Michael Crawford is far from the only person from the world of musical theatre …

How lucky those of us who devoted their lives to the theatre were to do so at the same time as Stephen Sondheim, getting to continually appreciate his gifts of genius songwriting and masterful art. -MC (2 of 2)

— Michael Crawford (@CrawfordMichael) November 27, 2021

… to have expressed this thought lately. The same goes, in a quieter way, for the world of crosswords. Crosswords, that is, of a particular kind.

Stephen Sondheim – playful, intelligently demotic – was no fan of the American-style puzzle, despite its being playful and intelligently demotic at its best. This may or may not be because he had a puzzle rejected by the New York Times when he was “14 or 15”; the reply letter described him as “obviously precocious”, which is how he learned that adjective.

In 1968, he urged readers of the New York magazine to instead seek the British-style cryptic:

A good clue can give you all the pleasures of being duped that a mystery story can. It has surface innocence, surprise, the revelation of a concealed meaning, and the catharsis of solution.

Let’s be a little more precise. During the pandemic, we have discussed in these pages a particular kind of cryptic crossword: the kind you notice at weekends that lacks black squares and repeatedly sends the solver to the dictionary, where the filled grid may be no more than the starting point for a startling endgame. We could euphemistically call these beasts “the engrossing puzzles” – it was to these that Sondheim was addicted in the 1950s.

Is “addicted” too strong a word? No: Sondheim’s habit was to buy (or, as he otherwise told it, retrieve from an inbound steamship) a copy of the BBC’s Listener magazine on a Thursday on the way to meet up with a colleague to write a musical, and the Listener’s puzzle (now adopted by the Saturday Times) is perhaps the most engrossing of all.

“I got Leonard Bernstein hooked,” he recalled in 2004. “Thursday afternoons, no work got done on West Side Story. We were doing the puzzle.” They may even have managed to rationalise this as not bunking off, given Sondheim’s description of composition: “You make a pattern out of a series of discrete bits of information and try to make it graceful so you won’t feel the effort behind it. In that sense, lyric writing is a puzzle.”

Here he is explaining what he thinks is the “nice thing about doing a crossword puzzle”:

Bernstein and Sondheim were among the lucky few to receive the privately circulated Apex (“a puzzle every Xmas”), also from the engrossing end of the crosswording spectrum. It was set by retired carpenter Eric Chalkley and is now the purview of another setter (“a Phi every Xmas”). Phi (who you can get to know here) has shared the 2010 Apex for those not in the distribution list. You can surely guess its theme, and you can read Sondheim’s letter in reply to Phi here.

On the topic of puzzles about Sondheim, his 85th birthday in 2015 was well celebrated by Guardian setters. Arachne (who you can get to know here) set a wonderful prize puzzle (with annotated solutions) …

19a Two idiots stripped Mini’s bumpers off (9)
[ definition: ones who bump off ]
[ wordplay: synonym for ‘idiot’, repeated + MINI without first & last letters (“stripped”) + S ]
[ ASS & ASS + IN + S ]

… to which Sondheim replied:

I look forward to avoiding work in order to solve it.
Steve S

Sondheim signed off as Steve! I did not see that coming. At the same time, the Sondheim Society commissioned Enigmatist (who you can get to know here) to create a custom puzzle. The society’s generous Craig Glenday has allowed us to share the extraordinary puzzle here. Craig also shared a titbit: he discussed with Sondheim a puzzle/musical/video game hybrid, but it did not come to be.

Of Enigmatist’s tribute, Sondheim said: “I’m determined not to tackle the puzzle until I finish the opening number of the new show, but it will be hard to resist (particularly since it looks moderately easy.)” He will have found later that it is not easy.

I’ll also mention an Enigmatic Variations puzzle from July by Sea-Kale titled The North American One, which I hope reached its subject, and an earlier entry in the same series: Resident Jokers by Owzat.

I’ve enjoyed all these immensely and will be spending Christmas finally going through all of the puzzles that resulted when Sondheim put his money where his mouth was, and set puzzles for the rest of us to solve. This was, he said later, to help a new publication to which his friend, Gloria Steinem, was a contributor.

As illustrated by the giddying grid accompanying this paragraph, they too are … engrossing. Forty-two of the beasts appeared in the New York magazine until his other job (specifically Company) diverted him from public setting, though I understand his party guests tended to be regaled with other kinds of puzzle. Here’s a sample, an example of New York content in a British kind of clue:

5. Mixtures of completely Yiddish sighs? (6)
[ definition: mixtures ]
[ wordplay: synonym of “completely” + Yiddish expressions of woe ]
[ ALL + OYS ]

The magazine celebrated its 40th birthday by reprinting the first three; the others have been digitised by Google Books. Animator Galen Fott has assiduously collated the relevant links in a blogpost and composer Colm Molloy has done likewise in a Twitter thread.

I’m not alone in diving into Sondheim’s puzzles as this wretched year ends. We can hope that the swell of enthusiasm might prompt whomever owns the relevant rights to republish the hens’-teeth collection in book form.

Let’s finish by making a mental note to watch the whodunnit Sondheim co-wrote with Anthony Perkins – and returning to Company with an addition to our collaborative playlist, Healing Music Recorded in 2020-21 to Accompany a Solve or Even Listen To:

• Here’s a collection of all our explainers, interviews and other helpful bits and bobs.

• The Shipping Forecast Puzzle Book by Alan Connor, which is partly but not predominantly cryptic, can be ordered from the Guardian Bookshop.

• Crossword blog will resume on 13 December.