When I vacationed in the UK, I tried out their cryptic and could only produce a few words. I could tell from the clue structure how the component parts would assemble the answers, but realized I didn’t know enough about UK culture to get them.
I’ll often read (and sometimes contribute to) some of the reader’s comments to NY Times crosswords. Some folks aren’t happy with the evolution toward new slang, hip-hop references, etc. – while others aren’t happy with the retention of old-school knowledge stuff. I think the overall balance is fine. Plenty of cleverness, in some of the clues of any puzzle, as well as in special innovations in certain ones (typically Thursdays).
Luckily, that’s when my collection begins. I picked it out and indeed, there you are! I’m currently working on the (old) September issue I recently got, but I’ll take (another) look at the article sometime.
I really think puzzle constructers are getting lazy, because with texting acronyms, hip-hop and rap, and foreign languages you’ve got every possible combination of three to five letter words covered.
I know there is a strong Hispanic and Jewish culture in the U.S., but the NYT crossword goes overboard with una, habla, shofar, aleph, etc etc
The link in the post you quoted is a great source, unless you dislike the extra gimmicks in Cox and Rathvon’s puzzles.
I wonder if we’ve crossed paths in the comments!
re: the general question, though: it’s worth noting that the NYT has also made an effort to showcase newer, younger, and more diverse crossword creators, which has implicitly shifted the nature of the clues. For an interesting example of this, you can see LEIA’s evolution from “sci-fi princess” to “sci-fi general”/"leader of the resistance” in the 2010s. But in the general sense, I think that if you play crosswords, they get easier, because crosswords are 20% knowing the answer to 80% knowing the constructor.
I consider it a bad week if the Monday or Tuesday puzzles take more than 4 minutes. This is not because I am smart. I am dumb as a post. It’s because I only do the NYT crossword, and I have solved enough of them that when I see “woodwind instrument related to a Roman tibia” I know the answer is “oboe” purely from “woodwind instrument” even with no idea of what a Roman or a tibia or a relation is.
If you trained a parrot that every instrument is an OBOE, every bladed weapon is an EPEE, every cookie is an OREO, every fairy-tale creature is an OGRE, every television show is SNL , every plant is ALOE, every miner extracts ORE from a LODE, the only two musicians are ONO or ENO, and the only website is ETSY, that parrot would start the NYT crossword at an advantage better than a Harvard education every time. Even better if it came from the Hawai’ian locale of Mauna __a.
If you look back in the archives, older puzzles are going to appear more difficult because you will lack the context both of the surrounding popular culture, and of the implicit rules of the constructor. If you plopped that parrot down in the 90s and didn’t also tell them that the only cooking ingredient is OLEO and the only lake is ERIE, they would be at a disadvantage. That’s not because older crosswords required better knowledge of geography and cooking 
That said, there’s also some Baader-Meinhof phenomena at play, I think (I am also guilty of this), because i.e.
The NYT has used HABLA as an answer 7 times in the last decade, all but once clued as “(Se) ____ español?” SHOFAR(s) has appeared only once—yesterday, presumably why you mentioned it. ALEPH has appeared 14 times. UNA , generally clued as “__ article,” where __ is Spanish, Italian, Andean, Andalusian, etc, has appeared 37 times , more than the 33 examples of UNE but less than the 40 of EIN (either “German article” or “Ich bin ___ Berliner”).
(That said, ETE, ETRE, TETE, and AMI(E) by themselves have appeared more than 300 times in the last decade, so I think if the NYT wants you to know any language, it’s French)
Roz Chast once gave a speech at a crossword tournament: “I have to tell you that I was not the first choice for being the presenter. ALAN ALDA was, but he was on vacation, climbing an ARETE in the URAL mountains. They tried to get EERO Saarinen, but he had fallen on his EPEE. Luckily, his AMAH had some ALOE in her ETUI…..”
Crosswords (at least the NYT) have their own very specific vocabulary that has to be learned, almost a private language just in terms of frequency and likelihood of certain words. Any three-letter fish is an EEL, any sweet treat (or black-and-white thing) is an OREO, anything having to do with a mine is ORE, etc. When you know what to expect in the fill, it can turn into mostly gimmes, but compared to a practiced solver any person of the same intelligence and cultural background won’t be ready for all the buzzwords till they’ve been solving for a bit.
If only Thomas Meehan were still alive and constructing puzzles. He wrote the fabulous “Yma Dream.”
In this dream, like so many real life ones, the opening is simple yet totally unlikely. Meehan, a nobody writer living in a small Greenwich Village apartment, throws a cocktail party for unknown guests. The first to arrive is Peruvian singer Yma Sumac. She is followed by actress Ava Gardner. Meehan introduces them. “Ava, Yma.” Then the deluge. They are followed by Israeli Foreign Minister Abba Eban; Oona O’Neil, the wife of Charlie Chaplin; and Italian playwright Ugo Betti. Actresses Ona Munson and Ida Lupino show up together; Abba Eban glares at the playboy Aga Khan; novelists Ira Wolfert and Ilya Ehrenberg bookend one another; actress Eva Gabor swans in; and actress Uta Hagen completes the crowd overwhelming Meehan’s tiny living room. As each is laboriously introduced, the mood crackles as the apparent mockery darkens the event.
“O.K., O.K.,” I snap crossly. “Uta, Yma; Uta, Ava; Uta, Oona; Uta, Ona; Uta, Ida; Uta, Ugo; Uta, Abba; Uta, Ilya; Uta, Ira; Uta, Aga; Uta, Eva.”
The published at least one book of cryptics back a while ago, which I did, but that was before the WSJ puzzles. So, thanks,
Great post.
Even though I think all of that is true, puzzles can still be fun. I thought yesterday’s (9/18/25) was quite well done. I often just ignore the themes and work the crosses until all is revealed. Yesterday’s was just tough enough (both the theme and the cluing) that I had stop and work it all out. I sorely wish a Sunday puzzle could be at least as challenging. It’s been ages.
There should be the Upside-Down Crosswords. Kinda like the real Upside-Down in “Stranger Things”.
Where a deep knowledge of Curling’s most revered masters (that’d be Oskar Eriksson of Sweden, of course) will save the day, as will the names of the inventors of MobileWare, which is a type of Styrofoam (Ray McIntire). The easy questions will be related to the origins of Velcro™ (George de Mestral) and so on.
Those of us NOT adept at the NYT crossword await this new challenge.