The Art of Crafting Crossword Puzzles: Insights from an Oregon Puzzle Creator

Crossword puzzles are a beloved pastime for many people, but what goes into creating a captivating puzzle? Matt Jones, a seasoned crossword creator with nearly three decades of experience, shares his journey and thoughts on crafting engaging puzzles.
A Lifelong Passion
Matt Jones’s fascination with crossword puzzles began in elementary school when he stumbled upon a stack of “Games” magazines left by a teacher in a classroom. The allure of these puzzles never waned, and as a teenager, he decided to try his hand at crafting them for submission to various publications.
“I didn’t think I had a chance,” Jones admits. “I was 15 at the time, probably… and I didn’t know if my quality level was right there just yet.” However, after a few attempts, his puzzle was published in The New York Times when he was a mere 19 years old. In those pre-email notification days of the 1990s, Jones received a personalized message from the Times’ renowned puzzle editor, Will Shortz.
Recounting the moment, Jones says, “You get a letter… saying, ‘This is great, congratulations, you’re going to actually be in the paper.’ I think I (still) have that letter somewhere.” Since then, Jones has created and published an impressive 1,163 crosswords.
Jonesin’ and the Alt-Weekly Puzzle Revolution
Jones’s weekly puzzle, aptly named “Jonesin’,” has graced the pages of alternative weeklies nationwide, including Willamette Week, since 2001. Back then, most alt-weeklies featured crosswords similar to those in publications like The New York Times. However, Jones and fellow puzzle writer Matt Gaffney sought to inject a bit of edginess into their puzzles to align with the magazines’ more daring content.
Reflecting on the early days, Jones says, “When we were first going about it, he was like, ‘I want to make this as subversive as possible. It’s going to have R-rated references and, you know, drugs, sex, rock and roll.'” Over time, the puzzles have evolved and mellowed, while still striving to maintain a unique character.
Keeping Clues Fresh and Relevant
Jones remains committed to keeping his crossword clues contemporary by staying in tune with trivia and pop culture trends. However, he acknowledges that he may occasionally slip with references from the ’90s, given his deep-rooted understanding with that era. While he endeavors to absorb the ever-evolving cultural landscape, he humorously concedes that TikTok celebrities might not be his strong suit.
The Recipe for a Memorable Crossword
So, what constitutes a great crossword puzzle, according to Matt Jones? He emphasizes three key elements:
Exciting Clues
The clues must pique the solver’s interest, prompting them to delve deeper into the puzzle.
Fresh Language
The language used in the puzzle should be contemporary and vibrant, ensuring that solvers connect with the clues.
A truly outstanding crossword puzzle lingers in the solver’s mind well after it’s been solved. If you find yourself discussing the puzzle for at least 10 minutes after solving it, it’s a sign of a genuinely memorable crossword.
Matt Jones’s dedication to the art of crossword creation continues to captivate solvers across the country, leaving them with puzzles that are as intriguing as they are unforgettable.