Think Out Loud

Longtime Portland crossword constructor shares what he thinks makes a good puzzle

By Gemma DiCarlo (OPB)
Sept. 11, 2023 9:51 p.m.

Broadcast: Tuesday, Sept. 12

A black and white crossword grid.

A crossword grid photographed on September 11, 2023. Portlander Matt Jones has been making crossword puzzles since his late teens, with one of his first puzzles appearing in The New York Times when he was just 19.

Gemma DiCarlo / OPB


You might be an avid crossword solver, but have you ever thought about what it takes to create them? Matt Jones has been making crossword puzzles since his late teens, with one of his first puzzles appearing in The New York Times when he was just 19. His weekly puzzle Jonesin’ has appeared in alt-weeklies across the country, including Willamette Week, since 2001. Jones joins us to share more about what it takes to be a crossword constructor and what he thinks makes a good puzzle.

Note: This transcript was computer generated and edited by a volunteer.

Dave Miller: This is Think Out Loud on OPB. I’m Dave Miller. We end today with Matt Jones. He is a cruciverbalist. It’s a 14-letter word that I learned about two hours ago. It means that he’s really into crossword puzzles. In his case, he creates them. His first New York Times puzzle was published when he was just 19 years old. He went on to start the weekly puzzle “Jonesin’” which has appeared in all weeklies across the country, including Willamette Week since 2001. He has now published 1,163 puzzles. Matt Jones. Congratulations and welcome.

Matt Jones: Well, thank you. It’s great to be here. Great to be back in Oregon.

Miller: Welcome back. Yeah, you just arrived two hours ago from a trip on the other side of the country. Do you remember when you saw your first crossword puzzle?

Jones: Oh, my gosh. It depends on an actual crossword puzzle or if you see the kind of crisscross looking ones that you get on the side of cereal boxes. Maybe that would have been the first one at one point. But quality ones? I think I would say right around age 10.

Miller: So, relatively, then did you enjoy playing them as a 10-year old?

Jones: Oh, yeah. I had a tag teacher that had a bunch of Games Magazines just strewn about the place thinking, oh, this is gonna be a great exercise for the kids to just pick up and read on their own. And I got really engrossed by the fact that there are crosswords in there. And just one thing led to the other.

Miller: And that other was not just doing them but making them. When did that happen? Because they’re really different. I mean, there are, I’m sure listening to us right now, many, many, many people who love filling in crossword puzzles. My guess is almost none of them, even if they thought every now and then that would be a fun clue, they haven’t gone and actually made a whole puzzle.

Jones: It’s like you got the whole rest of it to do too.

Miller: Yeah, so what was it about it that made you want to actually do it yourself?

Jones: Well, it’s kind of getting immersed in the whole world of crosswords. Once you start seeing all the people who are creating the crosswords, you start seeing some resources on how you can actually submit crosswords, there’s books out, there’s various different things. I didn’t think I had a chance, because, A) I was 15 at the time, probably mid-teenager, and B) I didn’t know if my quality level was there just yet. So I thought all right, I’m gonna try this out. I’m gonna see what kind of resources I can get and actually go in and check, say New York Times specs and see what they want submitted. I would say on my second or third try I got in. So there were some that got rejected right off the spot.

Miller: But second or third try, you were in. And you submitted the one that actually was published when you were 18, am I right? And it was published when you were 19?

Jones: That’s right.

Miller: So at that point, what was it like when you got that?

Jones: Yes, oh my gosh. I mean, you get a letter, an enthusiastic letter, from Will Shortz saying ‘this is great, congratulations, you’re gonna actually be in the paper.’ I think I have that letter somewhere and I mean

Miller: A physical letter, this is not an email?

Jones: Yeah, physical letters. Oh yeah, he was very much into personalized letters for every single puzzle that went out too. So if you got that letter, that was like a special thing.

Miller: What did Will Shortz mean to you as a 15 year old, as an 18 year old?

Jones: Oh well, he came in from the 80′s new wave that was in Games Magazine at the time. So you’ve got your predecessor in the New York Times, which was Eugene Maleska, who was known for, ‘if it isn’t in a reference book, it’s not worth being in my puzzle.’ So there was a whole thing. Oreo would never show up in a pre-Will Shortz puzzle because it’s a trademark and it’s not in a dictionary so it’s not a real word.

Miller: I mean it’s not like it’s a dirty word or an obscure reference. It was something that basically anybody solving a puzzle would have known. But it didn’t fit the style guidelines pre-Will Shortz?

Jones: And Maleska’s temperament and everything like that. If you read about him, you’ll see that he had some nasty letters.

Miller: But how did you, as an 18-year old, come up with references, clues, words that a 60-year old reader of the New York Times would likely have in their brain? Because I mean the audience for the New York Times then and now, it’s not 18 year olds.

Jones: Well, I start with a seed base. I think my first actual puzzle had Uma Thurman as 1-Across. So if you’re just well enough into cinema, you’re probably going to recognize the name in anything. And the things that were spelled out like ‘nine-one-one’ underneath it and ‘trolley car’. So there were recognizable things within the puzzle. With the first puzzle, as a young person, I thought, ‘oh, I’m gonna go ahead and put Coolio in a puzzle’ thinking that everybody is gonna know who Coolio is.’ That was quickly rebuffed. He didn’t even have more than one song out at the time. It’s like, you know, ‘we’re never going to know who this person is.’ So he ended up replacing that.

Miller: He? Will Shortz?

Jones: Yes, Will Shortz ended up replacing that.

Miller: Replacing something seems like a lot of work. These things are all meticulously put there. Every letter, basically, has to work in two different words. What happens if you get rid of Coolio?

Jones: What happens? Well, I mean, what happens if you get rid of Coolio is it didn’t make my puzzle as cool, I guess. I don’t know. But yeah, he replaced it with the biblical Judge Gallio who, on my side of things, I had never heard before. And I thought, ‘well all right, if he says that that’s what’s going in, that’s what’s going in.’

Miller: And how many rap songs did Gallio do?

Jones: Oh tons.

Miller: Zero [Laughing]. Over time, how would you describe the niche that you’ve carved out for yourself in terms of puzzle making?

Jones: It was a very unique niche in that I was approached by another puzzle writer, Matt Gaffney, who had been in the business for a long time. Great guy and he had this idea. Most of the puzzles that actually showed up in the alternative newsweeklies, like ‘Willamette Week’, are already repeats of the New York Times puzzle. So they were getting the things that the New York Times is famous for, having a what is called “the breakfast test”. It’s the case that you don’t put things in the puzzle that wouldn’t pass the, sitting around breakfast and not offending people, test. So no war, death, pestilence, bodily functions, you know, that sort of thing.

Miller: Which is very different from the style of alt weeklies in general. I mean, the whole ethos of alt weeklies is almost the opposite.

Jones: So we thought, well, why don’t we try something that actually is tailored to that ethos and go with that. So our first attempt, in 2001, when he was basically the editor, I was the writer at the time. When we were first going about it, he’s like, ‘I want to make this as subversive as possible and it’s going to have R rated references and drugs, sex, rock and roll, all the things combined,’ that sort of thing. And it has sort of mellowed out over the years depending on which newspapers want what. But that’s kind of where we started out.

Miller: Oh, so you actually could put expletives, swear words in puzzles before, up to a point?

Jones: Yes, we have the S word. We didn’t have the F word. So, yeah.

Miller: I appreciate your discretion as you’re describing this. Was that exciting to actually push the boundaries in what was acceptable in a crossword, a beloved, but in some ways, stodgy form?

Jones: Yes, I think so. I think this was like the next logical step from where everything was. In the 80′s you had people that were trying to buck the trend.

Miller: And put Oreo in?


Jones: And put Oreo in. Exactly. The 80′s was like the advent of pop culture. It was about movies, it was about names, famous people and everything like that. And I thought, well, you know, our generation, we have our names and our people and why don’t we go ahead and go with that?

Miller: I hadn’t thought of this but in that way, especially if pop culture references are a part of crosswords, it seems like even just putting them in was a part of the progression. But now that they are, you can really chart changes in society by looking at crosswords?

Jones: Yes, and oddly enough, I know that there are a lot of people who are really obsessively into saving the clues from the puzzle. So it’s almost like doing a little bit of an archaeology dig. You can go back and see what a clue would be from the 1940′s as opposed to here’s what a clue would be from the 80′s and so on. The things that fall out of favor, the things that are a little bit too cringy to refer to in modern times, you get to see a little bit of that too.

Miller: Regardless of who your audience is and what publications, I imagine you still have to have some best guess about what they’ll know [or] what they might know. And I mean, who are you making these puzzles for right now? What do you assume is general knowledge?

Jones: Oh, that’s, wow. Ok. Well, I keep up with trivia. I keep up with trying to see where the pulse is right now. I just realized right now, I’ve been with this for 22 years. That’s an entire generation of people that have gone by since I started up because I was putting in alternative rock references and people of the 90′s and 2000′s. I’m not really up on my tiktok celebrities. So if that comes up, I’ll really try. But you know, I try to absorb the culture as best I can, but you’re still gonna get some 90′s references.

Miller: And then I guess at a certain point, if all goes well, you’ll just be an old man making crossword puzzles, right? And there will be some…

Jones: Livin’ the dream [Laughter].

Miller: …whippersnapper who is doing stuff that you think ‘I don’t even know what you’re talking about.’

Jones: It’s like, wait a minute. I used to be the whippersnapper and now we got all these other kids out there. I don’t know.

