Of all the mundane things I do that seem to impress people, solving a crossword puzzle with a pen is among the most satisfying. Does it bother me when I get a word wrong, and have to scribble out a whole line of squares before writing in the correct letters in tiny, cramped corners? Not so much! Does it bother me when I can’t quite finish the puzzle without having to look something up? A bit more, if we’re being honest. But even if I don’t possess the truly universal knowledge required for immaculate puzzle solving, I won’t put down my pen.

(I don’t use this pen, though, because the ink would run right through the page. I use this pen for writing things, on much higher-quality paper.)
A dozen years ago, I received a copy of a puzzle anthology: Will’s Best, Celebrating the 20th Anniversary of The New York Times Puzzlemaster. Will of course is Will Shortz, who has now been editing the Times’ puzzles for going on 32 years (that’s not a nice round number, but this isn’t really about him). I am, to my chagrin, still working on it, having mostly solved its collected puzzles in short bursts, and then put the book down again while other concerns occupied my attention. The idea that they might run out one day seems both tragic and impossible to imagine. Nevertheless, I have reached a milestone of sorts: before me sits puzzle 261 of 400, the first one to be designated with a three star difficulty rating.
I have grown as a puzzle solver since I got this book. The one-stars used to be embarrassingly hard to finish, but by the time I got to the end of that section they were a breeze. I’ve aced some of the two-stars, though I usually find myself in a corner with one or two squares unfilled before having to resort to looking up an answer. The secret to solving a puzzle is not just about knowing what things are and what words mean (although that is an essential skill). It is about understanding the conventions and thought patterns of the people who construct the puzzles, who write clues designed to exploit double meanings and ambiguity, as well as cultural references keyed in to the experience of the perceived audience. Solving a good crossword is like looking somebody in the eye and saying “I see what you did there” with a wry smile. Who doesn’t enjoy that?
I have a few self-imposed conditions that make solving a puzzle especially satisfying. Making no errors is obviously ideal. I also enjoy when I can solve a puzzle while only building off answers I’ve filled in already, rather than having to jump around different corners. And of course, if I can solve it without referring to any outside resources I’m on cloud nine, but I still feel good if what resources I do draw upon are able to function without an internet connection. Peering over at my desktop globe to refresh my memory about the capital city of Malta just doesn’t feel that wrong.
(I have only limited experience with what are called “cryptic crosswords,” which are based on clues which are designed to be mind-bendingly… cryptic. My brain has not been trained on such things and I have not learned their secrets.)
What makes the puzzles in Will’s Best just the littlest bit harder is their age. Puzzles written only a few decades ago were written for a different audience than they are now, mainly an older one; clues from the 1990s or 2000s often have cultural references from the 40s or 50s. That’s not a huge issue for me, specifically, because I know all sorts of things about mid-century culture (and frankly more people should; educate yourselves on the treasures in the attic). The more important issue is divining the overall mindset of the crossword’s author, who wrote the puzzle in question with a set of expectations that can be hard to reconstruct from this remove.
But since I’ve reached this threshold, I’ve decided to invite you (the reader) along with me as I cross it. We’ll find out just how hard a three star puzzle from some time between 1993 and 2013 can be! I will fill in the answers one by one, noting my reasoning and relative level of certainty as I go. If I make an error, you’ll know it as soon as I realize it (if you haven’t realized it before). Without further ado, here is puzzle 261, constructed by one David Levinson Wilk.

