Why we can’t stop solving puzzles — and why AI still can’t set them

Why we can't stop solving puzzles – and why AI still can't set them Meet the setters behind the toughest crossword clues, the art of the perfect 'aha' moment, and why technology is not yet a formidable rival to the human mind.

Key points

• Out of the 13.35 million total subscribers of NYT Games as of mid-2026, over three million live outside of the United States.
• The credit for the first crossword, though, goes to Arthur Wynne who created a diamond-shaped grid called 'Word Cross' for The New York World newspaper in 1913.
• Shortz's all-time favourite clue appeared in the New York Times on November 5, 1996.
• Around the 1770s, a man called John Spilsbury mounted a world map on a piece of wood.
• Ben Tausig of the AVCX (American Values Club), an independent puzzles and games outlet, agrees, Above all else, is the puzzle funny?

Riddle me this: I am home to angry words/ The key lies in a turn of phrase or between the lines/ those who open the right boxes find rare joy/ Who am I?

Around the 1770s, a man called John Spilsbury mounted a world map on a piece of wood. He cut it into arbitrary pieces to be put together by his students as an educational exercise. He called them dissected maps. Today we know it as a jigsaw puzzle, named after the tool applied to manufacture it. This possibly was the origin of puzzles as we know it.

Since then, puzzles have entertained us in different forms and shapes, from crosswords, riddles and spelling bees to logic, wordle and sudoku, both on analogue and digital versions.

In the 1940s, the New York Times (NYT) had introduced its crossword – after dismising it as a " primitive sort of mental development " two decades earlier – as a distraction in the bleak aftermath of the Pearl Harbor bombing, marking the beginning of puzzles as the entertainment phenomenon we know today. Today, the NYT's major revenue generator is its games subsidiary – NYT Games. A Statista report published in February 2026, observed, "In the second quarter of 2024, the NYT Games app. Generated concerning 11.2 million USD in in-app purchase revenues worldwide. The gaming app is partially subscription-based."

Notably, the credit for the first crossword, though, goes to Arthur Wynne who created a diamond-shaped grid called 'Word Cross' for The New York World newspaper in 1913. A subsequent typographic error printed the puzzle as Cross Word and has been called that since.

Today, globally, the word games and logic puzzle market is valued at $9.4 billion and is projected to more than double to $20.1 billion over the next decade, according to the Word Games Market Outlook (2025-2034) by Dataintelo.

For his readers, Wynne intended the crossword would offer an interactive and stimulating experience. As a combination of words and numbers are thrown into grids making us wrack our brains, sometimes in frustration, and at other times in anticipation, in pursuit of that singular 'aha' moment, and indeed, our minds today are tested for their dexterity.

There are individuals who are intelligent and then there are puzzle solvers. Their intelligence comes with a vat of patience, allowing them to see beyond, in between and underneath the surface. A solver is curious and their never-give-up attitude almost epitomises human resilience. But, without a good puzzle, there is no good solver.

Will Shortz, the editor of the NYT Crossword, equates a good puzzle with a work of art: an attractive crossword grid, full of interesting, colourful, lively vocabulary, where every square appears in two answers.

"The whole point of a puzzle is to entertain the solver. You want the solver to win, and you want to push the solver to reach that goal, " notes Shortz, 73. This person is arguably one of the few residents in the world to have a college degree in enigmatology, the academic study of puzzles, a major he designed himself at Indiana University. Benjamin's puzzle (AVCX Club, US).

Shortz's all-time favourite clue appeared in the New York Times on November 5, 1996. It was Election Day to call the race between Democrat Bill Clinton and Republican Bob Dole. The clue for the 7-letter ACROSS answer read: 'Lead Story in tomorrow's paper!' The DOWN clues from the answer was created such that it could be the name of either candidate (CLINTON or BOB DOLE)and the grid would still work.

It is a delicate balance – not so hard that it would create the solver provide up, but not so straightforward that it doesn't feel earned. Australian puzzle setter David Astle has the best analogy – an apple tree.

"You don't want a major bowl of apples sitting for you. You additionally don't want a tree that is not going to provide you any fruits. There are some low-hanging fruits that offer you the courage to keep climbing up the tree. Ultimately, it needs to be this slow surrender of delightful apples, " notes Astle. This person has had an illustrious career as a TV anchor, radio host and author.

Although his "gateway drug" into this world was riddles, simultaneously, the 64-year-old has been setting puzzles for publications such as The Sydney Morning Herald, The Age, The Canberra Times among others. Speaking of riddles, do you have the answer yet?

Notably, a good puzzle is as much a dopamine hit for the solver as it is for the setter, whose ultimate goal is to create a "satisfying play" achieved with clever clues, fresh angles, snappy language, smart wordplay and, finally, juicy answers. This much sought-after satisfaction depends not only in solving a puzzle but additionally in the fewer number of hints one requires to reach the goal. David Astle's puzzle (Australia).

At The Times (UK), for instance, the qualification for a puzzle setter is not so much the list on their resume. "We look for people who can write good, fair, concise clues but also have a very good, plausible surface meaning, " notes Mick Hodgkin, Puzzles Editor at The Times.

For context, the other non-negotiable characteristic of a good puzzle is its ability to evoke a triumphant chortle. "I'd like to create them laugh at some point. I really feel it's particularly good to have humour in a puzzle, " adds 66-year-old Hodgkin, recalling a funny crossword clue he liked. It was "Fly back from China in 747?" The answer? TANG, referencing the dynasty.

Ben Tausig of the AVCX (American Values Club), an independent puzzles and games outlet, agrees, "Above all else, is the puzzle funny? We want ideas that are humorous, that will put a smile on people's faces."

It was, nevertheless, a different time when Shortz, Astle and Hodgkin began setting puzzles. Each of them discovered puzzles in their local newspapers as young boys.

It was unlikely that a person in the UK would read an American or Australian newspaper, and the clues were often local references that individuals outside the community or geography would not necessarily understand. For instance, referring to the Brooklyn-Manhattan transit as BMT.

Today, we live in a different world. Out of the 13.35 million total subscribers of NYT Games as of mid-2026, over three million live outside of the United States. It means that while the lived knowledge of culture still remains largely elusive, the chances of a non-American accessing a crossword in an American paper have massively rose. This realisation has pushed setters to expand – albeit particularly gradually and often relying on stereotypes – their scope of inspiration to a more inclusive knowledge base, spanning age, culture and even gender.

Clues referencing Indian food items, cities and personalities frequently reappear in NYT and The Times (UK) crosswords. A Naan is: Indian flatbread; Sari: Traditional women's draped garment; Assam: Northeastern Indian state known for tea and silk production. A memorable double-meaning clue for the answer Gandhi in The Times (UK) was: 'Indian spinner who played a leading role in getting England out.'

Taken together, the developments around why we can't stop solving puzzles – and why AI still can't point to a situation that is still moving, and the coming days should bring more clarity.