5 Questions for Crossword Constructor and Wordplay Blogger Deb Amlen

Welcome to 5 Questions, our recurring interview series where we reach out to puzzle constructors, game designers, writers, filmmakers, musicians, artists, and puzzle enthusiasts from all walks of life!

It’s all about exploring the vast and intriguing puzzle community by talking to those who make puzzles and those who enjoy them! (Click here to check out previous editions of 5 Questions!)

And we’re excited to welcome Deb Amlen as our latest 5 Questions interviewee!

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[Deb in the center, flanked by her fellow Musketeers.]

Deb is a talented crossword constructor, but these days, it’s more likely you know her for her role as the head writer and senior editor of Wordplay, the crossword blog and educational/humor column associated with The New York Times crossword puzzle.

One of the most public faces associated with the crossword, Deb entertains and informs across both the blog and its associated Twitter account, as well as hosting a live-solving show on YouTube with fellow constructor Sam Ezersky and celebrity guests!

Deb 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 Deb Amlen

1. How did you get started with puzzles?

Word games like “Ghost” were always my favorite things to play when I was a child, but I didn’t really get into puzzles until I was a young adult. I watched my father solve the New York Times crossword when I was really young, but I didn’t start solving on my own until I bought myself a subscription to New York Magazine after college and discovered Maura Jacobson’s puzzles.

I started constructing crosswords when my own kids were young because, as a stay-at-home mom, I desperately needed a creative outlet that didn’t involve Pokémon or Elmo. I read everything I could about puzzle making and learned how to make crosswords from Nancy Salomon. Nancy has mentored hundreds of constructors to publication.

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2. As the flagbearer for crosswords in the public eye, The New York Times crossword is often the most scrutinized when it comes to cultural sensitivity regarding entries and clues, and more than once, that has depicted the Times puzzle in an unflattering light.

As a very public figure for the brand — not to mention the de facto social media gatekeeper — this puts you in the unenviable position of being between the audience and the editorial team. How do you handle these situations, and as an enthusiastic solver yourself, how do you think the Times is doing in this arena?

The crossword does get a lot of flack, doesn’t it? Honestly, some of it is warranted, some of it is not.

There is definitely a need to bring the flagship puzzle into the 21st century in terms of diversity and representation. Like most large companies, however, sometimes change happens slowly at The New York Times.

A lot of work is being done by the company and the puzzle editors behind the scenes, though, to increase diversity on their team and to be more aware of content that is inflammatory, and I think the recent puzzles reflect that. They have a ways to go, but the conversation is active and ongoing, and I’m very optimistic about the future of the crossword.

As far as social media goes, people tend to conflate “the Wordplay Twitter account” with “Everything The New York Times Does With Regard to Puzzles and Games.” So, since I run the Wordplay account and the puzzle editors are not really on social media, I tend to be the target of people’s complaints, which is hilarious because I’m just the columnist. Luckily, The Times has allowed me to expense a thick skin, so I’m doing OK. When I’m not, I take a break from social media, which I highly recommend and think everyone should do.

On the other hand, most people are well-wishers and are a lot of fun. They tweet their solving victories to me and I give them a gold medal emoji, which people really respond to. It’s very satisfying to be able to lift people up and encourage them, especially on social media, which can be very negative.

3. For the 75th anniversary of the New York Times crossword, constructors and celebrity guest puzzlers collaborated on numerous puzzles. Which celebrity constructors surprised you the most with their work, and who would you like to see as guest constructors in the future?

I’m not sure I was surprised by this, but I believe that Rachel Maddow’s crossword was one of the most popular, most downloaded puzzles we’ve ever had. Neil Patrick Harris’s puzzle had a very cool trick to it. And I can’t leave out the one I did with Natasha Lyonne, who was just brilliant to work with.

[Author’s note: When asked about her puzzle, Natasha said, “Working with Deb Amlen to create this puzzle has quite literally been a lifetime highlight for me.”]

4. What’s next for Deb Amlen?

Dinner, probably.

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

Enjoy yourself. This is not like sitting down to take the SAT; it’s a game. And games should be fun. Life is too short to sweat the crossword.


A huge thank you to Deb for her time. You can follow her on Twitter for updates on her puzzly and creative endeavors, and be sure to check out her work on the Wordplay blog and her very entertaining live-solving videos on YouTube. We can’t wait to see what she cooks up next.

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Puzzles… in… Space!

When you’re a puzzle enthusiast, you never know where your interest might take you, or what interesting and unexpected people you’ll encounter along the way. All sorts of folks enjoy puzzles, after all.