(Apologies for the blurry edge on the scan.)
Beginning
A lot of these clues are presently opaque to me, so the first thing I have to do is find something I’m pretty sure I can do. 34 across, “When Nora leaves Torvald in ‘A Doll’s House,’” is probably ACT III, assuming that I’m correct in recalling that A Doll’s House has three acts. But in case I’m not, I look for evidence from some of the nearby down clues. 26 down, “A Mullah’s decree,” is probably FATWA. I’m more confident of this because 42 across, “Work unit,” is likely WATT. I’ll hold off on filling in 34 across until I’m more confident.
Glancing at 66 across, “Like Scorsese, but not Fellini,” I note that there are enough letters available to spell ITALIAN AMERICAN, and boldly decide this is likely the answer (Fellini was Italian, full stop). What a coup, getting one of these long ones right off the bat! And we can do it again with 67 across: “It begins ‘A well regulated Militia…” is obviously a description of the SECOND AMENDMENT of the U.S. Constitution.
Now we have a lot of help in filling in a slew of down clues on the bottom of the puzzle. 53 down, “‘I’m pointing at it,’” is likely THIS. 54 down, “Act feeblemindedly,” is likely DOTE. Glancing at 53 across, “Elicitors of little dances, briefly,” I see that the answer is TDS, that is touchdowns (briefly). 55 down, “Disconnected, in music” looks like “STAC,” which would be short for staccato, and I think it probably is because 62 across, “August comment,” begins with HO- and is highly likely to continue with T.
63 down, “Inits. in 70’s-80’s rock,” is clearly ELO (Electric Light Orchestra, for the youth). 64 down, “A leg that gets whistled at,” has got to be GAM, leaning into some very old-timey slang for shapely limbs. That E and that G are enough to persuade me that that 62 is most probably “HOT ENOUGH FOR YOU,” which would mean that the answer to 65 down, “Net holder,” is RIM (makes good sense). 57 down, “A large moth,” now looks very much like LUNA. 49 down, “Message on a dirty car,” is probably WASH ME. 51 down, “Tons,” is looking a lot like A LOAD. But now, alas, I am feeling a little stumped by the rest of the clues in this area. It may be time to jump around again.

Progressing
40 across reads “Musicians whom orchestras tune up to,” and the answer is clearly OBOISTS. 29 down, “Ski-___,” is all the more likely to be DOO (you see this answer fairly often in crosswords, and it’s usually clued by Ski- rather than Scooby for some reason). 32 down, “Coup follower” is most likely DETAT. 30 across, “Loses,” almost certainly ends with S, because the person and tense of a verb or the number of a noun (that is, whether it is singular or plural) is always significant in a crossword clue, but I can’t figure out the rest of it; neither am I sure which abbreviated S word can satisfy 33 down, “Ways: Abbr.” I usually don’t fill in letters unless I’ve got an entire answer (it looks so lonely, dangling out there), but sometimes having a letter I’m sure of can help me think, so I’ll just put that S there for now. But I think we must be jumping again, and we may be jumping for a while.
9 down, “Madrid maze-runner,” suggests RATA (Spanish for rat, because Madrid is in Spain, you see). 12 down is “John,” and with three letters I am fairly certain the answer must be LOO (crossword creators love their Britishisms and potty humor). 13 down reads “Last one _____…” and suggests to me the answer IS AN, which I am going to go out on a limb and endorse as the probable answer. 8 down is “Uintah and Ouray Reservation inhabitant,” and I’m not familiar with those particular reservations, but there aren’t that many groups of indigenous people with only three letters and UTE is one of them, and crossword creators do love UTE… we’ll keep that in our back pocket though.
1 down is “Member of the Allies in W.W. II: Abbr.” and with four letters I can’t believe I didn’t put USSR the instant I saw that. 19 across, “Full house sign,” is probably SRO (standing room only); crossword people love abbreviations like that. A quick glance at my bookshelf confirms that 5 down, “Aeschylus trilogy,” has got to be the ORESTEIA. This drops an I right where it would need to go if the answer to 34 across were indeed ACT III, and at this point I’m prepared to ink it in.
I took another look at that troublesome lower right corner. 59 across is “67-across citers: Abbr.)” and that sounds like the NRA to me; 59 down is “Inits. on many A.T.M.’s” and given that we know the second letter is Y, and that this puzzle first appeared in the New York Times, NYCE seems as good as anything else (I don’t know what the last two letters stand for, though). That means 60 down, “Sheepskin leather,” is ROAN, and 61 down, “Volunteer babysitter, maybe,” is AUNT. I kind of forgot that U could come after vowels sometimes…

