: EDIT!) But I defer to Stephen Sondheim, who in 1968 helped import more complicated puzzles to the U.S. with a New York magazine diatribe against mere collections of vowel-rich esoterica. With cryptics, he argued, “the pleasures involved in solving it are the deeply satisfactory ones of following and matching a devious mind (that of the puzzle’s author) rather than the transitory ones of an encyclopedic memory.” I fall somewhere in the middle, appreciating that I know about tennis star Arthur ASHE and margarine synonym OLEO from doing simple puzzles but happy to hear how the Orca-award winners wring drops of brilliance out of their twisted brains. Per Sondheim: “It’s a matter of mental exercise, not academic clerk-work, and all it takes is inexhaustible patience, limitless time and a warped mind.”

Brothers? (8, 5 letters)
— Ricky Cruz

---

Riposte Card: NYC nan or flan (4 letters)

The September Riposte Card, an honest-to-greatness printed piece of art that I mail to paid subscribers, is coming soon! The artist is Melanie Lambrick, big-time illustrator and creator of the mushroom gif seen above, and the quip she’s riffed upon is by FRAN, as in Lebowitz, not Drescher. More details next week, but in the meantime, upgrade your subscription to ensure you’re on the list!

---

 Quote Vote

Listen carefully, or a sexual perversion. (5,2,4,4 letters)
— Financial Times, c. 1974

There’s been an active discussion in the comments regarding whether paid subscribers have undue influence in proposing topics, so let me address the contentious issue: They absolutely do! Craig got his crosswords, Matt got gambling, and who knows, maybe the future will belong to Michael. But there are five slots in the Quote Vote each week and all submissions are welcome! Vote below, write in below that, buy a subscription, tap the heart, and then take a deep breath: There’s always next week!

---

Issue No. 270 of Get Wit Quick knows that sandwich cookies are always OREOS and never PEEK FREANS. If you’ve read this far, you’re probably looking for answers to the above two clues, which are diabolical: For “Brothers?” try pronouncing it BROTHers but still grit your teeth when I tell you the answer is BOUILLON CUBES. For “Listen carefully…” the answer is PRICK UP YOUR EARS, which is dirty enough to be apocryphal but there you go. Zach Sherwin posts a wordplay video six days a week on his TikTok, YouTube, and Instagram, but he refused to tell me which six. My book Elements of Wit: Mastering The Art of Being Interesting features a supervocalic on every page, or else. Tapping the ❤️  below is easier than even a Monday puzzle.