5 Questions with Puzzle Master Will Shortz

Welcome to another edition of PuzzleNation Blog’s interview feature, 5 Questions!

We’re reaching out to puzzle constructors, video game writers and designers, writers, filmmakers, and puzzle enthusiasts from all walks of life, talking to people who make puzzles and people who enjoy them in the hopes of exploring the puzzle community as a whole.

And I’m overjoyed to have Will Shortz as our latest 5 Questions interviewee!

Without a doubt the most famous name in crosswords today, Will Shortz is the crossword editor for the New York Times, a position he’s held since 1993 (after putting in time with both GAMES Magazine and our friends at Penny/Dell Puzzles). In his time as editor, he’s been credited with spearheading a sharp decrease in crosswordese in Times puzzles, as well as offering a greater level of visibility and acknowledgment for individual constructors.

He continues to serve as the amiable face of crosswords across all forms of media — on the radio with NPR, on television in The Simpsons and How I Met Your Mother, and in theaters with the documentary Wordplay. (He even provided the Riddler’s puzzle clues that so bamboozled the Dark Knight in the film Batman Forever.)

But solvers interested in puzzles beyond crosswords will also have a treat in store for them in 2014! The folks at Penny Press have teamed up with Will to create Will Shortz’s WordPlay, a magazine featuring crafty variety puzzles and crossword variants created by some of today’s top constructors.

Will was gracious enough to take some time out to talk to us, so without further ado, let’s get to the interview!

5 Questions for Will Shortz

1.) As the world’s first (and only) degree-holding enigmatologist, was becoming the editor of the New York Times crossword always a goal you had in mind, or did you foresee yourself doing something else with your singular degree?

Since childhood I’d always planned a career in puzzles, just not as crossword editor for The Times. In fact, I didn’t envision a career with crosswords at all. I imagined myself in an attic or a tiny house somewhere making novelty puzzles and sending them out for publication — probably living in poverty, but doing what I wanted. I fell into puzzle editing without a lot of planning.

But I do have a law degree from the University of Virginia (J.D., 1977), so if puzzles ever end up not working out for me, I always have that to fall back on!

2.) The hundredth anniversary of the crossword is fast approaching. Given your familiarity with puzzles both past and present, what does the hundredth anniversary mean to you? And where do you think puzzles will be a hundred years from now?

I’m not good at predicting the future. But I will say that crosswords are the best and most flexible form of puzzle ever devised, because they involve language (which we all use) and connect with virtually everything in life. They can be made easy or hard, small or large, tricky or straightforward, topical or of general interest. There’s a crossword for everyone and every mood.

Also, there’s something very appealing about filling empty squares. As humans, I think we like to fill empty spaces, and doing that in a crossword seems to satisfy some elemental human need. Even if print media die someday, I think crosswords will probably exist forever in one form or another.

[Here, Will and constructor Merl Reagle appear with the Simpsons in a
promotional pic for the episode “Homer and Lisa Exchange Cross Words.”]

3.) I could ask you how far in advance you choose puzzles for publication (considering the Times’ famous incremental rise in difficulty throughout the week), or inquire about your work as NPR’s resident puzzle master, but to be honest, I’m more curious about what you do when you’re NOT doing puzzles. What other activities or hobbies do you enjoy?

As friends know, I’m almost as fanatical about table tennis as I am about puzzles (emphasis on *almost*). I own my own club — the Westchester Table Tennis Center, just north of New York City. It’s one of the largest table tennis facilities in North America, and I believe it’s the nicest (which I say having played in almost 200 clubs in 43 states and two Canadian provinces).

At the moment I’m close to finishing a personal goal — to play table tennis every day this year. As I write this (on Dec. 17), I’ve played every single day since Jan. 1 — 351 days in all. And I’m filming myself every day as proof. At the end of the year, if I succeed, some friends of mine in Hollywood have promised to edit a 3- or 4-minute video of me playing every day, which I’ll throw up on YouTube.

My ultimate goal is to become national table tennis champion for my age.

4.) What’s next for Will Shortz?

