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Cryptic crosswords: A puzzling British obsession

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Are these the ultimate brain teasers? Norman Miller explores the appeal of cryptic crosswords – containing mind-bending clues that offer unique Eureka moments.
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Let's begin a playful language journey with a dip into the mind of John Halpern, whose brain-teasing puzzles grace the UK's top newspapers under various pseudonyms. Halpern tells me about the day he met his wife. "When she told me her name, the first thing I thought was it's an anagram of 'entail' – though I didn't tell her that!" he reveals. "Instead I asked where the name came from. She told me 'Armenia'. Most normal people would immediately think: 'Interesting – tell me something about Armenia'. Instead, my first thought was 'It's the word 'men' inside the word 'aria'. I see wordplay patterns in the street, on the bus, at parties."

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Cryptic crosswords uniquely combine creativity, knowledge and logic, with a plentiful dash of style and wit. In a TED talk at London's Royal Albert Hall in 2013, Halpern described them as a celebration of "the hidden magic within language".

"Cryptic crosswords comprise a compendium of different types of brain teaser, so you get a lot of variety within each puzzle – anagram clues, acronym, puns and riddles," says Kathryn Friedlander, who does research in cryptics at the University of Buckingham's School of Psychology. "The solver has to work out which are relevant to any clue before actually solving it."

And three-quarters of solvers in her studies describe cryptic crosswords as a uniquely satisfying puzzle form. "Solvers experience a powerful insight moment when they realise how the clue should actually be interpreted," says Friedlander. She calls this the Penny Drop Moment, from the old English expression for that 'Aha!' instant when you suddenly understand something that has been racking your brain. "It's a highly pleasurable kick which rewards the solver," says Friedlander.

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 – Stephen Sondheim

She is echoed by legendary musicals maestro Stephen Sondheim, a devotee of a kind of puzzle that has mysteriously never caught on in the US. In a 1968 New York magazine feature, the writer of theatre's sharpest songs praised what he called 'British puzzles'. "Mental re-punctuation is the essence of solving cryptic clues," Sondheim wrote. "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."

Solving cryptic crossword clues can match the feeling of reading the best detective stories (Credit: Getty Images)

Solving cryptic crossword clues can match the feeling of reading the best detective stories (Credit: Getty Images)

The breadth and fluidity of the language in which you're reading this article provides a vital springboard for cryptic crosswords. "English has far more words than many languages," says Helen Ougham, an expert solver who has twice won The Times National Crossword Championship. "This makes it especially well-suited to the wordplay and misdirection of cryptic crosswords. Wikipedia lists nine different spellings, and meanings, just for words pronounced 'air'!"

Making up the rules

The first crosswords with purely cryptic clues appeared in the 1920s, pioneered by Edward Powys Mathers. He established the principle, followed by many subsequent setters, of publishing under a pseudonym – in his case, the infamous 15th-Century Spanish Inquisition torturer 'Torquemada'.

It was an appropriate choice given the devilish difficulty of many of the 'Torquemada' puzzles that ran in The Observer until Mathers' death in 1939. A 2013 feature in The Spectator noted how the combined brain power of the entire teaching staff of Oxford's Balliol College failed to finish one particular puzzle.

One reason for their difficulty was Mathers' regular reliance on obscure references that assumed a specific classical education or professional background (Mathers was an Oxford-educated translator, poet and literary critic). In response, later setters set about establishing a more level playing field for solvers, by coming up with general 'rules' that would allow anyone to tackle clues relying on their wits and knowledge of English, rather than a posh education.

Alistair Ferguson Ritchie (aka 'Afrit') set out some of these principles of 'fairness' in his 1946 book Armchair Crosswords, which were then honed by acclaimed setter 'Ximenes' (Derrick Somerset Macnutt) in his 1966 book Ximenes on the Art of the Crossword Puzzle. Ritchie summed up the new ethos as: "You need not mean what you say, but you must say what you mean."

Despite seeming obscure to most, cryptic crosswords abide by certain rules (Credit: Getty Images)

Despite seeming obscure to most, cryptic crosswords abide by certain rules (Credit: Getty Images)

A neat primer for wannabe solvers on how this principle works in various kinds of cryptic clues was set out in a BBC Radio 4 podcast by leading contemporary setter Sarah Hayes, noted for the left-wing slant of her clues as The Guardian's 'Arachne'.

