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How Many Of The 14 Trickiest Crossword Clues Can You Solve?

14 indie crossword editors share their favorites.

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1. It's less rich than the 1% [4 letters]

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"This is from a puzzle by Aimee Lucido run in 2015. It's the kind of clue/answer pair that probably could appear in a mainstream puzzle, but mostly because the indies made contemporary jokes more palatable. It fakes toward a newish language of class to mislead you, bringing the mind to Mitt Romney and Sheldon Adelson before alighting on a quart of dairy."

--Ben Tausig, American Values Club

2. Pussy riot? [6 letters]

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"I like clues like this because there’s double meanings in both halves of the clue – riot here is referring to a laugh riot, not civil disorder, and I doubt the Russian feminist group had kitties on the mind when they used 'Pussy' in their name."

--Andrew Ries, Aries Puzzles

3. Craving head? [5 letters]

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"A '?' in a crossword clue is the constructor's way of telling you they're messing with you. If you try to interpret the phrase 'craving head' literally, the most reasonable interpretation is fairly X-rated. (The correct answer is 5 letters long and begins with H, and I had many solvers tell me they tried HORNY before arriving at the correct answer). But the '?' tells you that at least one of the words in the clue has a non-obvious meaning. In this case, I used the word 'head' to mean 'front' -- that is, the front of the word 'craving.'"

-- Andy Kravis, Cruciverbalist at Law

4. Her porn star name might be Socks Pennsylvania [14 letters]

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"One method of creating your porn star name is by using your childhood pet followed by the street you grew up on. CHELSEA CLINTON had a cat named Socks while living in the White House (at 1600 Pennsylvania Avenue NW in Washington). I had wanted to make a whole theme out of porn star names, but there aren't enough well-known people whose pet names and street addresses are known. The only other one I came up with was Spot Mockingbird for Eddie Munster."

-- Peter Gordon, Fireball Crosswords

5. Journey accompanier, often [9 letters]

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"I'm a music geek, so any opportunity to write about music (whether it's in the clue or the answer) I'm going to take it. Because you capitalize the first letter in each clue, it can be fun to 'hide the capital,' so to speak. Since the band Journey is already capitalized, I can make you think I'm asking for something you might take on a trip rather than the band, because it's capitalized no matter what."

-- Brendan Emmett Quigley

6. Athletic supporter? [3 letters]

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"I like this clue so much because there are two ways to run with it. If you think about supporter meaning someone who supports, then the clue could be talking about a sports FAN, because that's three letters long. But you could also think of a supporter as something that physically holds something else up, then you might think of a golf TEE, which supports a ball. This clue is special to me because I wrote it for the first puzzle I ever got published."

-- Neville Fogarty

7. Means of getting high in Colorado? [4 letters]

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"As in the structural name for a ski lift. I was particularly pleased with this clue because it involved wordplay of an entire phrase: 'getting high in Colorado' is, um, definitely a thing by itself... and it usually doesn't reference skiing. As a constructor who is still in college, I'm always looking to give my puzzles a younger, racier feel, so coming across any clue or answer along these lines is a huge plus."

-- Sam Ezersky, The Grid Kid

8. With "down and shut the fuck up," take a chair [3 letters]

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"Sometimes in newspaper crosswords, you might see a clue like [1975 musical set in Oz, with "The"] for the answer WIZ, or [International Court of Justice site, with "The"] for the answer HAGUE. That's because nobody refers to the musical as just WIZ or the International Court site as just HAGUE, but THE WIZ and THE HAGUE. There's nothing flashy about the answer SIT, but I thought it would be funny to write a saucy clue that makes the answer blatantly obvious at the same time. It's sort of like in those SNL Celebrity Jeopardy sketches where the category basically spells it all out, like Foods That End In 'ambuger'."

--Evan Birnholz, Devil Cross

9. Michigan county I promise never to use in a crossword again [6 letters]

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"Sometimes you're stuck using a word that not many solvers are going to know, and you feel bad about it. So you can brazen it out by cluing straightforwardly, or you can take a contrite tone to let solvers know that you wish you didn't have to inflict this entry upon them. That's what I did here, and I've kept my promise in the intervening five years."

-- Matt Gaffney, Matt Gaffney's Weekly Crossword Contest

10. Turndown for Watt? [3 letters]

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"James Watt, the inventor who improved the steam engine, was Scottish and NAE is 'No' in Scottish. You can't not read this clue without that song getting stuck in your head."

-- Matt Jones, Jonesin'

11. U.S. national anthem [21 letters]

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"This was the marquee answer in a jumbo-sized puzzle. the theme was 'legends,' so every theme answer started with a word that could follow 'leg' (a 'leg'-end, if you will): WORK MIRACLES, LOCK HORNS, WARMER CLIMES, and so on. I'm proud of this clue/answer because I'm proud of my heritage, and also because, as I later found out, there's another 21-letter song title that fits the clue. Who knew?"

Erik Agard, Glutton For Pun

12. Winds up on a cliff? [6 letters]

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"This clue, from a May 2015 puzzle titled 'Mailing Addresses,' is a fave. For me, the cornerstone of puzzle-making is: writing twisty clues for simple, un-glitzy words. This clue hangs on the pronunciation of a single word. Solvers wrote in, saying they hated me . . . until they got to the 'aha.' Then all was forgiven. Until the next time, of course!"

Elizabeth C. Gorski, Crossword Nation

13. They pass gas... stations [6 letters]

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"There's been a lot of talk about everything Elon Musk has been doing and creating, so I wanted to make a pun on that. So, I went about trying to make a "hybrid" clue, which would use two definitions of gas. Maybe it's the inner teenager in me, but I love that I get to include this fart joke in my puzzle. Never gets old."

--Chris King, Chris Words

14. How to get a thong for a song? [4 letters]

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"There are certain words that show up in a crossword constructor's grid that just beg -- nay, demand -- to be clued in an insidiously clever way. It may be the subject matter of the word, the word may have a lot of synonyms, it may be easily adaptable to a clever bit of wordplay, or whatever other reason. ELOPE and RHYME are two of them... and LISP is another. I was brainstorming for some suitably giggleworthy pairs of 's'/'th' words (that represent a lisp) when I came across 'thong'/'song'. (Could this have been Sisqó's thought process too?)"

--Tim Croce, Club 72

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