No plans for anything else. I love what I’m doing. I’ve been the crossword editor of The Times now for 20 years, overseer of the U.S. team for the World Puzzle Championship for 22 years, puzzlemaster for NPR’s “Weekend Edition” for almost 27 years, director of the American Crossword Puzzle Tournament for 36 years, and program director for the annual convention of the National Puzzlers’ League for 38 years. That’s plenty to keep me occupied.

5.) If you could give the readers, writers, and puzzle fans in the audience one piece of advice, what would it be?

I have two goals in life: One, to make the world a little better for being here. And Two, to enjoy myself. I think that’s a good philosophy for anyone.

Many thanks to Will for his time. You can follow him on Twitter (@Will_Shortz) and listen to his NPR appearances on Weekend Edition here! And keep your eyes peeled for the first issue of Will Shortz’s WordPlay, which will be hitting newsstands in February!

Oh, and I suppose you could always check out the New York Times Crossword, if you’re so inclined. =)

Thanks for visiting the PuzzleNation blog today! You can like us on Facebookfollow us on Twitter, cruise our boards on Pinterest, check out our Tumblr, download our Classic Word Search iBook (recently featured by Apple in the Made for iBooks category!), play our games at PuzzleNation.com, or contact us here at the blog!

Crossword History: A Timeline

The hundredth anniversary of the crossword is nearly upon us, and we at PuzzleNation Blog thought we’d take a look at the long (yet surprisingly short) road it took to get to this marvelous centennial!

And so, without further ado or folderol, we proudly present:

A Brief History of the Crossword
(by Glenn Dallas and the PuzzleNation Team)

16th – 11th century BC

Inscriptions from New Kingdom-era Egypt (Eighteenth to Twentieth Dynasties) of horizontal and vertical lines of text divided into equal squares, that can be read both across the rows and down the columns, are made. These inscriptions are later referred to by Egyptologists as “Egyptian crossword puzzles.”

19th century

Rudimentary crosswords, similar to word squares, begin appearing in England, and later elsewhere in Europe.

June 22, 1871

Future inventor of the crossword, Arthur Wynne, is born.

March 23, 1897

Future New York Times crossword editor Margaret Farrar is born.

February 25, 1907

Future New York Times crossword editor Will Weng is born.

December 21, 1913

The New York World publishes the first crossword, invented by Liverpool journalist Arthur Wynne.
(The puzzle is originally known as a word-cross.)

January 6, 1916

Future New York Times crossword editor Eugene T. Maleska is born.

1920

Margaret Farrar is hired by The New York World as a secretary, but soon finds herself assisting Arthur Wynne with proofreading puzzles. Her puzzles soon exceed Wynne’s in popularity.

Colonel H.W. Hill publishes the first Crossword Dictionary.

1924

Margaret Farrar publishes the first book of crossword puzzles under contract for Richard L. Simon and Max Schuster, “The Cross-Word Puzzle Book.” It was an instant bestseller, launching Simon & Schuster as a major publisher.

The Sunday Express becomes the first newspaper in the United Kingdom to carry crosswords.

1926

The cryptic crossword is invented by Edward Powys Mathers, who uses the pseudonym of Torquemada. He devises them for The Observer newspaper.

1931

Dell Puzzle Magazines begins publishing.
(Dell Publishing itself was founded in 1921.)

1941

Dell Pocket Crossword Puzzles first published.
(The magazine continues to this day.)

February 15, 1942

The New York Times runs its first Sunday edition crossword. (Click here to read more about this.)

June 2, 1944

Physics teacher and crossword constructor Leonard Dawe is questioned by authorities after several words coinciding with D-Day invasion plans appear in London’s Daily Telegraph. (Click here to read more about this.)

1950

The crossword becomes a daily feature in the New York Times.

August 26, 1952

Future New York Times crossword editor Will Shortz is born.

1968

Lyricist Stephen Sondheim begins creating cryptic crosswords for New York Magazine, helping introduce Americans to British-style crosswords.

1969

Will Weng succeeds Margaret Farrar as the second crossword editor for the New York Times.

1973

Penny Press is founded.

1977

Eugene T. Maleska succeeds Will Weng as the third crossword editor for the New York Times.

1978

First year of the American Crossword Puzzle Tournament,
later featured in the documentary Wordplay.

