Oregon crossword creator shares what he thinks makes a good puzzle

By Gemma DiCarlo (OPB)
Sept. 19, 2023 1 p.m.
A man in a black button-up shirt and glasses smiles at the camera.

Puzzle writer Matt Jones, shown here in a provided photo, has been making crossword puzzles for almost 30 years. His first published crossword appeared in The New York Times when he was just 19.

Courtesy Matt Jones

You may be an avid fan of solving crossword puzzles — but have you ever thought about what it takes to make them?


Matt Jones has been creating crosswords for almost 30 years. He’s been drawn to the puzzles since elementary school, when he found a stack of “Games” magazines left out by a teacher in a classroom.

By the time he was a teenager, he decided to try his hand at making the puzzles and submitting them to various publications.

“I didn’t think I had a chance,” Jones said. “I was 15 at the time, probably… and I didn’t know if my quality level was right there just yet.”

But after a few tries, Jones’ puzzle was published in The New York Times when he was just 19.

This was the 1990s, so there was no generic email notification of the acceptance. Instead, Jones received a personalized message from the Times’ legendary puzzle editor Will Shortz.

“You get a letter… saying, ‘This is great, congratulations, you’re going to actually be in the paper,’” he said. “I think I (still) have that letter somewhere.”


Since then, Jones has published 1,163 crosswords. His weekly puzzle, Jonesin’, has appeared in alt-weeklies across the country, including Willamette Week, since 2001.

At the time, most alt-weeklies carried the same crosswords that ran in publications like The New York Times. Jones and fellow puzzle writer Matt Gaffney wanted to create a crossword tailored to the edgier content in the magazines.

A black and white crossword grid.

A crossword grid photographed on September 11, 2023. Oregon crossword creator Matt Jones was interviewed on OPB's "Think Out Loud" on Tuesday, Sept. 12, 2023.

Gemma DiCarlo / OPB

“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,’” Jones said. “It has sort of mellowed out over the years.”

Jones still tries to keep his clues fresh by following along with trivia and pop culture trends. However, he admits that he’s not up to date on his TikTok celebrities.

“I try to absorb the culture as best I can, but you’re still going to get some ‘90s references sometimes,” he said.

As for what makes a good crossword, Jones said the clues have to be exciting, the language has to be fresh and, most importantly, the puzzle has to be memorable.

“If you’re talking about it at least 10 minutes after you’re done solving it, then that’s the sign of a really good crossword — if it sticks with you for that long,” he said.

Crossword creator Matt Jones spoke to “Think Out Loud” host Dave Miller. Click play to listen to the whole conversation: