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14 Tricky Crossword Puzzle Clues That’ll Leave You Stumped

Ready for a challenge? These prime examples of wordplay and crossword lingo will give your brain a workout.

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town at the eighth mile of the Boston Marathon

“Town at the eighth mile of the Boston Marathon” (6 letters)

The answer to this tough crossword puzzle clue inspired a new principle for avid solvers, called “The Natick Principle,” so christened in honor of the answer, a small Beantown suburb. Rex Parker, of crossword blog fame, says that clues like this one, that have a proper noun as an answer that isn’t reasonably familiar to at least one-quarter of the solving public, should be crossed with “reasonably common words and phrases or very common names.” That way, you at least have a chance to figure out a clue you’ve never heard of because the cross clues are get-able.

Answer: NATICK

2 / 14
strips in a club

“Strips in a club” (5 letters)

Master crossword constructor Brendan Emmett Quigley explains how answers can stretch your mind to be more “elastic.” There are easier crossword puzzle clues for this answer, like “meat for breakfast,” but “strips in a club” makes your mind go to a totally different place. You’re probably not thinking club sandwich, which is where you need to be to get that answer.

Answer: BACON

3 / 14
la bamba actor morales

La Bamba actor Morales” (4 letters)

Lots of crossword puzzles feature this answer and it’s clued in a variety of ways, from tough to easy. It’s a word with lots of vowels and an “S,” so it provides a nice fill to a crossword grid. It’ll sometimes get clued with “Tony on NYPD Blue.” That clue provides another stylistic hint to let you know that you’re looking for a name, because of the use of the first name Tony in the clue.

Answer: ESAI

4 / 14
group of crows

“Group of crows” (6 letters)

The famed New York Times crossword puzzle gets harder as the week goes on, culminating with the toughest puzzle on Saturday. Monday and Saturday puzzles could contain the same answers, but Saturday’s clues will be way more challenging. Editors Will Shortz and Joel Fagliano typically don’t use clues that are grim or overly dark. The clue refers to this word’s less obvious meaning, a collective noun for crows—not having anything to do with premeditated killing. If you figured that out, you might be ready for these tricky detective riddles.

Answer: MURDER

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“Leaning column?” (9 letters)

When you see a crossword puzzle clue with a question mark, you can plan on having some fun to find the answer. Michael Sharp, the crossword expert behind the alias Rex Parker, notes the language used in crossword subculture, like “wordplay” (puns) and “crosswordese” (words frequent in puzzles, but not in real life). The “Leaning column?” clue is definitely wordplay. It has nothing to do with the Leaning Tower of Pisa like you might initially think. The question mark lets you know you need to think differently. The answer is OPED PIECE. Still confused? Read it as “op-ed,” a newspaper column expressing an opinion, or you know, a leaning. See if you can solve the first crossword puzzle ever published.


6 / 14

“Trilbies” (4 letters)

Some crossword aficionados consider “Trilbies,” clued back in 1987, one of the hardest crossword clues of all time. Part of the fun for solvers is figuring out obscure words and using knowledge of little-known trivia to find the answer. It might help you to know Trilby apparently refers to a character in an 1894 novel who had beautiful feet. It also turns up as a synonym for foot in 1911, and in a crossword puzzle dictionary in the 1970s. Talk about obscure!

Answer: FEET

7 / 14

“Pandora’s domain” (13 letters)

You can count on crossword puzzles to be filled with all kinds of trivia related to opera, classical music, literature, geography, and mythology. Crossworders possess an inner treasure trove of classical knowledge they can pull up to fill a grid. But you’ll also need a firm grasp on popular culture and the digital age. Because the answer here has nothing to do with the Greek myth of Pandora in Hesiod’s Works and Days.


