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 cruciverb.com, 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.

After I called Tausig for pointers on constructing puzzles, I went off to gin up some ideas. In a standard 15-by-15 puzzle, he said, ideally 40 squares, and at least 37, should be taken up by the theme. A general symmetry is desired: if one of the theme answers is 13 letters long, there should be another 13-letter entry to match it. And there should be at least three answers that correspond to the theme.

When filling a crossword grid, I suppose the old saw about writing what you know applies doubly—you’re literally restricted by what you know, though cheating is allowed. (Having specialized software voids the question altogether. Tausig uses a program called Crossword Constructor, with the computer suggesting words to insert into the ever dwindling blank spaces. It comes with a word list that Tausig can add to.) Whatever’s on the mind of a given constructor can affect the makeup of a grid, or the way that it’s clued. In 2007 Bill Clinton was invited to write clues for a Sunday Times puzzle that had been built by constructor Cathy Millhauser, who clearly had the former president in mind when she filled the grid. The theme was baby boomers; Clinton supplied the clue “Boomer’s update of a 1972 Carly Simon song?” to the answer YOU’RE SO VEINY. Of course Clinton has other well-known interests, and the puzzle also included entries for “Foreign lady friends” and “Those French girls” (AMIGAS and ELLES, respectively).

Ben Tausig, who writes the <i>Reader</i>'s Inkwell crossword, may regret being publicly involved with the creation of the puzzle <a href="/general/20120329/CHILLINOIS-by-Sam-Worley.pdf">Chillinois</a>
Ben Tausig, who writes the Reader‘s Inkwell crossword, may regret being publicly involved with the creation of the puzzle Chillinois

In Crossworld, Marc Romano notes the layers of cultural specificity in the solution to a vague clue like “2002 upset,” which he found in a puzzle by wunderkind constructor Brendan Emmett Quigley, who in 2007 was accused by the Boston Globe of “making the New York Times crossword hip.” The answer, SUPER BOWL XXXVI, he notes, requires the solver to know that, first, “Superbowls are numbered with Roman numerals and, second, that the thirty-sixth was an underdog victory pulled off by the New England Patriots.” And that’s sports. Everyone knows about sports.

Romano later finds out that Quigley, being from Boston, has an indigenous interest in the Patriots. He had also been watching the game while he built the puzzle.

What was I doing as I first attempted to build a puzzle of my own? As it happened I had just broken up with my boyfriend of three years, and so I was after the usual pursuits: listening to down-tempo music, drinking such whiskey that would make a cowboy blush, and reading textual analyses of the Elizabeth Bishop poem “One Art” on the Internet. The poem, a villanelle, is the one that starts out: “The art of losing isn’t hard to master”; Bishop follows the casual, almost playful tone almost to the end, when she switches to the second-person and confesses that “losing you” is, finally, a “disaster.” The effect is devastating. I started to wonder if I couldn’t build a crossword around the poem’s rhyme scheme, which involves the repetition of “-aster”: vaster, faster, disaster.

Plus, here was a chance for a good Chicago reference—one would obviously want an answer to be PLASTER CASTER, as in Cynthia Plaster Caster, the local groupie who makes plaster molds of the penises of rock stars. What else? BROOKE ASTOR, the New York heiress who died a few years ago at age 104. Symmetry is important in crosswords (constructors also speak often of “elegance”), so I’d need another 13-letter entry and another 11-letter entry, to match what I had so far. I cycled through a few ideas: GRANDMASTER, as in Flash, or chess; GHETTO BLASTER, too racist; WITH DISASTER, as in flirting—too long. Finally SANDBLASTER, the graffiti-fighting tool, and NOW DO IT FASTER, a phrase that seemed colloquial enough, though at this point I suspect it wouldn’t have made it past Ben Tausig’s editorial pen.

I never intended to show him this one, though. I just wanted a little practice. I gave the finished product to a couple of coworkers, who both finished it. Tausig told me later that unless it was for a poetry magazine or something, the theme was “a bit too specific.” In his book Gridlock Matt Gaffney talks about attempting to piece together an income by making themed puzzles for specialized magazines. It’s not high art. “I once paid my rent by writing a tabbies-themed crossword puzzle for a cat magazine,” he writes. “The clue for 18-across was ‘It might flatten when tabby’s angry’ and the answer was EAR. Not quite Michelangelo at the Sistine Chapel, but the check cleared, and I could always hope that time would bring better things.”