If you enjoy puzzles with trivia, you could bump into Who Wants to Be a Millionaire? winners or Jeopardy! champions like Ken Jennings. The New York Times has introduced us to several famous crossword enthusiasts. The British government is publishing puzzle books. Heck, actors Joel McHale and Neil Patrick Harris both included puzzles in their autobiographies!

Even astronauts are getting into the puzzly spirit!

Astronaut Tim Peake spent half a year in one of the most fascinating places in the solar system: the International Space Station. He was the first British astronaut to serve under the banner of the European Space Agency, and the first British astronaut to perform a spacewalk.

Upon returning to Earth, he turned his attention to more literary efforts, penning three books about space. The third, published last year in partnership with the European Space Agency, takes readers behind the scenes of the ESA screening process for astronauts.

Yes, puzzles are part of the screening process for the ESA.

Would you like to try your hand at solving some of them?

How did you do? Let us know in the comments section below! We’d love to hear from you

And if you’d like, you can find more of these puzzles in Peake’s delightful book The Astronaut Selection Test Book: Do You Have What it Takes for Space?

Do you have what it takes? I suspect that you do, fellow puzzler.


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Celebrity Constructors Galore!

[Bill Clinton enjoys a puzzle and a snack. Image courtesy of The New York Times.]

The New York Times Crossword celebrated 75 years of puzzles back in February, and ever since, they’ve been commemorating that puzzly milestone with a series of collaborations between established constructors and celebrity guests to create special monthly puzzles.

It started on February 15th, the 75th anniversary, with a collaboration by Patrick Blindauer and actor Jesse Eisenberg offering some food for thought with culinary wordplay.

On March 20th, astronomer and affable Pluto slayer Neil deGrasse Tyson joined Andrea Carla Michaels in creating a punny look at the stars.

Classical pianist Emanuel Ax teamed up with Brad Wilber to pen a music-minded puzzler on April 19th.

None other than former president Bill Clinton tried his hand at creating a crossword alongside judge and constructor Victor Fleming for the May 12th edition of the puzzle.

Tuesday, June 6th saw musician Lisa Loeb duet with crossword gentleman and friend of the blog Doug Peterson. Their theme involved concealing one-word #1 hit songs (including one of Loeb’s!) in larger phrases, leading to a Rihanna reference with UMBRELLAPOLICY, for instance.

And big names continue to appear.

Comedian and Tails of Joy pet advocate Elayne Boosler teamed up with Patrick Merrell for the July 12th puzzle, where they did modern day versions of classic films. For instance, Taxi Driver became UBERDRIVER and Holiday Inn became HOLIDAYAIRBNB. It was an excellent collab that made the most of Merrell’s gift of grid fill and Boosler’s wit and wordplay.

Clothing designer and television host Isaac Mizrahi joined forces with constructor David J. Kahn for the July 30th puzzle, employing crafty clues to put a spin on DIY construction phrases like “Cut and dried” and “On pins and needles.”

Tying a given puzzle’s theme to the guest constructor has been a recurring theme with the 75th anniversary puzzles, and the duo of Mizrahi/Kahn produced arguably the best examples thus far this year.

Most recently, constructor David Steinberg paired off with host, comedian, magician, and performer Neil Patrick Harris for the August 24th edition of the puzzle. Their magic-themed puzzle not only incorporated different parts of a standard magic show, but it concealed the name of a famous magician by hiding him among the down answers. (Or it would have, if he hadn’t escaped!)

Brilliant execution makes for a clever puzzle that Jeff Chen of XWordInfo declared one of his favorite puzzles of the year. (Of course, readers of the blog shouldn’t be surprised after solving the crossword Neil included in his autobiography.)

With more celebrity constructors still to come, including “a venerable TV journalist, a morning TV host, a six-time Emmy-winning actor, and a sitting U.S. senator, among others” (according to Will Shortz), I am definitely looking forward to seeing what other tricks these constructor/celeb duos have up their sleeves.


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Joel McHale Hides Puzzles Where You’d Least Expect!

Last year, I was surprised to stumble across a puzzle in the autobiography of comedian, actor, and magician Neil Patrick Harris, Choose Your Own Autobiography. It was a clever Neil-centric cryptic word-cross puzzle that rewarded attentive readers, since all of the answers were about events Neil discussed in the book.

So I guess I shouldn’t have been too surprised to again discover a puzzle in a celebrity autobiography. But this time around, comedian, host, and actor Joel McHale has upped the ante by offering three puzzles in his book Thanks for the Money: How to Use My Life Story to Become the Best Joel McHale You Can Be.