8 / 14

“Peak south of Stromboli” (4 letters)

The answer to this clue shows up in crossword puzzles fairly regularly. Sometimes it has easy clues and sometimes they’re harder. If you ever get a clue looking for an Italian volcano, you can pretty much count on the answer being ETNA. It can also be clued as “Sicily smoker” (note the wordplay) or “Volcano of Sicily” (pretty straightforward). Watch out for clues like “Mount that’s a poker term when read backward.” Get it? If you can’t get enough of puzzles, take them with you these printable crossword puzzles.

Answer: ETNA

9 / 14
"Yep, perfectly clear"

“‘Yep, perfectly clear'” (7 letters)

You can rely on crossword puzzle answers appearing in the same form as their clues. In this case, the clue is surrounded by quotations, meaning it’s a spoken phrase. It’s also casual and slangy in the way it uses the word “yep.” So you can be sure that the answer will be a phrase that indicates the same thing and that contains informal language or slang.

Answer: I HEAR YA

10 / 14

“Room off an ambulatory” (4 letters)

The answer here is more crosswordese: It’s hard or easy to get depending on the difficulty of the clue. In this case, the word “ambulatory” (an adjective related to walking) is pretty obscure, unless you know the secondary meaning: A noun referring to a church aisle. If the clue is four letters and has something to do with a church or an altar, the answer is often (as it is in this case) APSE. See if you can solve the most challenging riddles ever.

Answer: APSE

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“[Boo-hoo!]” (5 letters)

You can bet you’re in for some mind-bending hijinks when a crossword clue is in brackets. Generally, that means that the clue refers to non-verbal communication or some other indirect reference, like in the example “[Over here!]” for PSST. However, there aren’t hard and fast rules for brackets in crossword puzzles. One of the aspects that makes tough clues so much fun for wordies is their nuanced wordplay that makes you think outside the box. Ready for some numbered fun now? Try these math riddles only the smartest will get right.

Answer: IM SAD

12 / 14

“Lead-in to ops” (3 letters)

Crossword puzzles will often have clues that refer to prefixes, suffixes, or words or terms that come before or after the answer. Clues will try to trip you up a little bit by using indirect phrases so you’re thrown off the trail. In this case, the clue wants you to think of three letters that could come before “ops.” The answer is SYS, as in sysops. That’s the term for admins on websites or message boards, short for systems operator. That’s probably the first thing that leaps to mind, right?

Answer: SYS

13 / 14

“Word repeated four times in the last line of Shakespeare’s ‘All the world’s a stage’ speech” (4 letters)

Brush up on all your Shakespeare factoids because they always turn up in crossword puzzles. You’ll need to know the plays for clues like “A Winter’s ___.” Fill in the blank with the answer TALE. Remember characters like OBERON, “King of the fairies in ‘A Midsummer Night’s Dream.'” It’s also a good idea to brush up on notable lines from the plays. In the case of this clue, you’ll need to be familiar with Act II, Scene VII of As You Like It. Jaques’ speech expounds on the seven ages of man, from “infant” through adulthood to “second childishness,” and finally reaches the line that contains the answer: “Sans teeth, sans eyes, sans taste, sans everything.” Sans is French for “without,” by the way.

Answer: SANS

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“Salmagundi” (4 letters)

Crossword puzzles often refer to the secondary meaning of terms to get at the answer. Salmagundi is an English salad comprised of a bunch of different ingredients like meat, anchovies, veggies, and an array of spices. It also refers to any mixture or hodgepodge. It’s also been used to clue the answer OLIO. “Olio” is one of those words that turns up fairly often in crosswords. It does refer to a Spanish stew, but also keep your eyes open for clues that refer to a mishmash, an assortment or collection, a mixed bag, a spicy stew, or a little bit of this and that. Can’t get enough of tricky word puzzles? These 15 will leave you stumped.

Answer: OLIO

Molly Pennington, PhD
Molly is a writer and collage artist with a PhD in film and cultural studies from the University of Pittsburgh. Her professional astrology services and artwork are available at Baroque Moon Astrology. She covers the zodiac, books, movies, TV and culture for Reader’s Digest, and loves to talk about all the ways we make meaning.