1979

Howard Garns creates the modern Sudoku puzzle for Dell Magazines (under the name Number Place), the first pen-and-paper puzzle to rival the crossword in popularity (though this spike in popularity would occur decades later under the name Sudoku).

June 11, 1984

Margaret Farrar, while working on the 134th volume in Simon & Schuster’s crossword puzzle book series, passes away.

1993

Will Shortz succeeds Eugene T. Maleska as the fourth crossword editor for the New York Times.

November 5, 1996

One of the most clever and famous crosswords of all time is published, the election-preceding crossword where either BOB DOLE ELECTED or CLINTON ELECTED could read out, depending on the solver’s answers.

June 23, 2006

Wordplay documentary hits theaters, featuring both celebrity solvers of crosswords and the participants and organizers of the 2005 American Crossword Puzzle Tournament.

February 29 – March 2, 2008

Thanks in part to the Wordplay documentary, the American Crossword Puzzle Tournament outgrows its previous setting and moves to Brooklyn.

June 6, 2008

Matt Gaffney launches his Weekly Crossword Contest (MGWCC).

August 2008

Lollapuzzoola, a crossword-solving tournament with a more tongue-in-cheek, freeform style, launches in Jackson Heights, New York.

October 6th, 2008

Patrick Blindauer’s famous dollar bill-inspired crossword puzzle is published.

2009

The city of Lvov, Ukraine, creates a crossword that spans an entire side of a 100-foot-tall residential building, with clues scattered around the city’s major landmarks and attractions. It’s awesome.

October 11th, 2011

PuzzleNation.com goes live.

June 2012

David Steinberg launches the Pre-Shortzian Puzzle Project, intending to create a complete database of every New York Times crossword.

August 13th, 2012

PuzzleNation Blog is launched.

June 14th, 2013

Matt Gaffney celebrates five years of MGWCC,
stating that MGWCC will run for 1000 weeks
(which puts the final edition around August 6th, 2027).

December 21st, 2013

The Crossword officially turns one hundred years old.


Additional information:

February 15th, 1942: The New York Times initially regarded crosswords as frivolous, calling them “a primitive form of mental exercise”; the motivating impulse for the Times to finally run the puzzle (which took over 20 years even though its publisher, Arthur Hays Sulzberger, was a longtime crossword fan) appears to have been the bombing of Pearl Harbor.

In a memo dated December 18, 1941, an editor conceded that the puzzle deserved space in the paper, considering what was happening elsewhere in the world and that readers might need something to occupy themselves during blackouts. The puzzle proved popular, and Sulzberger himself would author a Times puzzle before the year was out.

June 2nd, 1944: The words Omaha (codename for one of Normandy’s beaches), Utah (another Normandy beach codename), Overlord (the name for the plan to land at Normandy on June 6th), mulberry (nickname for a portable harbor built for D-Day), and Neptune (name for the naval portion of the invasion) all appeared in Daily Telegraph crosswords during the month preceding the D-Day landing.

This has been attributed to either an incredible coincidence or Dawe somehow overhearing these words (possibly slipped by soldiers involved) and incorporating them into puzzles unwittingly.


Thanks for visiting the PuzzleNation blog today! You can like us on Facebook, follow us on Twitter, cruise our boards on Pinterest, check out our Classic Word Search iBook (recently featured by Apple in the Made for iBooks category!), play our games at PuzzleNation.com, or contact us here at the blog!

Let’s Make Our Own Crosswords, Part Two: Advice!

On Tuesday, I posted an introductory how-to for creating your own crossword puzzles. All of the advice and guidance was based on my own constructing instincts and work I’ve done over the years.

But I’m just one puzzler, and I figured why not reach out to other constructors and editors in the puzzling community and see what helpful suggestions they had for aspiring puzzle constructors.

So today, I put you into the good hands of professionals and topnotch puzzlers, as they walk you through the do’s and do-not-do’s of crossword construction. As constructor Ian Livengood said, “it’s more art than science,” but with the advice of established constructors in your pocket, you’ll be off to a great start.

And as it turns out, they’ve got plenty of worthwhile nuggets of advice to offer! In fact, they had so much to say (and I wanted to include so much more!) that I’ve broken up the advice by topic and put each one on its own page. Just click on the links below to take you to a treasure trove of puzzly wisdom!