Margaret Farrar retired as the New York Times‘s puzzle editor in 1969 and was succeeded by Will Weng, who held the job until 1977. Of the four puzzle editors in the Times‘s history, Weng’s tenure was perhaps the least remarkable—he wasn’t a pioneer of the form like Farrar was, and he didn’t refine and popularize it to the extent of the current editor, Will Shortz. Certainly he didn’t have the chilling effect of his immediate successor, Eugene Maleska, a fearsome former Latin teacher. Maleska was a bane. His tenure was characterized by an overreliance on what cruciverbalists call “crosswordese,” needlessly abstruse clues and answers that hinder solution of the puzzle more than they help. In Cruciverbalism, Stanley Newman supplies an example. Maleska would’ve looked favorably, he thinks, on “Fibre of the gomuti palm,” the trickiest clue in Arthur Wynne’s inaugural word cross. In the post-Maleska era the clue might have been different: “Homer Simpson exclamation.” For both clues the answer is DOH.

Newman, a competitive puzzler, also began building crosswords during Maleska’s reign at the Times, and had a serious ax to grind. He starts Cruciverbalism with an account of an event known as the LOA incident, which he variously calls an “outrage” and an “atrocity.” Newman was upset that Maleska chose not to clue the answer LOA with reference to Hawaii’s Mauna Loa, both traditional and a kindness to solvers; instead the editor clued it as “Seat of Wayne County, Utah,” which, Newman notes, then had 364 inhabitants. “My apologies to the people of Loa,” he writes, “but ‘Seat of Wayne County, Utah’ was a useless piece of information that made it into the Times puzzle solely because Eugene Maleska took a pedant’s pleasure in flummoxing other people with obscure facts.”

Newman also edited the Crossworder’s Own Newsletter, a platform from which he “declared war” on Maleska. Not only were Maleska’s puzzles esoteric, Newman thought, they were also “defective.” In a newsletter feature called Keeping Up With the Times Department he pointed out each time the paper committed a “howler”—in his estimation, something like “issuing a puzzle with a theme that called for celebrities’ last names that are also cities (JOHN DENVER, JULIE LONDON) but boneheadedly included a country (JILL IRELAND).” Newman wasn’t alone in his distress over Maleska’s pedantry. He represented a movement of puzzlers that came to be called the new wave—younger enthusiasts who wanted crosswords to be, if not exactly easy, then at least not larded with useless, alien information.

Maleska was vanquished not by Newman’s newsletter but by death. He was replaced in 1993 by Will Shortz, who was born on an Arabian horse farm in Indiana and received a degree in “enigmatology.” Since the 70s Shortz had been the editor of Games magazine and the founder and host of the American Crossword Puzzle Tournament, which brought competitive puzzlers together for annual competition in a hotel in Stamford, Connecticut. It was depicted in the 2006 documentary Wordplay, and has since moved to Brooklyn.

Under Shortz, the puzzle caught up to pop culture, or started to. Romano notes that Shortz also “radically reinforced” the policy of presenting puzzles in ascending order of difficulty through the week, with Monday the easiest and Saturday the most diabolical (Sunday’s, a much larger puzzle, is supposed to be about on par with Thursday). A certain amount of crosswordese is unavoidable, which is why you see the name of Brian ENO so often in puzzles. Recently Matt Gaffney introduced a way to measure what he called the “Shortz Factor,” which relates to how often a vowel-rich famous person’s name appears in the Times. Others have calculated this honor not by frequency but by day of the week; the writer Sherman Alexie said that he’s been pleased to watch his name appear earlier in the week as his star rises.

Updated references notwithstanding, Times readers—it’s well known—will accept only so much cultural degradation. In 2006 assistant managing editor Allan Siegal reported receiving “dozens of angry messages from readers, as well as complaints from colleagues on the staff” about the answer SCUMBAG, which had appeared recently clued as “Scoundrel.” The complainants pointed out that “scumbag” is actually an arcane term for “condom.” In an article about the flap, Slate pointed out that when a congressman called Bill Clinton a “scumbag” in 1998, the paper had refused to print the term—instead it reported on the “use of a vulgarity for a condom to describe the President.” Will Shortz said that the possibility of controversy had “never crossed [his] mind” and that he wouldn’t use the word again.

Crosswords have a tradition of propriety. Matt Gaffney says that even uncomfortable, distinctly nonvulgar words like “cancer” are rare, even when clued as something like “Sign of the zodiac.” But the new wave has bestowed upon the form a little more casualness. In February the theme of a Wednesday puzzle involved adding an “s” in order to alter some common phrases—SINGLESS BAR, for instance, for “Pub with no karaoke.” In a blog post the New Yorker‘s Eric Konigsberg feigned offense at the answer MIDASS TOUCH, which was clued as “Cause of a sexual harassment complaint?” Crosswords used to be so staid; Konigsberg points out that now Shortz allows answers like GAYDAR, SPAZ, and JEWFRO.

