The puzzler and the puzzled | Feature | Chicago Reader

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The puzzler and the puzzled

In which our writer searches through, down, and across the history of crosswords for clues on constructing his own


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Spoiler alert: Some of the answers to Sam Worley's crossword puzzle (PDF) are discussed in this article. If you're the type of person who worries about that sort of thing, you're advised to do the puzzle first.

A month ago, I dropped the word SAVANT into the first crossword puzzle I ever tried constructing, hoping it would be some sort of talisman. It wasn't. It turns out there are no shortcuts in crossword building, and moreover I was going at the process backward. There are things to get out of the way before one fills the grid in earnest. Or, if you prefer, "before one grids." Some lingo comes with this territory. To "clue" is to write the clues. The "fill" (noun) refers to the words that make up the grid, and "grid" in this formulation can become an intransitive verb—"People definitely grid by hand," a crossword constructor told me when I asked him if I could use a pencil.

Though software exists to aid the gridding process, I went the discount route with a pencil, which is its own sort of adventure. I made my first attempt on a Tuesday night, waiting at my desk for the close of the week's editorial cycle, and I used blue lead, for which actual newsroom uses are dwindling. From the perspective of the constructor the tool of choice is a matter of pragmatics. From the perspective of the solver, the question of pencil or pen is a barometer of verve—Jon Stewart once joked that he completes crosswords in glue stick.

For either party the typical grid comprises 15 squares on each axis, the size of the New York Times's weekday puzzle. The Times didn't invent the crossword, but it's the publication most closely associated with it—ever since Margaret Farrar, the paper's first puzzle editor, nailed some cruciverbalist theses to the door of the puzzling world. To wit: No words shorter than three letters. Black squares should account for no more than 30 percent of the grid. Crosswords should be contiguous—no area an island—and symmetrical when rotated 180 degrees. The clue and the answer should be able to stand in for one another in a sentence.

Farrar began her career as Margaret Petherbridge, later taking her married name from John Farrar, a founder of publishing house Farrar, Straus and Giroux. She was a secretary to an editor at the Sunday World, which in 1913 printed the world's first crossword—the creation of an ex-Liverpudlian named Arthur Wynne, who conceived it initially as a diamond-shaped puzzle with no black squares. "Liverpool's two greatest gifts to the world of popular culture are the Beatles and Arthur Wynne," crossword constructor Stanley Newman wrote in his 2006 book Cruciverbalism: A Crossword Fanatic's Guide to Life in the Grid. The crossword's form would change and so would its name. Wynne called his creation a "word cross"; the linguistic inversion is thought to have been in error.

There were a number of errors in the early puzzles. Part of Farrar's job as secretary was to find and fix, though later in her career she'd admit to mistakes of her own. She once switched "Long John Silver" to "Captain Ahab" for a clue about a wooden leg, Farrar said in 1959 when she sat for an interview with the New Yorker, ensconced in her office, smoking cigarettes. "I got a letter from an eight-year-old boy complaining that while he'd found that the only answer that fitted was 'wooden leg,' as a reader of 'Moby Dick' he knew that Captain Ahab had an ivory leg. Perfectly true, but I couldn't help wondering, rather testily, what an eight-year-old was doing reading 'Moby Dick.'" Wynne retired in 1918 and Farrar was his successor. She had no native interest in puzzling but found what Newman guesses to be "love at first cite."

In 1924 Farrar edited the first-ever book of crosswords, which was also the first volume from the fledgling publishing house Simon & Schuster. Ahead of publication, though, Richard Simon and Max Schuster worried that the project would be a flop—that they'd embarrass themselves with a silly debut—and they had it printed under an alias. A sharpened pencil was attached to each copy. The first run sold out so quickly that they were moved to stamp their names on subsequent runs: a bona fide crossword craze had befallen the United States. Or, as Marc Romano puts it in his book Crossworld: One Man's Journey Into America's Crossword Obsession, "nothing was too frivolous to occupy the attention of a nation bathed in money and reveling in its newfound status as, arguably, the greatest military and economic power on earth."

In 1931 the New Yorker speculated on another reason for crosswords' popularity in a Talk of the Town piece. The occasion was the restaurant Huyler's printing puzzles on paper doilies—"so that one may occupy one's time pleasantly while taking refreshment." The New Yorker surmised, "This is a direct result of prohibition. When wine and beer were the beverages at a public inn, there was no necessity to engage the mind in any exercise—one merely allowed it to expand and subtilize. Now the drink is frosted chocolate, and the mind creeps for shelter into its own gray crannies, aided by a crossword puzzle (down and across, down and across) to escape the larger stratospheres of thought."

Crosswords were also, it appears, a peculiarly Manhattan divertissement, and 20 years later the New Yorker was still bitching about them. By 1942 Margaret Farrar had joined the Times, which in 1950 added a daily puzzle. For that decision the New Yorker could "figure out no logical conclusion, unless it is that the Times was embarrassed at sharing solely with the Daily Worker, among local papers, the distinction of not having such a frivolous feature."

Among Farrar's innovations was the introduction of the themed crossword, in which several entries are given over in the service of what she called an "inner-clue puzzle"—a bit of wordplay, a trick, a series of puns. She credited constructor Harold T. Bers with inventing the themed puzzle. An early example by Bers—possibly the first ever; sources differ on this point—was a puzzle entitled "Catalogue," which had answers like CATBIRD SEAT, KITTY HAWK, and PUSSYFOOT.

Ben Tausig, who constructs a puzzle that's syndicated in alt-weeklies including the Reader, told me that if I wanted to create a crossword puzzle I should start with the theme and worry afterward about the rest. I've always liked Tausig's puzzles—they're not too difficult to finish, but they put up a good resistance. And they're entertaining. As he notes on his website, he's "as committed to mild or explicit raciness as I am to contemporary references." Perhaps it was inevitable that Matt Gaffney, another puzzle maker, would in his book refer to Tausig as a "hipster" puzzler in the "edgy alternative weekly market."

Tausig, who's working on his PhD in ethnomusicology, began making puzzles in 2004. He was on a plane, doing the crossword in the airline magazine, and when he got stuck in a particular corner he filled it with his own answers. He started lurking on an e-mail list at, an online community for crossword enthusiasts, and began building his own, which he submitted to the likes of USA Today and the LA Times. He sent them to Will Shortz at the New York Times, too, but says that he realized he wanted to "write crossword puzzles that are for young people. Because a lot of the times you do the New York Times puzzle and it's a little bit old in sensibilities. They'll make references to old racehorses or old actresses." In 2004 he proposed a weekly puzzle in the San Francisco Bay Guardian; they bit. So did the Washington City Paper and the Village Voice. Tausig's puzzles began appearing in the Reader in 2005.

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