10 Unique Puzzles With Answers

When you think of crossword puzzles, you probably think of lazy Sunday mornings, hot coffee, and pondering clues as you gaze out a rainy window. On the other hand, you might associate crossword puzzles with nursing homes, hospital wards, and getting frustrated quickly and giving up once all the easy answers are filled in.

However, you may not remember some of the most famous and sometimes controversial crossword puzzles that got the attention of the American public, coverage from the media, and even ended up in a documentary. Crossword puzzles can be great fun, so here are 10 of the most unique crossword puzzles with their answers.


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November 5th, 1996, The New York Times Puzzle

This puzzle is known throughout the United States as one of, if not the most famous crossword puzzle out there. The creativity and ingenuity of this puzzle caused quite an uproar among Americans as multiple questions could have several different answers, all based on the actual results of the 1996 United States presidential election.

The 1996 presidential election was an incredibly close race between Bob Dole and Bill Clinton. One of the questions asked for the headline of the next day’s newspaper, knowing that the answer would be “BobDoleElected” or “ClintonElected,” depending on the actual outcome of the race. This created quite a commotion at the New York Times.

People did not know that the creator of this puzzle, Jeremiah Farrell, had purposefully designed this crossword to allow for either answer to be correct. He obviously could not predict the future, but with questions such as, “Black Halloween animal,” the answer could be either “BAT” or “CAT.” The rest of the questions were similarly ambiguous.

The answer key was based on the actual events of the presidential election, making this crossword puzzle one of the most impressive and interesting puzzles to date. This crossword was the subject of a lot of media attention, can be found in the book, “The Crossword Obsession,” and was even featured in a documentary entitled “Word Play.” 

September 1, 2016, The New York Times Puzzle

Print journalism is an interesting thing in and of itself. It is somehow an entity that can cause upset and change social views while at the same time being used to wrap the next day’s fish. This puzzle from 2016 by Ben Tausig changed NYT history and was a huge win for members of the LGBTQ+ community.

This puzzle was another Schrödinger puzzle like the famous 1996 puzzle. However, this crossword may have been even more impressive in how it focused on the ambivalence caused between shifting just two letters and yet ended up speaking volumes. The two letters were “M” and “F,” symbolizing the two original genders, male and female.

Four of the answers could have been answered one of two ways, each based on switching those two letters. For example, “Part of a house” could be answered as “ROOF” or “ROOM.” The theme of this crossword which ties everything together can be found right in the middle of the puzzle, “GENDERFLUID.”

This was a first for the New York Times as this word, nor the word “QUEER” in the LGBTQ+ sense, had never previously been included in a crossword. The answer key shows four different questions that could be answered with either a word starting with an “M” or an “F,” which rather elegantly displayed the ambiguity of such a concept.

November 23, 2009, The New York Times Puzzle

Most Americans tend to associate crosswords with those of an older generation, after all, few young people get their daily news in print. Notwithstanding, there are a few impressive youths that enjoy the wordplay of a crossword puzzle, and even more impressive are the youngsters that enjoy creating crossword puzzles. 

At the tender age of 14 years, Ben Pall became the youngest crossword puzzle writer to be published in the New York Times during the editing era of William Shortz, and held the record, at least until another young man replaced him eight years later. A few other puzzle creators have been published at a very young age, such as:

  • Michael W. Miller- age 14 years, 0 months
  • Daniel Larsen- age 13 years, 4 months
  • Arthur Bennett- age 13, 10 months

The 2009 crossword is Ben’s first published puzzle, but he was published three more times for puzzles he created. The completed puzzle is cute and the questions are not too difficult, although the crossword becomes infinitely more impressive when you consider how young the creator was when the whole thing was published.

That being said, solving or creating a crossword puzzle is not necessarily a game for any one age group. In fact, there have been over 50 teenage crossword puzzle creators that have been published in the New York Times. Many of them have been published multiple times. With a little dedication and some time, you could probably make one too.

December 18, 2016, The New York Times SUPER MEGA Puzzle

This puzzle is the first of an annual New York Times tradition of something they like to call the “SUPER MEGA Crossword Puzzle.” This puzzle is an absolute monster, with 728 clues, it is sure to take even the most adept puzzlers several days to solve. The puzzle has to, not only span, but fill two pages in order to fit all of its glory.

Sunday puzzles are known to be the most difficult as most people will have more time to kill and finish the puzzle. This particular puzzle, although released on a Sunday, was designed to be more or less the difficulty of a Tuesday or Wednesday so that even with the hundreds upon hundreds of clues to solve, the crossword would still be finishable. 

Since 2016, the NYT has continued to produce one of these massive crosswords every year around the holidays. For many people and their families, it has become a sort of crossword tradition; a good excuse to get together, eat some Christmas cookies, and be baffled by how overwhelming the sheer size of this puzzle is.

As long as you submit your completed and correct crossword by the set date, you have a chance to win up to $1000. While there can only be one winner, the ability to correctly finish this massive puzzle should be enough of a reward. For 5-25 runners-up, they also win a consolation prize in the form of, you guessed it, more crosswords from NYT.

December 21, 1913, The New York World Puzzle

This puzzle was actually the first printed crossword in existence. This crossword was created by Arthur Wynne, who is also known as the father of this type of word puzzle. The style and layout of this particular original are pretty simple, especially when compared to some of the more complicated examples of puzzles listed above.

Crossword puzzles actually started in England in children’s books as word squares. Each line and column in the word square would read as different words. When the crossword as we know it crossed the pond with Wynne, it became a new thing in and of itself. In fact, Wynne’s puzzle was shaped differently than the version in modern papers.

Furthermore, his puzzle did not have any squares blacked out and instead was designed to be played without any blacked-out sections at all, except for the smaller diamond shape that was omitted in the middle. The ending result is more of a diamond-shaped frame rather than the square we are usually used to seeing today.

It is interesting to note how the original puzzles were so simple. Wynne’s version can not even touch the current New York Times SUPER MEGA crossword that comes out annually. The finished puzzle proves just how easy the original prototypes were. These first crossword puzzles were pretty easy to solve, with questions such as: 

  • A boy- LAD
  • What artists learn to do- DRAW
  • Found on the beach- SAND

December 26, 1987, The New York Times Puzzle

This puzzle is generally known to be one of the hardest Saturday crossword puzzles ever. It is worth mentioning that Saturday and Sunday puzzles are already supposed to be more difficult. Taking even the best and most seasoned crossword enthusiasts days to solve, this puzzle has a few clues with answers that do not seem to make sense.

For example, the most difficult clue is “Trilbies.” When you look up trilby in the dictionary, it is a noun meaning a fancy type of hat, similar to a fedora but with a shorter brim. However, the actual word for this clue in the NYT puzzle is FEET. It does not seem to make sense, even to several modern crossword creators and editors from the NYT.

It is difficult to see the connection between an article of clothing that is worn at the top of your body and the part of your body that is on the opposite end. Crosswords that are impossible to solve because of little-known words are just plain annoying! Another difficult clue is “Great Wall Town.” The answer, “LINYU” is not even found on an atlas.

With William F. Shortz at the helm of the crossword department, more modern crossword puzzles published in the New York Times today are based on the cleverness and difficulty of the clue, rather than the obscurity of the word. Thank goodness for that.

December 15, 2019, The New York Times SUPER MEGA Puzzle

The third year of this fun, annual mega crossword put out by the New York Times had an especially cute and unique theme to it. Just in time for the holidays, the 700+ clue puzzle asked the question to win, in addition to sending in your puzzle completed correctly, “Which of Santa’s reindeer is the only one missing from this puzzle’s clues?”

Families got together from all over the world to win the prize money. Some families even united across Google spreadsheets so they would not have to be in the same physical location to solve this monster of a crossword puzzle. Several people have said that this annual mondo crossword has become like a family tradition for them.

The answer to which of Santa’s reindeer was missing from the clue list ended up being Prancer. The clues to this list were really clever, asking questions like “Dancer Fred or Adele” meaning ASTAIRE, or “‘Blitzen’ is the German word for it” meaning LIGHTENING. 

Many people wrote in with very positive comments about the crossword as they sent in their completed puzzle. It is a very cool thing to think that one thing could bring so many across the country together, especially as people worked on this crossword with their:

  • Roommates
  • Family members
  • Friends

February 1, 2021, The New York Times Puzzle

This day marked the first puzzle created by the youngest female teenager printed in the New York Times, Soleil Saint-Cyr. This puzzle was printed on a Monday, so easily one of the least difficult of the week, but her theme of African-American culture made this debut puzzle worth a second look.

One of her questions featured a quote by Malcome X,” Early in life, I had learned that if you want something, you had better ___ some noise.” The answer to this clue was MAKE, but the actual meaning behind this quote spoke volumes more than this. The entire week’s crosswords were created solely by African-American writers.

Saint-Cyr, only 17 years of age when this was featured, also highlighted some 2020 history as America continued to process what has become known as “unprecedented times.” Another clue asked, “One on the front lines during a crisis,” meaning ESSENTIAL/WORKER. 

Claiming her spot as the youngest, Soleil Saint-Cyr is only one of eight young women that submitted a crossword in their teens that ended up being printed. A feat in and of itself, the next three youngest female teens were:

  • Kelsey Boes- age 18 years, 10 months
  • Clara Williamson- age 19 years, 2 months
  • Nina Sloan- age 19 years, 5 months

December 12, 1948, The New York Times Puzzle

The first teenager to be published for their crossword puzzle creation, at least in the New York Times, was Harold P. Furth. Many young people that were first published in their teenage years went on to create and submit even more crosswords as they grew older, but for whatever reason, Furth was only published that one time in the late 40s.

He may not have been the youngest puzzle creator to have been published in the New York Times, but certainly, for his age, his work was well above par. There have been suggestions that some teenage crossword creators had help from their parents, which makes more sense when you consider the youngest were only 13 and 14 years of age.

However, being only 18 years and 10 months old at the time his crossword ended up in print, you would never have guessed the young age of the creator, as the subject matter of the clues is quite developed. Perhaps Furth was taking a college history course at the time of his submission as the clue material seems to stem from:

  • Greek mythology
  • Arthurian legends
  • Middle Age history
  • Christian canon

The entirety of the puzzle contains over 160 clues, making this crossword seem like a more experienced creator must have had a hand in it. Because the crossword was so successful and debuted on a Sunday no less, it is curious that Furth did not go on to create, submit, and be published more in the New York Times.

February 20, 2012, The New York Times Puzzle

If Saturday and Sunday crossword puzzles are known to be some of the most difficult, Monday puzzles are some of the easiest. This puzzle from 2012 is said to be perfect for beginners, or at least that is what William Shortz, the current crossword editor says. 

The theme features subjects related to President’s Day, such as legal and political jargon. However, this puzzle also includes its fair share of pop culture references, with clues such as:

  • Steve, of The Office- CARELL
  • Big Supermarket Chain- KROGER
  • Silent Performer- MIME

The majority of the puzzle, however, includes clues alluding to what Nancy Pelosi was the first ever to be called in regards to her title in Congress, “MADAME/SPEAKER.” The theme of this puzzle being political in nature was perfectly planned, as February 20th was literally President’s Day in the United States.

If you managed to pass high school political science, or have a bit of a clue about what is going on in the world of politics today, this crossword should be a breeze. If you are wanting to get into crosswords, but never being able to finish one discourages you too much, this simple puzzle is a great place to start.


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