Continuing
I took a little break, and I’ll probably take a few more before we’re done. You can’t always get these all at once! Sometimes you need fresh eyes. I can’t say why else it didn’t occur to me sooner that the answer to 25 down, “Reply to ‘the phone’s for you,’” had to be WHO IS IT. That makes it clear what 30 across has to be: SHEDS. No more dangling S!
A good long look at 36 down, “Osteoarthritis treatment,” led to the sudden realization that the answer was IBUPROFEN. That gave me enough letters in 48 across, “Some tracks,” to recognize the answer was assuredly PAWPRINTS. 44 down, “It might be filled with ink,” is probably SAC on that basis. 45 across, “Beat in November, perhaps,” looks to be UNSEAT (having defeated the incumbent in an election). That makes 41 down, “Public,” certainly ON RECORD. Thus we know that 52 across, “Sticking Point?” is CARET; that question mark is a crossworder’s standard signal that a bit of wordplay is happening (a ^, or caret, marks the point in which you stick something that is missing from the text, you see). Finally, it also shows that 58 across, “Alternative to Rep. or Dem.,” is SOC, short for “socialist.”
Examining the intersecting clues of 31 down, “‘The Other Side of Oz’ autobiographer,” 33 down, “Ways, Abbr.,” and 37 across, “Follow,” I conclude that the answers must be EBSEN, SYSTS, and OBEY, respectively. My French is a little rusty (I don’t have very much) so I didn’t immediately pick up on 35 across, “Man wearing une couronne,” but with two out of three letters revealed it’s got to be ROI (couronne is crown, you see).

Sleeping On It
Sometimes a puzzle can be a multi-day project, and that’s OK! Sometimes it takes you more than a decade to get halfway through a book! Time is an illusion!
Appropriately, the first clue I solved this morning was 38 across, “It’s often hit at night.” THE SACK, you see. 39 down, “Silent lawman?” is of course another bit of wordplay; the answer is KOP, after the Keystone Kops, popular characters in comedy films from the silent era. 43 across is “Daughter of Hyperion,” and I did not remember this character’s name at the start, but the letters I have revealed thus far strongly suggest that the answer is EOS, a name I know from Greek mythology.
The other thing that is good about a good night’s sleep is you can realize when you’ve made a bone-headed error. 13 down is clearly wrong; I mangled the phrase, which should read “Last one IN IS…” I’m still not sure what the answers that cross that column are, but I’m glad I found that mistake now. Scribble scribble…
24 across, “One going back and forth to work,” is a SAW. I know this because the last letter of 10 down, “Ices, maybe” is almost certainly an S, even if I haven’t figured out the other letters yet.
Speaking of errors, a shadow has been growing across my mind. A consultation with my dictionary confirms that the WATT is the SI unit of power, not work, and this is almost certainly significant. This throws the answer to 26 down, FATWA, into doubt, even as 34 and 38 across seem to have confirmed the A and T. In addition, 27 down, “Fall shade,” seems like it ought to be OCHRE, except that WATT puts an A where an R should be. What a mess, right where we began! I’ll scratch out the ATT, but leave the W of FATWA for now. I’ll go ahead and add in OCHRE too. In fact, FATWA is looking even stronger now, because that O strikes me with the answer to 26 across, “Replacement raiser:” FOSTER DAD.
28 down, “Composition of some Nerves?” looks now like it must be STEEL. 22 across, “Look ____!” is probably either AT HIM or AT HER, but either way it makes it seem very likely that 22 down, “Start of an Ella Fitzgerald standard,” is A TISKET. This would make our mysterious “work unit” of 42 across WREK, which I guess I’ll just have to accept for right now. Meanwhile, I’m troubled by 46 across, “It’s on the Rhone delta,” because the first four of five letters are evidently AELE, and I do not know what to make of this.
50 across, “Kind of cart,” now seems like it must be TEA. I’ve been thinking for a long time now that 56 across, “Wing,” must be ELL, although the sense that would make this obvious escapes me. However, if they are both right, it suggests a sensible answer for 47 down, “Like guests at home:” SEEN IN. I’m going for it; this would also make 46 across AELES, and I guess I’m just making my peace with that.
Son of a gun. OCHRE isn’t always spelled like that. Apparently it’s OCHER here in the U.S. of A. That makes the work unit WEEK and the site on the Rhone delta ARLES, a place I have heard of. I’m much happier with that, even if I do prefer the international spelling of the color in question.
I’m glad I haven’t committed to either AT HIM or AT HER for 22 across, because I am increasingly doubtful about that H; the letters I have for 6 down, “Legendary 49ers receiver,” makes it phonetically problematic, and I know very little about football. We’ll come back to that later.

Polishing Off
After dinner, a cocktail, and taking in a baseball game, it’s time to start getting bold and try to finish off this top quarter, and thence the puzzle. 21 across, “Old map abbr.,” looks like SSR to me (for Soviet Socialist Republic, something you don’t see on contemporary maps). 14 down, “Boarding places: Abbr” most likely ends in S, reinforcing the point. Lots of abbreviations in this one, huh? It’s tricky because you can’t always be sure how exactly something will be abbreviated. I’ll go ahead and add UTE to 8 down now. Worst case scenario, I have to scratch it out.
There’s another clue, 23 down, that reads “Old map abbr.,” and with the letters I’ve got I’m going to say that it’s UAR (United Arab Republic). That clarifies 22 across considerably; it’s AT YOU, no H required. From out of the depths of my mental list of famous people, a name comes to me for 6 down: JERRY RICE. Putting that J down makes it clear to me that the answer to 1 across, “Writing that lacks objectivity,” is some kind of JOURNALISM, but I can’t quite figure what kind yet. It’s not YELLOW, there’s not enough letters for that. But I’ll fill in the letters I’ve got, because this is a game of inches now.
With the letters I now have for 7 down, “Charles of CBS News,” I think I’m prepared to say the answer is OSGOOD. I don’t specifically remember a Charles Osgood from CBS news, but it is a surname that exists and would fit, and I am beginning to believe that the second word of 16 across, “Purveyors of spicy cuisine,” is RESTAURANTS. The only problem with that is it would invalidate LOO for 12 down, but I think I’m onto a better replacement. You see, 1 down is also wrong, though I haven’t quite figured out the correct answer yet; 17 across, “‘Hurry, you’ll be late,’” is BETTER GET MOVING, which confirms my dawning realizations that 15 down, “Religious title: Abbr.,” is MSGR (for Monsignor) and 14 down, “Boarding places: Abbr.” is STNS (for stations). It’s all coming together now: 11 down, “Bakery output,” is AROMAS, and 10 down, “Ices, maybe,” is NUMBS. This also fills in 20 across, “Patriot, e.g.: Abbr.,” which has been extremely opaque to me this whole time, but ABM are the initials of anti-ballistic missile, which a Patriot certainly is. And the true answer to 12 down is not LOO, but LAV (it’s still potty humor and Britishisms).
As I said, 1 down was wrong, and scratching out that U gives me the clarity to see that 1 across is GONZO JOURNALISM. 4 down is “Proactiv target, informally,” and it took me this long to remember what Proactiv is for, but the answer is ZIT. With that I, it seems more than likely that 16 across is THAI RESTAURANT. 1 down now looks like it’s got to be a four letter abbreviation for Great Britain, but with GTB_, is the fourth letter R, or N? It’s a tough one.
I’ve been thinking for a long time that the answer to 2 down, “Expressed surprise,” most likely ends in D (being a past-tense verb and all). Now I have to conclude that the answer is OHED, as in “said ‘oh.’” Not a great word, but we accept the reality of what is written. 3 down, “R.F.K. Stadium team, briefly,” has got to be NATS. At this late stage I will allow myself a quick search for verification; and yes, the Washington Nationals did play at R.F.K. Stadium from 2005 to 2007. I guess they’re going to tear it down soon, bummer. Incidentally, this gives us a fairly narrow span of time in which this puzzle could have been constructed, which is a fascinating little detail for somebody like me.
And now it comes down to one square. 18 across is “Tpks.,” and if I’m right about 1 down then the answer is most likely either RDS or NDS. I was about to write a whole thing about how frustrating it is to come up against something so maddeningly vague, and then it hit me: “Tpks.” is probably an abbreviation for turnpikes, which means that the answer is RDS (or roads). So 1 down is GTBR, after all.

Hell Yeah
I looked up the answer in the back of the book, and if you ignore a few unsightly pen scratches I’ve got it 100% correct. Three stars, nothing!
Granted, it’s not the cleanest triumph in my crossword career, but I feel really good about this one. I was worried that, in my hubris of tackling a puzzle in front of an invited audience, I might not be able to solve it completely, and I’d have to hang my head in shame. But this turned out to be just as fun as I hoped.
I have no idea whether following along as I reason my way through crossword clues is actually good reading, but my hope is that anybody who is curious about this pastime but doesn’t quite know how to go about solving one will take heart and inspiration from my example. There are lots of ways to tackle an open-ended puzzle like this, and I’m sure some of you would have figured out a few of these clues way before I did. The satisfaction, however, lies in making your own way, putting the pieces together until everything fits nicely. Then you can go on Wikipedia and learn about the connection of people like Buddy Ebsen to The Wizard of Oz (the poor guy was allergic to the Tin Man makeup and the role had to be recast).
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