The editor has, from time to time, been accused of having a tin ear. Recently a debate erupted on the Internet over whether Shortz had correctly clued the word ILLIN—”Wack, in hip-hop.” Freelance writer Julieanne Smolinski sent Shortz a letter of complaint (“not the same things, at all!”) to which he replied that he’d clued it “according to the Dictionary of American Slang, edited by Robert L. Chapman,” who, Smolinski riposted, was ten years dead. Smolinski said she thought the word had more positive connotations, citing her source as “the rapper T.I.”

“This is how I would use illin’,” she wrote:

Julieanne: Hello, new best friend Will Shortz, how are you today?

Will Shortz: Illin’.

Insofar as vulgarity is basically my native tongue, I had a hard time envisioning a cuss-free crossword puzzle, and a few early drafts included words like BADASS and ASSFACE. Of course, the more you fill the grid, the more circumscribed the remaining spaces become. Sometimes ASSFACE is the only word that works.

What else to fill the grid with? I envisioned something specific to Chicago—why not add the letters CH to some common phrases? TEACH FOR TWO, for instance. Tausig told me he thought this was a good idea, though in his opinion adding CHI would be more “evocative.” (True, but outside of my skill set.) I couldn’t think of any phrases where this would work; in an e-mail, he effortlessly tossed off two, LIONSMACHINE and CHIANTICHRIST. Following my own theme—the easy one—I also came up with PUNCH INTENDED; HITCH ME BABY, with apologies to Britney Spears; and what I hoped would be a local crowd-pleaser: BENCHJORAVSKY, as in Ben Joravsky, the Reader columnist (“Nickname for a sidelined Reader staffer?”). To fill the rest of the grid took a while, and some liberties: TO SUE (as in, a litigant’s intention), BAIN CEOS (group including Mitt Romney), and a personal favorite, BEST NACHOS. None of these ended up passing muster with Ben Tausig, but first I showed it to an assembled panel of two Reader staffers, one of whom pointed out an embarrassing mistake.

Everybody does it eventually. I’d spelled Ben Joravsky’s name wrong.

Among the other aforementioned clues, he wasn’t wild about HITCH ME BABY—it’s not the full name of the song, he said, and it’s not quite colloquial anyway. I took a highlighter to the answers that he wanted me to ditch and found them affecting all quadrants of the puzzle. It would be best to start from scratch. I jettisoned the old theme answers and came up with new ones: SPELLING BEECH, PRAISE CHALLAH, BITCH PART, and PERCHDIEM. I began to fill a new grid. I demolished the erasers on at least four pencils.

This time Ben Tausig took issue with PERCH DIEM—the grammar was off, he thought. A coworker had suggested the clue “Catch of the day?,” but Tausig pointed out that that would more accurately be styled as PERCH PER DIEM. SPELLING BEECH was also off the table. Out again with the yellow highlighter; back again to the pencil sharpener. There were fewer problem areas that time, but enough to necessitate a full rewrite. Tausig again suggested an investment in the proper software—”The slog of filling becomes a cinch, and fun at that,” he wrote in an e-mail. I was working under deadline, with two different editors. I ran two new theme answers by Tausig—LETS CHEAT and PUNCH INTENDED, which I was pleased to revive—and set to work. I turned in the final draft as an Excel spreadsheet. I was learning, bit by bit, to make this easier.

None of this will soon make it to the New York Times. Ben Tausig suggested that the natural end to any crossword-constructing project would be to sell the puzzle, but I gave first-publication rights on this one to the Reader, and don’t really have time to make another. Still, the project was its own sort of validation. For those of us with an intense volume of useless information in our heads, crosswords make the mind feel more like a reservoir than, say, a landfill—they give all the ephemera some veneer of usefulness.

I remember reading in the mid-90s (I was in middle school) that Martha Stewart, domestic deity, needs only four hours of sleep every night. In the intervening decade and a half, have I retained that exceedingly irrelevant tidbit? I have. Surely there’s a use for it. A Martha Stewart-themed puzzle, for instance, for Martha Stewart superfans. Location of Martha’s former Connecticut home? TURKEY HILL. Prison nickname? M DIDDY. Name of prizewinning chow chow? GENGHIS KHAN. It’s not the Sistine Chapel, as the man said.

Of course crosswords are as much about elegance and wordplay as they are about raw knowledge. The best ones please you with their humor, their witty self-confidence. Marc Romano talks in his book to a guy at the annual American Crossword Puzzle Tournament who theorizes that the enterprise is essentially primal, in the Freudian sense. “Think about it,” the guy says. “You have all these people who wake up and say to themselves, ‘Gee, I feel like filling up little holes with something today.’ You’d think they’d get it, but apparently they don’t.”

Twenty-five pages later Romano himself hauls Nabokov into the discussion—something about “the interplay among aesthetics, ethics, and metaphysics within” that links his work to crossword puzzles—but I was pretty much skimming at that point. There’s really only so much you want to retain.