Why we’re obsessed with puzzles - and why AI can’t create them yet

The world of puzzles has evolved from humble educational tools to a multi-billion-dollar global industry, captivating millions with the challenge of crosswords and word games. The origins date back to the 1770s when John Spilsbury created "dissected maps" for students, an early iteration of the modern jigsaw puzzle. Over the centuries, puzzles matured into a diverse set of entertainments, from spelling bees and riddles to the enduringly popular crossword.

A key turning point for crosswords came in the 1940s when The New York Times, having previously dismissed them as "primitive," introduced its own crossword as a form of solace after the Pearl Harbor attack. Since then, puzzles have transcended distraction to become business drivers. The New York Times’ games division is now a core revenue source. According to a Statista report from February 2026, the NYT Games app generated around $11.2 million in in-app purchase revenue worldwide in the second quarter of 2024 alone, building on a partially subscription-based model.

The first official crossword was devised by Arthur Wynne in 1913 for the New York World, where a typographical error gave us the enduring "Cross Word" term. The global market for word games and logic puzzles, valued at $9.4 billion, is projected to more than double to $20.1 billion by 2034, according to Dataintelo’s ‘Word Games Market Outlook (2025–2034).’

Good crosswords are now seen as both art and entertainment, demanding equanimity between difficulty and solvability. Notable editors like Will Shortz, who designed his own degree in Enigmatology at Indiana University, emphasize the importance of fair, lively clues and grids that challenge but delight. Shortz recalls a favorite Election Day clue from 1996 that allowed for either "CLINTON" or "BOB DOLE" as legitimate answers based on the outcome, illustrating the ingenuity that enlivened the field.

The appeal of puzzles is deeply global and increasingly inclusive. Out of 13.35 million NYT Games subscribers as of mid-2026, over three million are outside the US. This demographic shift has pushed puzzle setters to reach beyond US-centric references and embrace more multicultural content, including Indian food, cities, and well-known personalities. Simultaneously, setters at outlets like the American Values Club Crossword have injected contemporary cultural references and opinions, while seeking to amuse and engage. As editor Ben Tausig notes, puzzles “always have some kind of a point of view,” unlike the traditionally objective approach favored by legacy newsrooms.

Puzzles have also begun to reflect broader social changes. Editors like Patti Varol at the Los Angeles Times Crossword seek to balance neutrality with inclusion, ensuring crosswords represent diverse perspectives, especially regarding gender and sexuality. The increased presence of women setters has altered clueing conventions, making the puzzles relatable to a wider audience.

The growth of digital platforms and international audiences continues to reshape the puzzle industry, ensuring that both the challenge and the joy of solving remain as relevant and accessible as ever. As the appetite for puzzles grows, so too does their power to bring people together in the pursuit of that elusive, satisfying answer.