The puzzler and the puzzled | Feature | Chicago Reader

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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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.

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