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Amidst hilarious anecdotes, bad advice for starting a career in Hollywood, and actual biographical facts, Joel includes a word-cross, a word search, and a matching game, all of which are about him!

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The matching game is arguably the toughest of the three, since you have to match the image of him to the name of the character he portrayed.

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The word-cross, though, is not far behind when it comes to difficulty, since the limited crossings offer fewer helpful letters to assist in solving. Not to mention that more straightforward clues like 1 Down — Second word in title of ninth chapter — are few and far between. More often, you encounter something like 14 Across — Anagram for synonym of puzzle.

Plus, there’s no clue at all for 33 Down, making the grid even tougher.

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Although I was able to solve most of the grid, some of the entries eluded me.

Still, I have to give style points to 29 Across: “Police Academy” star, if his name had one less “T” and he invented movable type for printing presses.

The word search, which is branded a “Wrod Jembul” (since Joel is dyslexic), is both the most creative and the most solvable of the three puzzles.

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In this puzzle, you’re given thirteen clues for various products Joel has done advertisements for, and you need to find them in the grid. Except every entry is jumbled up, complicating things greatly.

Although the puzzle is not perfect — FITBIT can be found in two ways, as can IHOP, and KLONDIKE BAR is the only entry spelled out for some reason — it’s great fun and a very fair solve.

Thanks for the Money is a very fun read, outrageous and engaging in equal measure. But finding a few puzzles inside? That’s the cherry on top.


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My Favorite Crosswords and Clues for 2016!

Tomorrow is the anniversary of the crossword — the one hundred and third, to be precise — and I thought I would celebrate the day by sharing some of my favorite crossword puzzles and clues from this year.

I solved more crosswords this year than any other year I can remember. From The New York Times, The LA Times, and The Washington Post to Peter Gordon‘s Fireball Newsflash Crosswords and our own Free Daily Puzzle on the Penny Dell Crosswords app, I tried to sample as many constructors and outlets as I could.

I want to start with Ben Tausig’s “Gender-Fluid” quantum puzzle from The New York Times in September. In a year that saw the Times called out several times for tone-deaf and insensitive cluing, to have a puzzle dedicated to the increasing awareness of other gender options was great.

And it certainly didn’t hurt that Ben’s grid was tightly constructed and each of the variable M or F entries worked well. (You can check out my full post on the puzzle here.)

“Eliminating the Competition” by Barany and Friends was another strong crossword with clever letterplay involved. The puzzle paid tribute to the American Crossword Puzzle Tournament by dropping the letters A, C, P, and T, respectively from the four theme entries in the grid.

Not only that, but there were no As, Cs, Ps, or Ts to be found anywhere else in the puzzle grid, which I thought was not only clever, but impressively challenging as a constructing gimmick. It was one of the most ambitious grids I saw all year. (You can check out my full post on the puzzle here.)

On the flip side — a puzzle that was more about the clues than the grid — there was the cryptic crossword from Neil Patrick Harris’s Choose Your Own Autobiography.

With clues like “Sounds like an assortment of taxis in which you were the MC (7)” (for CABARET) and “Costar a large, fake amount of money? (7)” (for FILLION), this puzzle not only rewarded attentive readers, but it severely taxed my (admittedly less-than-daunting) skills at unraveling cryptic clues. (You can check out my full post on the puzzle here.)

Oh, and on the topic of cryptic clues, I asked some constructors if there were any clues or puzzles that caught their eye this year, and David Kwong mentioned a doozy of a cryptic clue by master constructors Emily Cox and Henry Rathvon that he considered the most diabolical he’d ever seen.

The clue? “Emphatically, the key to making bozos boss? (9)”

The answer? SFORZANDO, which parses as “S for Z and O.”

That’s awesome. Doug Peterson did a variation on that in this year’s Lollapuzzoola tournament, “What Happened?”, which featured words or phrases where the letter H had been replaced with either a T or a Y. He revealed this with the entry “HISTORY” breaking down “H is T or Y.” I really dug this puzzle.

And speaking of Lollapuzzoola, I absolutely loved Francis Heaney‘s “Quote Boxes” puzzle from this year’s tournament. It was an 18×18 grid jam-packed with entries, and he used an interesting mechanic to fill the grid.

There were five 2×2 boxes shaded with different shapes, and each of the four cells in those 2×2 boxes contained a word from a famous four-word movie quote, allowing him to place longer entries in the grid. It was the highlight of Lollapuzzoola for me this year. Great stuff.

But before I get to the final crossword on my list, I’d like to run down some of my favorite crossword clues from this year.

