tl;dr

I can stop doing cryptic crosswords any time I want to. I just don’t happen to want to right now.

In Fall 2009, my wife finally succeeded in her long attempts to get me to start doing crosswords. As a child, I once filled out a newspaper crossword that advertised a $100 prize and sent it in, confident in my newfound wealth. I was bitterly disappointed when the next week’s paper came out with no mention of the crossword having been solved, and indeed no money arrived. I decided that crossword authors were capricious and gave up on the genre.

My wife’s help was really important. I learned about “crossword words;” she would look at a clue and give me a word that I’d never heard. I would blink and ask her what it meant, and she’d just say “I don’t know; it’s a crossword word.” I learned that any clue in four letters that references a dog in a movie is about 85% likely to be Asta (from the Thin Man movies); 10% likely to be Toto (I don’t think we’re in Kansas anymore), and 5% something else, and if you have only one crosser in the third letter you just can’t fill it in until you get one more crosser, though you can guess at Asta and see if it helps you with any of the crossers. I learned, also, that you are expected to have an encyclopedic knowledge of Broadway, the silver screen, and popular music; including the winner, runner-up, and second runner-up for every award ever given in any entertainment venue. Blah. I know next to nothing about popular entertainment culture.

After we had finished one book full of NYT dailies, I griped to a co-worker (Thanks, Andy!) about all the required esoterica, and he introduced me to the cryptic crossword, in which each clue is a word puzzle. He told me to get a book that had an introduction to how the word puzzles worked.

By sheer luck, I happened on what I believe is the absolute best book to start with: Fraser Simpson’s 102 Cryptic Crosswords. Fraser Simpson, a Canadian math teacher, is one of the most stringent practitioners of a strict rule for making each word puzzle fair. He gave this newcomer to cryptics the ability to trust that the clues would make sense, so that I didn’t throw it down in disgust.

I heartily recommend Simpson’s work for getting started. After his “102” (all of which he constructed), I would suggest 101 Cryptic Crosswords: From the New Yorker which he edited. The style isn’t quite as consistent, since he’s the editor, not the sole constructor. Getting used to the different styles is an excellent way to launching into more cryptic crosswords.

From there, there are really two ways to go. There are two basic schools of thought in cryptics. One tries to stick fairly strictly to the rules of fairness set out by “Ximenes” (Derrick Somerset Macnutt), and the other is rather looser. In the stricter school, if the solver has to understand that you are using a word with an invented meaning or as a pun, the constructor (or “setter”) is expected to tell the solver (normally with a question mark). In the looser school, you are just expected to figure out that (for example) a “flower” might be a river (because it flows) or a “banker” might be a river (because it, um, has banks), so that “italian banker” would “obviously” clue “po”. In practice, there are perhaps a few hundred or few thousand of these odd constructions that solvers just memorize, as an esoteric jargon. In my opinion, this detracts from the beauty of the puzzles while making them less accessible, and is a concession to setters who have trouble coming up with better clues.

If this has piqued your interest, I strongly recommend the two Fraser Simpson collections, and then after that, there are several possibilities: