Brendan Emmett Quigley is a multi-talented man. He not only makes typewriter music, but also makes crosswords (for the Dig, among others). And not just any crosswords—Red Sox crosswords. When not throwing curveballs at puzzle solvers, picking up Will Shortz's dry cleaning, wearing rad suits, or crossword-ifying Facebook memes, Quigley sometimes speaks with crossword-impaired individuals like ourselves. If you like what he has to say, you can see more of Quigley at the American Crossword Puzzle Tournament in NYC this weekend, or solve new puzzles three times a week at his website.
How did you get into making crossword puzzles?
I've been making them since '96... I had a crappy job in college where I had to photocopy documents for a law firm and they wouldn't let us listen to the radio going into my senior year, which was the only way I could pass the time. I'd always been sort of a puzzle person but I'd never really done crosswords. I thought, "I'll photocopy the Times crossword and that'll educate me for the whole day and it'll probably take me the whole day to do it." I got addicted to them after 3 months. I scraped by the last year in college, making puzzles.
Where do you get your words or clues from?
Well, you write what you know, but I also devour stuff, news and stories, from lots of different places. If something catches my eye, a new word, I think maybe I can develop a theme around that. Being an aware, alert, and literary person, you can find inspiration in just about anything. There's no "muse," no go-to technique.
How do you usually start your puzzles?
You develop a theme and then you develop the pattern around the theme. There are rules like symmetry and you can't have three-letter words and you can't repeat words and things like that. You design the pattern around the theme, working across and down at the same time until you get to the corners and then Bob's your uncle.
Do you think making puzzles is more of an art or a science?
A little of column A; a little of column B. It's really mathematical, you know, you're working with spatial relationships. You're working with art in the sense that words are put together in a certain way and the words are inflexible because you can't have any misspellings. You need the art and the worldly element of just being engrossed in the English language—and you do use some foreign languages, geography, names in the news. You need to be truly aware. But it is mostly mathematical at the end of the day because of the rules of symmetry, and when you're building [the puzzle], in order to put this there, it has to follow this pattern. There's a lot of planning: if I put a seven-letter entry here I have to put a seven-letter entry there, and so on.
Do your skills translate to other types of word games, like Scrabble?
There are people who are very good at Scrabble who are in puzzles, but not me. When I'm making a crossword I can draw upon all 26 letters at any given point. I can also do multi-word phrases, names, geography, foreign languages, all the stuff you can't use in Scrabble. Seven letters and that's it. And since words are my job, I have to beat the holy pants off people [in Scrabble]. I try to score impossibly high when I play, so I don't really like it that much. I tend to play a really jerky asshole defensive game, block off huge sections of the board and things like that. It's not much fun.
My wife likes Scrabble, but we have to spell colour with a u and that sort of thing for her. That's the other reason I don't like it, because she speaks the queen's English.
Are there are any good tools for creating puzzles? What would you recommend for people looking to get into puzzle creation?
Just do a lot of puzzles. That's where I would start. The competition nowadays is just through the roof. Puzzles that would be published 10 or 15 years ago probably wouldn't be published nowadays.
People don't just write books without having read whole libraries full of them, but there are people who think "I'm going to get into this [crossword] thing" and they've never solved puzzles before. If you really want to get into it, just solve them.
There's a piece of software called Crossword Compiler that basically takes care of all the mechanics for you. It's a tool that can do everything for you, but anyone who's good will just use it to sort of juggle the words and put their own thought and talent along with it. It's opened up grids that never would have been able to be done before... but at the same time we have all these pretenders who let the computer do all the work. There's more to it than that.
What did you think of Wordplay? Is it encouraging these pretenders?
They did a great job of capturing a very static thing, crosswords. Just being on a page, it's not very animated—and some of these people aren't very photogenic—but they did a great job of capturing it, and I think it definitely helped. I've been helping put together the American Crossword Puzzle Tournament and the attendance was through the roof because of movies like this.
Between the movie and blogs, we're in the middle of another renaissance, especially with Sudoku and all these crossword puzzle sites and Crossword Compiler. People have gotten excited about it again... Most people who are into making puzzles were excited about the movie drumming up interest.
What aspect of the upcoming American Crossword Puzzle Tournament are you most excited about?
Well, let's just say this year will be my biggest involvement in the tournament so far. And it's my other family reunion, so I'm gonna see everybody, and it's like the one opportunity where I can geek out and talk about crosswords and not have others roll their eyes in complete boredom.
How did you get involved with the Red Sox crossword puzzle book? Will there be books for other teams?
I've become an in-house cottage industry guy for Cider Mill. I've written a bunch of puzzle books for them. I don't know about the Celtics but I think the Pats are coming up, some other teams as well.
They were in the market to do some sports books, so we negotiated an opportunity to do it. It was interesting because I was trying to figure out a way to balance something that would be entertaining for someone interested in puzzles but also for someone who might not be that into puzzles, but into the Red Sox. It was a difficult task and I'm pretty sure I failed at both ends. I shouldn't say that, John would be mad at me.
I had to dive in and read about the history of all these teams. Put it this way... after having written the book, my wife's holiday party was at Fenway Park last year in the EMC Club, the big corporate office things. In it were all the Gold Gloves, all the Silver Slugger things, the MVP awards, even movies about Bobby Doer in the men's room, and it was just like, "I did a crossword about this, I did a crossword about that..."
What's the craziest puzzle you've been involved with?
Jesus, where do I begin? I made one on the current Facebook gimmick, the 25 random things about me. I had 25 answers that were all pertaining to me. And I tried to make it so that even if you didn't know me you could still theoretically get it. That was way too much work to put together because most puzzles have a handful of themed words—9 or 10 out of 78. To try to get 25 of them was a bit of a stretch.
I think the thing with a lot of people today is, they say, "Can you make a puzzle about X?" and no problem, I can do that. Then they ask, "So you can get all 78 entries to be about the theme?" And it's like no, you obviously have never done a crossword before in your life. I think that probably the biggest hurdle for a freelancer is telling people who want crosswords that what they're asking for is completely impossible. Things like having every entry about something, it's simply impossible.
I pitched a puzzle to ESPN and they didn't bite. I made 60% of the clues something to do with sports. That was just absurd, it was beyond the point of even solvability. There's a reason why you rely on the old standard words that appear all the time [in crosswords].
Can you talk about the Boston Typewriter Orchestra a little bit?
The DJ at my wedding is one of the founding members and he said we can always use you, so I formally joined... it must've been last year. It's just basically a drum circle and the office combined, with goofy banter in between. It's a lot of fun, it's always been fun. I've been in bands about as long as I've been doing crosswords, and the fact that this one is knowingly absurd, it is fun to be a part of.
Any parting words of advice for puzzlers?
For the uninitiated, they really are intended to be solved. Don't get frustrated, give 'em a shot. It's like going to a foreign country: you don't speak the language right away. They're all over the world and it's a very specialized vocabulary. If you stick it out your own vocabulary will grow and you'll come to appreciate these things.
Images from Amazon and dailyinvention and patrickeasters on Flickr. Check Quigley's website for puzzles.

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