  • “Island country that becomes a geometric solid if you change its last letter to an E” for CUBA (from Patrick Blindauer‘s Piece of Cake Crosswords. A super-long clue, but very fun.)
  • “Struggle with hopelessness?” for LISP (from Brendan Emmett Quigley)
  • “The Sky, Sun, and Stars play in it” for WNBA (from Peter Gordon)
  • “Answers, on ‘Jeopardy!'” for ASKS (I don’t recall where I saw this one. Let me know if you know, so I can correct this!)
  • “Some people do it for kicks” for KARATE (Again, no idea where I saw this one. Let me know if you know, so I can correct this!)
  • “Characters often found to be up in arms?” for YMCA (from Sam Trabucco’s Indie 500 puzzle)

And cluing tied into my final choice for favorite crossword of the year with Erik Agard and Joanne Sullivan’s puzzle “Do I Hear a Waltz?” from the Indie 500 tournament.

In this puzzle, the words ONE, TWO, and THREE were missing from sequential clues, providing a hidden one-two-three count for the puzzle’s titular waltz. For instance, 36-Across clued TRUMP as “Up,” 37-Across clued BIKINI as “Piece, say,” and 38-Across clued TITLES as “Peat makeup.” As you’d expect, those clues make much more sense when you add the hidden one-two-three: One-up = TRUMP; Two-piece, say = BIKINI; Threepeat makeup = TITLES.

Hiding the beat within the cluing was absolutely brilliant, and one of the highlights in crosswords for me this year.

Now I’m sure there were great clues or puzzles that I missed, since I’m hardly a prolific solver. Let me know which puzzles and clues from 2016 were your favorites! I’d love to hear from you!


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Neil Patrick Harris: Actor, Magician, Puzzler?

I’m a puzzle guy, so naturally I’m always on the lookout for new puzzles, whether it’s in the newspaper, the bookstore, the Internet, or anywhere else I happen to be browsing.

But sometimes, you stumble upon a puzzle in the unlikeliest of places. Like a celebrity’s autobiography.

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I recently got around to reading the autobiography of comedian, actor, magician, award-show host extraordinaire, and all-around champion of entertainment Neil Patrick Harris, and, as you’d expect from someone as creative as him, it was no ordinary affair. It’s written in the style of a Choose Your Own Adventure book, where you can make life decisions (as he did) and see where they lead!

Some lead to hilarious fake deaths, while others lead to genuine poignant moments from his life. We learn about his career, his discovery of magic, the peaks and valleys of his acting career, and his search for love, and it’s a great story. But he also includes messages from friends, drink recipes, and other hidden gems in the book, one of which was an unexpected cryptic crossword puzzle!

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Now, I’ve made no secret of the fact that I’m hardly the strongest cryptic solver around, but I couldn’t resist tackling a surprise Neil Patrick Harris-themed puzzle. (Thankfully, I was able to call in a friend who’s really good with cryptics for the clues that stumped me.)

To Neil’s credit, there are some very clever clues here, in addition to more traditional cryptic clues like “Let show (4)” for RENT and “Symmetries halved and reversed produce a ceremony (5)” for EMMYS. And, as you’d expect, most or all of them apply to events in his life, so you have to read the book to have any chance of solving this one.

Let’s look at a few of my favorites:

  • Sounds like an assortment of taxis in which you were the MC (7): An assortment of taxis is a CAB ARRAY, which sounds like CABARET, a show in which he played an emcee.
  • Costar a large, fake amount of money? (7): Actor Nathan FILLION costarred in Dr. Horrible’s Sing-Along Blog with Neil, and FILLION certainly sounds like a large, fake amount of money.
  • He was against you, and it sounds like he’s against everything (4): There’s a terrific story in the book where Neil is accosted by actor Scott CAAN, whose name sounds like CON.
  • Lothario! Unhinge 90 bras, boy!: This one takes a little work. “Unhinge” indicates this is an anagram clue, so if you anagram “ninety bras,” you get BARNEY STIN. Add “SON” as a synonym of “boy,” and you get BARNEY STINSON, the lothario he played in How I Met Your Mother.

Once you have your 24 answer words, it’s time to fill in the words Framework-style. Quite helpfully, there are several places in the grid where only one word fits, due to word length, which offers the solver several points of access.

However, only 23 of those words will fit in the grid, allowing for an alternate solve for the answers RENT and PENN. But there’s only one way to place the other answers so that the shaded squares spell out a ten-letter word that has a special meaning for clever and attentive readers, a code word Neil suggests as a sign of kinship with the reader.

I debated whether to share the word here, but I don’t want to deprive others of the joy of solving a surprisingly tough and enjoyable puzzle lurking inside an already fun read.


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