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“A good puzzle makes the solver feel smart.”

David Kwong

A Brief History of the Crossword Puzzle

The first crossword puzzle was created by journalist Arthur Wynne and published in the New York World on Sunday, December 21, 1913. Other publications also began to publish similar puzzles and it had become a popular fad in the US by the 1920s.

Arthur lost interest in the job of crossword puzzle publication and handed responsibility over to Margaret Petherbridge, a secretary at the paper.

Initially, Margaret didn’t care much about the puzzle and often sent shoddy puzzles to print. Then in 1922 she had a change of heart and saw the puzzle as her chance to rise up in the organization and began to edit and publish only the best puzzles.

Petheridge also was the first to set standards for the puzzles such as dictionary words only and no lone letters that were part of only a single word.

Crosswords had grown in popularity in the few years after the first puzzle appeared but they became a full-fledged craze in 1924 when Simon & Schuster published the first book of crossword puzzles.

Even Walt Disney got in on the fad with his 1925 cartoon, Alice Solves the Puzzle.

By 1941, the New York Times was the last newspaper that didn’t have a crossword puzzle. But when the US entered WWII, the paper’s editors decided to get on board with crosswords and now have the gold standard of crossword puzzles.

As of 2023, there have been four full-time NY Times crossword puzzle editors and nearly 27,000 daily puzzles published. The current editor, Will Shortz, has edited nearly half of them! Here’s Will explaining the editing process that the puzzles go through prior to publication (a far cry from the first puzzles printed in New York World that were often full of errors as mentioned above). Also, you can see in the video that Mr. Shortz has an impressive reference library!!

The crossword puzzle celebrated its 100th birthday in 2013! Here’s a clip from CBS This Morning that year.

National Crossword Puzzle Day is celebrated every year on December 21!

Steps for Making a Crossword Puzzle

It’s a lot more complicated than you might think, but the basic steps for making a crossword puzzle are as follows.

  1. Choose your theme
  2. Create the grid
  3. Fill in the grid
  4. Write the clues

Easy-peasy, right?

Of those steps, the hardest is coming up with a theme. It needs to be interesting and novel and it must fit into the rotational symmetry rule.

(Check out the videos below under the “watch a puzzle being made” heading to see the rotational symmetry in action.)

interior of a book with chapter title arranged like a crossword puzzle grid
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I love the chapter headers inside Thinking Inside the Box! Very on theme for a book about crossword puzzles!

Rules for Crossword Puzzle Creation

Here are a few basic rules to follow when creating a crossword puzzle.

  • Never let two obscure words cross
  • Limit your crosswordese (words that are rarely found in real life such as ERNE and YSER)
  • All answers must be at least 3 letters long
  • Final grid must have rotational symmetry
  • It’s considered bad form to use too many black squares in your puzzle

Let’s take a side trip to the dictionary, shall we? What do those crosswordese words mean anyway?

ERNE: (noun, pronounced like urn) eagle, particularly a long-winged sea eagle. Bonus trivia – a bald eagle is a sea eagle!

YSER: (proper noun, pronounced with a long e then a z sound then air, Ezair) a river in France and Belgium that flows to the North Sea

Watch a Puzzle Being Made

First, for a general overview of how a puzzle is made and how the rules mentioned above look in action, check out this video from Slate’s Mike Vuolo, an occasional crossword writer for the New York Times and others, as he walks us through the process of making a puzzle.

You can also watch New York Times crossword puzzle constructor (also known as a cruciverbalist), David Kwong, show how he makes a crossword puzzle.

Now you’re ready – head on over to the New York Times website for the Crossword Constructor Resource Guide and get started on making your first puzzle!

Crosswords Together

Some people like to do puzzles alone and some people enjoy working together. Some NEVER look up answers while others don’t mind finding a tricky answer online.

For me, actually doing a crossword puzzle would have to be collaborative. First of all, I’m not that great at crossword puzzles. And second, I’m not competitive. At all. Teamwork all the way!! But how do you do it collaboratively when people are distant from each other?

wooden tiles spell working together in a crossword fashion
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Fill out your own grid but compare answers

You can each have your own copy of the puzzle but check in with each other for hints on words you aren’t sure about.

Do a puzzle together online

In 2020, The New Yorker added a partner option to its online crossword puzzle. Now you and one friend can solve a single puzzle together, on the same grid.

But what if you want to solve with a larger group of friends? Thanks to the r/crossword subreddit I found this website where you can do just that. DownForAcross is a website where you can choose from uploaded puzzles, invite friends with a link, and solve together.

screen capture of a crossword puzzle grid found on Down for a Cross website
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This is how far I got on my own after 15 minutes and I did not finish the puzzle. Too hard! Next time I’ll have to invite my friends to help!

Join a crossword competition!

Are you the best crossword puzzle solver you know? Well then maybe you’ll want to sign up for a crossword puzzle competition!

American Crossword Puzzle Tournament

The American Crossword Puzzle Tournament is held annually in late winter/early spring in New England. The first thirty years were in Stamford, Connecticut, but the tournament became very popular after the Wordplay documentary and the contest was moved to Brooklyn, New York to a larger venue.

The tournament was founded in 1978 by Will Shortz, the current New York Times crossword editor. To see the tournament in action, search the tournament on YouTube. There are several final rounds shown in full length. Those videos aren’t as long as you might think though – those crossword puzzlers are FAST!

Other Crossword Puzzle Competitions

The American Crossword Puzzle tournament is the largest by far but there are a couple of other competitions out there.

  • Lollapuzzola – the second largest tournament, founded in 2008, held on a Saturday in August
  • United States Open – also created by Will Shortz, ran only from 1982-1986, sponsored by Games Magazine
close up of crossword puzzle grid and pencil
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Crossword Puzzles in Movies, Books, and Podcasts!

Crossword Puzzles in the Movies (and television)


The Wordplay documentary came out in 2006 and features the current New York Times crossword puzzle editor, Will Shortz, as well as the 2005 American Crossword Puzzle Tournament. Wordplay was the best-reviewed documentary film of the year according to Rotten Tomatoes. Even The Simpsons had an episode inspired by this documentary – Homer and Lisa Exchange Cross Words.

Here’s the trailer for Wordplay

The theme song for Wordplay is Every Word written by Gary Louris. Here it is if you’d like to listen-

All About Steve

All About Steve is a 2009 romantic comedy starring Sandra Bullock as an eccentric crossword puzzle constructor who falls in love with her blind date, played by Bradley Cooper. Not a runaway hit but a fun movie! Here’s the trailer for All About Steve.

Crossword Mysteries

The Hallmark Movies and Mysteries channel has a short (5 episode) series called Crossword Mysteries. In this show, Tess (Lacy Chabert), a Sentinel crossword editor, helps Detective Logan (Brennan Elliott) solve murder mysteries.

Check out the preview for Episode 4 – Terminal Descent then head on over to get your Hallmark and crosswords fix at the same time!

Crossword Puzzles in Books

Thinking Inside the Box

Thinking Inside the Box: Adventures with Crosswords and the Puzzling People Who Can’t Live Without Them is written by Adrienne Raphel. Adrienne goes through the history of crossword puzzles, sharing fun bits of trivia along the way. She then goes the process of learning how to make a puzzle and even creates her own to submit to the New York Times.

Despite my decided lack of enthusiasm for completing the puzzles myself (really, why do I dislike them so much? Is my ego really so fragile that I can’t stand not being able to do them well?), I really enjoyed this journey through the life of crossword puzzles and all the nuance within.

Puzzle Lady Cozy Mystery Series

Since 2000, Parnell Hall has been writing the Puzzle Lady cozy mystery series. The main character is Miss Cora Felton, an eccentric old lady with a syndicated puzzle column. It looks like there may be a crossword puzzle included with each book as well to go along with the story. I haven’t read this book yet but I do love a good cozy mystery!

The Marlow Murder Club

The Marlow Murder Club by Robert Thorogood is a fun series with a crossword puzzle constructor as the main character. Judith Potts is a retired lady who swims naked in the Thames River and sets crossword puzzles for the newspaper to keep herself busy. She overhears a murder and becomes involved in solving it herself when local police won’t believe her claims.

There are two books published in the series with a third book due out soon.

Just announced – PBS will be making a television series based on the Marlow Murder Club books!