One type of clue relies on double definitions. An example would be: "Tours streets,/and wishes one hadn't" (4). The answer is 'rues', playing on a double meaning combining the French word for street with an English word for regret.

Then there are 'hidden word' clues, such as this rather fiendish example by Brian Greer (aka 'Brendan', 'Virgilius' and 'Jed' for papers like The Times and Independent): "Some job at hand? We'll soon see" (4, 3, 5).  The solution (underlined) is Bath and Wells, and the buried hint is the fact that 'see' is a word referring to a bishopric, of which Bath and Wells is a famed English example.

'Envelope' clues, meanwhile, use one word inside another. A brain-scrambling example is: "Artist's phone hacked by horrible woman" (7). The answer is Chagall – puzzled out by playing with 'hag' (horrible woman) inside 'call' (the phone reference), while also picking up the hint that an artist is involved in the solution.

Puzzles with style

As with any form of creative expression, cryptic crossword setters can showcase their own style, which devotees grow to appreciate as much as they might like an author or songwriter.

In his article on the joys of cryptics, Sondheim put the idea succinctly. "In the best puzzles, styles of clue-writing are distinctive, revealing special pockets of interest and small mannerisms, as in any prose style. The clues of the author who calls himself 'Ximenes' in the London Sunday Observer are, to the eye of a puzzle fan, as different from those in, say, The Guardian as Wilde is from Maugham." Or as a Sondheim musical differs from one composed by Andrew Lloyd-Webber.

Fittingly for such cleverly creative puzzles, cryptic crosswords have made telling appearances in British literature, particularly in murder mysteries. Famed fictional cop Inspector Morse was one devotee – hardly surprising given his creator Colin Dexter set cryptic crosswords for The Oxford Times. In Dorothy L Sayers' story The Fascinating Problem of Uncle Meleager's Will, sleuth Lord Peter Wimsey solves a crossword in order to solve the mystery, as do the protagonists in books by Agatha Christie (Curtain) and Ruth Rendell (One Across, Two Down).

The quirky creativity of cryptic crosswords also offers a beacon of hope for those worried at the way computers have proven superiority over humans at our most complex games like Go and poker – even with the latter drawing on psychological tricks like 'bluffing'. Computer programmes are even churning out passable efforts at formalised poetry forms like haiku or basic forms of jokes, such as puns.

Yet experts like Friedlander think cryptic crosswords are one arena no AI will ever truly master, thanks to their use of "aesthetically beautiful clues that incorporate subtle nuances of language to misdirect the reader... It will be this kind of deeply deceptive clue which AI will struggle to solve, and which the human brain, with its capacity for picking up hidden hints, puns and remotely associated concepts, will be able to execute much more successfully."

Bringing humans together 

Despite the image of solitary solvers puzzling over clues, cryptic crosswords actually often engender a distinctive community spirit of shared appreciation in the effort to decode each setter's tricks. One poignant illustration of the special unity of cryptic devotees was the outpouring of emotion when much-loved Guardian setter 'Araucaria' (Reverend John Graham) set clues in a 2013 puzzle whose solutions revealed that he was dying of cancer.

Halpern (pictured) has found ways to unite people through their love of cryptic crosswords (Credit: Norman Miller)

Halpern (pictured) has found ways to unite people through their love of cryptic crosswords (Credit: Norman Miller)

Now Halpern is using Covid lockdowns to create a new community, with Zoom events drawing more than 100 attendees at a time from around the world. "We have a great opportunity to build a strong community for people who might otherwise feel disconnected," he says. "At a time when we are talking more about mental health, getting people into puzzle solving – which can ward off dementia – has got to help."

Halpern insists coming together to solve clues is as playful and pleasing as the form's way with language. "It's a relaxing atmosphere. And when we are allowed once more to meet in 2021, I intend to run puzzle-creating walking holidays and other community-creating projects."

As someone who remains bemused by cryptic crosswords, I also take comfort from Halpern admitting that, however brilliant he is at making them up, he is not so good at solving them. "I'm  really poor! Solving and setting are like driving a car in opposite directions down the same street. I still have the L-plates, and hit the occasional lamp-post." Perhaps he could turn that into a clue.

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