Good luck, my fellow puzzlers!

And thank you to David Steinberg, Robin Stears, Ian Livengood, Rich Norris, Patti Varol, Doug Peterson, and Eileen Saunders for their masterful advice!

Thanks for visiting the PuzzleNation blog today! You can like us on Facebook, follow us on Twitter, cruise our boards on Pinterest, check out our Classic Word Search iBook (recently featured by Apple in the Made for iBooks category!), play our games at PuzzleNation.com, or contact us here at the blog!

How to Make a Crossword: Choosing a Theme

“Themes are the hardest part of the construction process. Filling the grid and writing the clues takes perseverance, but coming up with a theme requires that elusive spark of inspiration.” — constructor Doug Peterson

This sentiment was echoed by other constructors I spoke with. Crossword guru Eileen Saunders said, “The hardest part of constructing a puzzle (for me) is coming with the theme. After that, everything else seems to fall into place.”

Los Angeles Times Crossword Editor Rich Norris and assistant Patti Varol: “Originality is an important element of a good theme, but sometimes originality means lively themers in a chestnut gimmick or a clever spin on familiar wordplay.

“Originality, themewise, is not always ground-breaking, or innovative, or even original. A good theme always has sparkle, with lively, idiomatic phrases that will resonate with a majority of solvers.”

New York Times Crossword constructor Ian Livengood discusses how to choose theme entries: “Once you think of a potentially good theme, it’s vital to see if something similar has been done before. What’s the point of having databases, right? If the theme looks interesting and relatively new, you must make sure the theme is consistent.

“For example, if you are doing two-word phrases that start with the letter P and you’ve got PLEDGE PIN, PARK PLACE, PLUM PUDDING, PINK PANTHER and … PARAKEET, that’s a problem. The single word breaks the pattern and confuses solvers. So consistancy and freshness is very important.”

Rich and Patti also mentioned consistency and balance as critical elements of a good theme. “One odd entry can ruin an otherwise great idea: a themer that ends with the theme’s key word when all the others begin with it, a stray plural in a set of singular phrases, a noun phrase in a group of verbs, a song title in a set of movie titles, a rhyming pun in the mix with spelling-change puns.”

I think I’ll give Doug the final word on coming up with a theme for your puzzle. “If you think a theme entry is humdrum or doesn’t quite fit with the others, it’s time to put your brainstorming cap back on. Remember, your first job is to entertain the solver, so make that theme sparkle.”

How to Make a Crossword: Grid and Fill Advice

When it comes to grid building, constructor Ian Livengood considers it “perhaps the most important aspect of construction.” And since building a grid and placing your theme entries goes hand-in-hand, I’ve opted to combine them into one section.

Ian continues, “Try to avoid a pileup of black squares and 3-letter word concentrations. Once you put the theme answers in the grid, manipulate the black squares to avoid any potential trouble spots. Trouble spots are letter patterns that are highly unusual, and therefore, difficult to fill. If, for example, you have the letter sequence ??DK? in a puzzle, the only acceptable fill is VODKA. Well, you better make sure VODKA will work in the surrounding area, otherwise you’ll have to start over. It’s always better move blocks around before trying to fill the puzzle.

“After locking in words with unusual letter patterns, place your longer non-theme entries in the puzzle. You must make these entries ‘pop.’ That is, they really should be interesting. HATCHET JOB or THE JIG IS UP, for example, would be fun entries to fill in. REPOSSESSED, on the other hand, is a total snoozer.

“Minimize crosswordese and try to make the vocabulary accessible. If your theme is a Monday-level easy theme, crazy and obscure names are unwelcome. But if it’s a razor-tough Saturday themeless, a few tough words are okay.”

Crossword constructor Robin Stears suggested an additional step when choosing your entry words and filling the grid: “I check each word against a website called Crossword Tracker, which tracks crossword puzzle words and clues.

“If a word has never been used before, I hesitate to use it. The only exception to that rule is a fairly new word that I want to be the first to use—for a while, it seemed like every other puzzle contained ZZZQUIL, including one of mine.”

How to Make a Crossword: Cluing Advice

After constructing the grid, cluing is the most daunting task facing a constructor. Constructor Robin Stears readily confessed, “Writing the clues is the most time-consuming process of puzzle construction, especially for common words that appear in many puzzles. Crossword Compiler allows me to keep a database of words and clues, but I try not to use the same clue twice.”