Miller: Is part of your brain always thinking about wordplay and clues?

Jones: Yes, not necessarily clues all the time but anagrams. I was just at the airport and I saw that there was a vending machine that said, ‘fly refreshed’ or something. And I looked in and there’s the instrument, “lyre” right in the middle of ‘fly refreshed’. Right there.

Miller: And it wasn’t like you looked at it and thought, ‘how do I arrange the words?’ There is an unconscious part of your brain [where] it just happens?

Jones: Yeah. And it’s tough to turn off sometimes. But it is there and, yeah, sometimes if you see things that anagram to something cool, then that’s sometimes an inspiration for what I put in.

Miller: Do you write those down or do they just bump around in your brain until you get a pen?

Jones: It’s a little bit of everything. The inspiration comes from strange places sometimes.

Miller: Have you put words or clues in your puzzles just as little gifts or Easter eggs for your friends?

Jones: I have had maybe one or two not so obvious Easter eggs in some puzzles. But not really. No. I mean, I’ll have things that I enjoy that people sometimes if you go on to the websites that review the crosswords will complain about like, ‘he’s doing too much like British comedies and things that I’ve never heard of.’ But it’s things that I like and that I feel that people should know at this point. So, you know, it’s my gift to the world, I guess.

Miller: We asked folks on Facebook what they think makes a good crossword. Heidi Senior wrote, “Clever clues and themes. The New York Times ones where you have to put more than one letter in a square and sometimes a different word in each direction.” Patricia Miller said, “It’s vocabulary that makes a good puzzle”. Damon Nash said he needs “The time to do it. That’s what makes a good crossword”.

It’s a gigantic question. But what are some of the hallmarks, for you, of a really good crossword puzzle?

Jones: It’s got to be memorable. I mean, the very first thing is if you are talking about it at least 10 minutes after you’ve solved it, then that’s a sign of a really good crossword. If it sticks with you for that long. Things that spark, things that actually are exciting. They just don’t thud right on the page. You tend to see things with ‘ness’ and ‘less’ that you don’t see in really good crosswords.

Miller: Oh, you think there’s some crutches based on the English language?

Jones: I mean, if you’re gonna use ‘serouses’ or ‘senselessness.’ I know that they’re really good bottom entries. But they’re really boring words, to be honest with you.

Miller: How do you use computers these days?

Jones: Well, I was on the verge of starting with computers because I started out, actually, doing everything on graph paper. And there aren’t very many people who actually still do that at this point. I have a crossword program that actually helps arrange everything right now. And I don’t use it as a 100% product. I will use it as a tool to be able to find words, to be able to arrange things, to be able to optimize things too. So I’m not just going to say here’s a crossword. I’m gonna run it through once and then that’s the product. It goes through many, many changes and little tweaks along the way.

Miller: And the computer is a tool that can help you?

Jones: Yes.

Miller: There was a puzzle in the New York Times last week. And the conceit was that it had been written by an AI. And it had cheeky clues like ‘what this puzzle is definitely not, having been created by me, a real and true human being,’ and on and on. It was actually pretty clever. Does that reflect an actual anxiety among puzzle creators?

Jones: I was expecting this question and, to be honest, we’ve been dealing with the fact that our computer is going to replace us for the past maybe 25-30 years.

Miller: But that was before ChatGPT and surprised us.

Jones: But have you seen ChatGPT? You actually try to put in, ‘write me some crossword themes.’ It will give you like six words, none of them symmetrical, none of them following the rules, and the jokes just fall flat. So I think ChatGPT, if it is a viable solution, has a long way to go.

Miller: Have you tried creating British cryptic crosswords, which is a world that’s always confused me?

Jones: I love them. I do them a lot. There are US cryptics as well but it’s been off and on. There’s not really as big of a market for them. And I would do them more for fun than anything else if I made them.

Miller: So you mentioned the market. When KATU did a story about you as that 19-year old, with your first published New York Times piece, they noted that you got $75 for it. And that’s the most famous venue in this country for crosswords. I can only imagine how many dozens of hours that took you. What are the economics of crossword creating?

Jones: Oh, gosh. The economics is that you do it as a labor of love basically. I can count, probably on one hand, the number of people who do it as a full time professional gig. And if they’re doing that, they’re submitting to maybe 10-15 different publications at once. So that’s their job. They’ve got a lot in the hopper, so to speak.

Miller: What’s your next challenge?

Jones: My next challenge is writing puzzle number 1,164 I guess.

Miller: Just keeping it going?

Jones: Just keeping it going until I just pass out.


Miller: Matt Jones, it was a pleasure talking to you. Congratulations.

Jones: Thank you very much.

Miller: Matt Jones is a Portland based crossword constructor. He’s been doing “Jonesin” for 22 years now. You can see it in Willamette Week and many other alt weeklies all around the country.

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