Some heads-ups about grids in the wild: On Tuesday, the New York Times crossword is a #rosswordpuzzle. I hope you enjoy it! And this past week, I co-authored puzzles with both Nina Sloan and Jessie. Give them a solve!
Also, last call for the Boswords Spring Themeless League, which kicks off tomorrow night. Parker and I are going to do our Monday Cursewords stream directly thereafter, right around 10pm eastern. We hope to see you there! Presumably to do some mass commiserating in the chat…
I started working on today’s puzzle after watching “Framing Britney Spears,” a NYT documentary about her court-sanctioned conservatorship. As a child of the 90’s, it’s … a lot to take in. I recommend it. Thoughts and spoilers for “Repeat Offender (Free Britney!)” after the jump!

One OOP … *two* OOPs?!
It sort of surprised me that OOPS I DID IT AGAIN (15) hadn’t even been used as a double-hidden-word revealer in the mainstream, but the truth is there just aren’t that many OOP … OOP answers out there, and the whole puzzle kind of hinged on finding POOPER SCOOPER, which fails the standard breakfast test. But this is the *internet*, so anything goes. Oops!
I would have preferred to find all 2x OOPs that *didn’t* have an S after the OOP (as in SHOOP SHOOP SONG), but again, limited options. So here we are, humming Cher together. If you wanna know, if he loves you so…
And it just worked out that the letters across the theme answers were conducive to a lower word count grid (74), which allowed for a PILE-UP of fun (or at least fun to clue) longish down fill: METERMAID, ED SHEERAN, DIPLOMAT, AP BIOLOGY, STAR PUPIL, ROUGH IDEA.
Happy solving, friends!
-Ross
It seemed odd to me that you would used the etymology from the latin to clue a Russian despot and then spell the word in what I consider the crossword friendly but for me less preferred spelling of czar/tsar.
Two of my most favoritest things to talk about: “duping” answers and cruciverbia’s strongly-held TSAR/CZAR opinions!
That clue definitely wouldn’t fly in mainstream xwords, but I’m on-record as pro “disrupting” conventions around duplicating puzzle words. In this case, it struck me that a lot of people probably haven’t considered the etymological relationship between the words, and so more interesting that another “Bygone autocrat” offering.
We also have the German “Kaiser” from Caesar, which you don’t see too often in crosswords. The link between those two words seems really obvious. Well, to a retired German teacher, anyway.
Yeah, Kathy, this very well could be another example of Ross thinking “whoa! I bet nobody realizes that!” … when it’s just Ross.
what fun themers! the breakfast test stifles true brilliance….
I think Ruby wrote #24 as a reminder for me 🐱🐱
When you’re right, you’re right <3