Crossword Mysteries

Another cozy mystery series featuring crossword puzzles is the Crossword Mysteries by Nero Blanc. Book 1 is The Crossword Murder.

Book titled Thinking Inside the Box is shown along with a New York Times newspaper and crossword puzzles
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Crossword Puzzle Podcasts

At first it might seem odd to have an audio format for a visual, written puzzle but don’t worry – it works!

Stuff You Should Know

Stuff You Should Know is always my go-to podcast for good general information about a topic. Josh and Chuck have two crossword episodes – a mini and a full-length episode.

Jean and Mike Do the New York Times Crossword

Now you know the history… you can listen to episodes of Jean and Mike Do the New York Times Crossword to get insight about any of the daily puzzles. They talk about how they did on that day’s puzzle, what they thought of it overall, and what they learned. Here’s a sample episode:

Songs About Crossword Puzzles

Not surprisingly, there aren’t many songs about crossword puzzles. But this song from 1925 – Cross-word Mamma, You Puzzle Me (But Papa’s Gonna Figure You Out) – was a big hit during the initial crossword craze!

You can listen to the song here:

Another more recent song about crosswords is Crossword Puzzle by Richard Maltby, Jr. and David Shire. It was written for the musical revue show titled Starting Here, Starting Now, in the 1970s.

Here’s a performance of the song by Jennie McGuiness who sang it as part of her senior recital.

Artificial Intelligence vs Crossword Puzzles

It seems that AI is all the rage these days and it has entered the world of crossword puzzles as well. “Dr. Fill” is a computer program created by Matthew Ginsberg that uses a database of words to solve crossword puzzles.

According to Ginsberg, “Dr. Fill solves puzzles by finding similarities between the clues in the puzzle and the clues it knows about. Then it just tries to cram in the words in a way that satisfies the fundamental crossword requirement that if two words cross they cross at the same letter. It doesn’t know what it’s doing; it just sort of stumbles around. But it gets pretty good results.”

So the computer is just like me – it doesn’t really know what it’s doing. Its advantage is the speed at which it can try various word combinations until it finds one that works.

Another fun fact that I love about this story is the reason behind the creation of Dr. Fill. Matthew Ginsberg claims to be one of the worst crossword puzzle solvers around. After being so frustrated at his inability to solve the puzzles, he used his computer science skills to make the program.

(I am also terrible at solving puzzles but not a computer scientist. haha)

Dr. Fill entered the American Crossword Puzzle Competition in 2012 and placed 141st out of 160. After several years of improvements to the program, it won the competition for the first time in 2021. Fortunately, all prize money goes to the actual humans competing, not computers.

Watch Dr. Fill in Action

Dr. Fill takes on the July 15, 2016, New York Times crossword puzzle. It’s a pretty short video. Did we mention? Dr. Fill is FAST!

More Word Fun

For more fun word history, read all about Peter Roget and his thesaurus.

The Right Word is a children's biography of Peter Roget. It tells of his struggles with mental illness and how he was able to use his book of words and lists to keep despair at bay. His Thesaurus and many scientific writings continue to serve the world today.
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The Right Word is a children’s biography of Peter Roget. It tells of his struggles with mental illness and how he was able to use his book of words and lists to keep despair at bay. His Thesaurus and many scientific writings continue to serve the world today.

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  1. That was really interesting and very thorough. That must’ve taken you forever to do!

    1. I definitely spent a lot of time on this which is funny to me as someone who doesn’t even do crossword puzzles. Haha! It was so interesting though to dig in to the history and the puzzle-making process.

  2. My father was an avid crossword player. I used to buy the “easy “ puzzle books from the grocery store and could finish a game in about five minutes but now they seem to be filled with other types of games. Now I play the NYTIMES daily mini puzzle and Wordle. Thank you for sharing this info with us!

    1. I like to buy the EASY puzzle books too. Easy seems to be the right level for me for any type of puzzle. One of my favorites was the logic puzzles with the grid.

  3. What a fun and engaging piece, Sheila! I definitely appreciate crossword puzzles and how they’re created even more. I also enjoyed the supporting videos. “The Marlow Murder Club” intrigues me and it’s cool to think they’re going to make a televised version of the story. I should read it first!

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