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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The New York Times Crossword, Accordion to Weird Al

 In February of 2017, The New York Times celebrated a landmark in the history of puzzles: the 75th anniversary of the NYT crossword.

And ever since, to commemorate that puzzly milestone, top constructors and Times favorites have been pairing up with celebrity fans and puzzle enthusiasts to co-construct puzzles for the Times!

This year, you might’ve encountered some of these collaborations, like news pundit Rachel Maddow’s March 2nd puzzle with constructor Joe DiPietro, or “How I Met Your Mother” star Josh Radner’s meditation-themed puzzler from January 31st with constructor Jeff Chen.

Over the last year, names as diverse as John Lithgow, Elayne Boosler, Joy Behar, Mike Selinker, Lisa Loeb, Neil deGrasse Tyson, and Bill Clinton have contributed their puzzly efforts to this marvelous project.

And yesterday, another famous wordsmith and master of punnery made his New York Times debut.

[Image courtesy of Instagram.]

Yes, the immortal “Weird Al” Yankovic teamed up with Puzzle Your Kids mastermind and friend of the blog Eric Berlin for a cheese-themed Wednesday outing that delighted fans and solvers alike.

Al has certainly been keeping busy lately, launching his Ridiculously Self-Indulgent, Ill-Advised Vanity Tour — his words, not mine; I loved the show I attended! — and working with Lin-Manuel Miranda to create The Hamilton Polka, an ambitious and hilarious take on the wildly successful musical.

The puzzle was Eric’s 40th Times puzzle, and Al’s first. Not only did the puzzle feature those signature cinematic cheese puns — like A FEW GOUDA MEN and THE PELICAN BRIE — but there was plenty of nerd culture featured in the fill and cluing.

Tom Lehrer and John Cleese were both name-dropped, as well as Legolas, Wile E. Coyote, WALL-E, Mr. Clean, and Bones from the original Star Trek.

Eric offered some insight into the puzzle’s creation while discussing the puzzle with Wordplay’s Deb Amlen:

My very first attempt at the grid included one of my favorites from his list, QUESOBLANCA. I was under the misapprehension that queso is not just the Spanish word for cheese but also a specific kind of cheese. Whoops, not quite. (This was entirely on me, I should note — Al, not knowing during his brainstorming that the end result would be restricted to specific cheeses, had several cheese-adjacent puns in his list, including FONDUE THE RIGHT THING and CHEESY RIDER.)

And appropriately enough, Al had a bit of fun promoting the puzzle on his Instagram, claiming, “If you’re REALLY good, you don’t NEED the clues!”

For the record, I needed the clues.


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Hashtag Game Fun with Puzzly Women!

Oh yes, it’s that time again! It’s time to unleash our puzzly and punny imaginations and engage in a bit of sparkling wordplay!

You may be familiar with the board game Schmovie, hashtag games on Twitter, or @midnight’s Hashtag Wars segment on Comedy Central.

For years now, we’ve been collaborating on puzzle-themed hashtag games with our pals at Penny Dell Puzzles, and this month’s hook was #PennyDellPuzzleWomen, mashing up Penny Dell puzzles with famous women both real and fictional!

Examples include: Lana Tossing and Turner, Adele Sunday Crosswords, and Madeleine Albright of Way.

So, without further ado, check out what the puzzlers at PuzzleNation and Penny Dell Puzzles came up with!


Selma Diamond Rings

Fill-Ins Diller

Katie Kakuroic

Mary Kay Places, Please

Cher-a-Letter

Priscyllacrostic Presley

The Maddow

Tie-Indira Gandhi

Midler’s Frame

Victoria’s Secret Words

In Black and Betty White

Gennifer Flowers Power

Stepping Sharon Stones

Classified Cheryl L-Adds

Marcia Crossroads

Ariana Grande Tour

Esther Rolle of the Dice

Tori Spellingdown

Sigourney Weaver Words

Maggie Wheelers

Debra Messing Vowels

Emily Observation Post

Tina Turnerabout

Diamond Ringrid Bergman

Word-a-Matilda

Kate In The Middleton

Evan Rachel Word Seek

Right of Fay Wray

Sylvia Plathboxes

Carly Simon Says

Shirley Temple Blackout

Chess-ica Simpson

Senator Barbara Mathboxer

Jenny “From the Blockletters” Lopez

Jigsaw Squares Eyre

Anne Bowl Gamelyn

Miss Piggybacks

Paris Hilton in Rhyme

Louisa May All Frame

Zsa Zsa Gaborderline

Twiggybacks

Marla Marbles

Mariah Carey-Overs

Kathleen Battleships

Dora the Exploraword

Mrs. Double-take-fire

Glinda the Group Values Witch

Diamond Li’l Rings

Major Margaret “Hot Blips” Houlihan

At Sixes and Seven of Nine

Elphababet Soup

Queen Ellery Elizabeth of Penny Dell

Mary-Kate and Ashley Double Trouble


There was also a submission that deserve its own section, as one of our intrepid puzzlers went above and beyond.

To the Cartoonist: Draw the Lynda Carter character Around the Block from the Double Trouble. We’ll Roll the Diana Prince into Wonder Woman and the Amazing Quote Amazon will take them down Brick by Brick.


And members of the PuzzleNation readership also got in on the fun!

On Facebook, Sandra Halbrook submitted the delightful entry Marcia Cross Sums!

Have you come up with any Penny Dell Puzzle Women entries of your own? Let us know! We’d love to see them!

Thanks for visiting PuzzleNation Blog today! Be sure to sign up for our newsletter to stay up-to-date on everything PuzzleNation!

You can also share your pictures with us on Instagram, friend us on Facebook, check us out on TwitterPinterest, and Tumblr, and explore the always-expanding library of PuzzleNation apps and games on our website!