Constructor and puzzle archivist David Steinberg: “When writing clues, it’s important to strike a balance between original clues and clues that exist in databases. For entries that appear frequently and/or have a limited number of cluing possibilities, such as ALAI (traditionally clued as [Jai ___]), I feel it’s best to go with a database clue. In the case of ALAI, almost all clever cluing possibilities, such as [Half-court game?], have been exhausted.

“Original clues for such an entry often end up feeling strained or wordy and/or rely on a less common usage of a word, which solvers generally don’t appreciate as much.”

Constructor Ian Livengood also stressed finding a balance between creativity and accessibility: “Keep you clues relatively short, especially if you’re creating puzzles for outlets with strict line counts. But don’t just use one-line clues for everything, since that will bore solvers. Try to toss in some fun trivia, wordplay, etc. that seems interesting to solvers.

“And, like filling the grid, make sure you clues are appropriate for the intended day of the week. [High line?] for ELEVATED TRAIN works well for a tough puzzle, but would only fluster new solvers in a Monday puzzle. [Above-the-street transportation] is easier and more welcome for beginners.”

Constructor Robin Stears reminds you to utilize the many resources available: “Personally, I use a number of websites to help me write clues: Wikipedia, Wolfram Alpha, The Free Dictionary, Crossword Tracker, Internet Movie Database, Reddit, and Google. In the old days, I used to spend hours in the reference section of the library, but nowadays, it’s much easier to search the Internet. There’s a wikia for almost everything.”

When it comes to determining the difficulty of a clue, constructor Doug Peterson suggests doing a bit of research: “My best advice is to solve lots and lots of puzzles of varying levels of difficulty. It won’t take long for you to get a feel for what types of clues are found in what types of puzzles. And it’s OK to have a few hard clues on a Monday or a Tuesday. Just make sure their answers don’t cross.”

Los Angeles Times Crossword Editor Rich Norris and assistant Patti Varol touched on how cluing can set a puzzle’s difficulty: “With the right grid, a talented, creative editor can transform an expert-level puzzle into one that any newbie can solve (and that an expert would still enjoy). Every editor has his or her own ‘familiarity test,’ which is the educated guess we make to determine if a clue or an entry will resonate with or be recognized by our solvers.

“It’s subjective, sure, but there are also pretty straightforward guidelines. If an entry is not in most major dictionaries and only gets 10K or so Google hits, well, that’s pretty obscure and probably shouldn’t be used at all. The editor needs to know the solving audience and needs to know how to balance current and older pop culture references -– much of what the Millennials find easy will completely baffle the Boomer solvers, and vice versa.”

They were also kind enough to offer an example of how cluing a given word can affect clue difficulty:

“Take the entry SMITH, for example. Will SMITH and Ozzie SMITH are arguably more famous than Patti SMITH, who is arguably more famous than Matt SMITH. Plain clues — [Actor Will], [Baseballer Ozzie], [Singer Patti], [Actor Matt] – tend to be hard. Ozzie is the exception in this example, because Ozzie is such an unusual name in baseball that even nonfans are likely to word-associate their way to the correct answer.

“What information is added to those semi-naked clues is key. Thus, [“Men In Black“ actor Will] is an easy clue for SMITH because “Men In Black” is a popular movie franchise and having the first name narrows down the potential answers. Compare [“Just Kids” memoirist Patti]. Even with that first name in the clue, it’s a tough clue — more solvers know Patti Smith as a singer than as a writer, and the title of her memoir doesn’t even hint at her singing career. For a nonfan, [Hall of famer shortstop Ozzie] is about the same difficulty as [Baseballer Ozzie], but, alas, it’s likely only a Doctor Who fan will recognize any clue for Matt SMITH.

“There’s Kate SMITH, and Bessie SMITH, and Agent SMITH of the Matrix movies. Each one resonates with a different solver. The easiest kind of clue for SMITH is, of course, the generic kind: [Common alias] or [Popular surname] or [Suffix with lock or gun]. And then there’s the fun, inferable kind: [Surname that comes from an occupational suffix].”