"I didn't know what that meant," Reagle says with a laugh. "The dictionary just said 'self-abuse,' and I didn't know what that meant, either."
His first published puzzle ran in a scholastic magazine when he was in middle school. It was a journalism teacher who suggested Reagle quit messing around with kids' crossword contests and submit some of his work to the New York Times. And as 1965 become '66, at just shy of 16 years old, Reagle did, sending then-editor Margaret Farrar three puzzles.
Two were rejected on the basis of some questionable content — one featured the answer "dead as a doornail," the other "rotten in Denmark."
The third was accepted.
Reagle made ten bucks.
Since then, both the amount the Times pays for a crossword puzzle and Reagle's personal returns have increased dramatically. While living in Santa Monica, Calif. (where he met Haley) in the early '80s, he paid the bills writing for game shows. But Reagle was always selling puzzles, and a regular weekly gig for the San Francisco Examiner came through in '85, opening the doorway to syndication and crossword creation as a full-time career.
Now, the couple — who relocated to Tampa in the early '90s to care for Haley's ailing mother — makes a low-six-figure income, with Haley handling the business half of the operation.
"I hate puzzles," she says, laughing.
"If it weren't for her, I never would've made appointments with editors, flown to all these cities and said, 'Your crossword is crap, put this one in,'" says Reagle.
Reagle is perhaps the only self-syndicated crossword constructor working today. In addition to the paper and magazine appearances, Reagle and Haley publish their own series of puzzle books, waiting until the puzzles are seven or eight years old before compiling them (they retain the rights to all of Reagle's puzzles); they're up to 11 volumes, along with a book of the Japanese Sudoku number puzzles.
His knack for turning out challenging, high-quality crosswords is obviously a big part of Reagle's success. It's only half of the creative formula, however. The other half is his singular style — the humor, the refusal to employ the arcane, never-spoken words only found in crossword puzzles, the contemporary pop-culture references and letter manipulation and homonymous clues. Those are the things that attract the odd bored newspaper editor, and the thousands of diehard solvers looking for a little more personality in their puzzles. It's a bit like designer fashions, in a way — there are actually people out there who can instantly recognize, and indeed prefer to work on, "a Merl."
Clue: "Two reasons not to become a zookeeper"
Answer: "Monkey pee, monkey do"
"The new school — well, we've been around for 20 years — we think crosswords should be a game, instead of a test," says Reagle. "That's why we throw in anagrams, anything we can think of to make words entertaining. Bad puns, good puns, funny quotations. I get a lot of mileage out of Stephen Wright quotes.
"We try to make crosswords like Jeopardy, with some humor thrown in. You never see an answer like 'name three Philippine trees.' No one cares about Philippine trees except crossword dictionaries. You'll hear tough TV trivia, the latest movies, all kinds of contemporary stuff, which, for the longest time, you wouldn't see in crosswords much."
At the same time, Reagle realizes his target audience is by and large an older, reactionary one — to go too far in the name of updating the crossword style is to potentially alienate many solvers, a majority of whom are over 50. He tells horror stories of hate mail pouring in after various newspapers switched to his crossword, and of using current references he figured everyone would recognize (like Emeril Lagasse), only to be proven wrong. Plenty of people simply don't want their Sunday crossword habit messed with, but in terms of content, Reagle says it's a matter of getting a feel for where is the line.
And, sometimes, crossing it.
"There are people who've never heard a Sam Kinison routine," he says, with mild disbelief. "There are people who've never watched Seinfeld ... so if you make jokes about George or Elaine or the Soup Nazi, there are people who won't know what you're talking about. But it's a legit place to go, so you have to sort of ignore the people who think that shouldn't be in a puzzle. It's all grist for the mill ... I sometimes wonder, can I use the names of the little people in Time Bandits? Well, do I want to get hate mail or not?
"And if I think some things are interesting, and I just want to bring them to people, I'll use them. The words on the backs of the bombs in Dr. Strangelove — most people won't know that, but I'll put that in a crossword puzzle."