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.
“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. Check out these brain games that’ll boost your brainpower.
“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. For some more brain teasers that’ll test your elastic thinking, try to find the missing words in these puzzles.
“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.
“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.
“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.
Answer: OPED PIECE
“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!
“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.
Answer: INTERNET RADIO
“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.
“‘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
“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.