If you haven't seen the movie Wordplay, do yourself a favor and watch it. Will Shortz is a central figure in it and seems like a true word hacker.
Also a shameless plug, I run a crossword puzzle database that maps the relationships between answers and clues (I wanted to see what clues pointed to what answers and vice versa). It may be of interest here:
Second the Wordplay recommendation. I believe that's where he stated that his favorite crossword clue ever was "It might turn into a different story" for the word SPIRALSTAIRCASE.
BEQ, an NYT crossword constructor, did a Reddit IAMA the other day. He mentioned a favorite clue and solution being {Take cash but not credit} for GHOSTWRITE. I'm always the most satisfied whenever I successfully fill in a solution for clues like these.
That's covered a bit in the Wordplay movie, they had both Clinton and Dole comment about it (both saying they knew they won because it said so in the NYT crossword).
One thing I found fascinating was the difference between US and UK crosswords, which I'd always assumed would be pretty similar:
"Crosswords in England are completely different from ours ... their crossword clues started including anagrams, homophones, hidden words and other wordplay ... cryptics here have never achieved widespread popularity."
If you're interested, a clue in a cryptic crossword in the UK must give you the answer two different ways, one of the ways is a synonym/description, and no word may belong to both of the ways. Sometimes a setter will not meet these criteria, so they append a question mark to the clue to mark it as not quite proper.
For example, "reprimand son for being so unfeeling" is scold -- a synonym of reprimand, and then s for son and cold for unfeeling.
I enjoy doing the cryptic crossword in our local paper. Unfortunately, the ones in national papers are too hard for me. Often the trick is knowing something like that a sailor used to be called a "tar".
They are a lot of fun though; I prefer them to general knowledge since all you need to answer them is time, lateral thinking and a good vocabulary. They are also a great illustration of the workings of the subconscious -- coming back to a puzzle after a short time usually yields some answers instantly.
The most popular crosswords in the UK are the same type as those in the US. But some newspapers have an additional 'cryptic' crossword. (I don't know more than a couple of people who actually do the cryptic crosswords, but I guess they must have some sort of following.)
But the people who do the Times cryptic everyday during their commute know they're in a different class... (e.g.: http://times-xwd-times.livejournal.com/731666.html ). I certainly can't make much of a dent in a cryptic crossword, though the 'concise' ones are sometimes doable.
That actually surprised me, in reverse (I always assumed the NY Times Crossword, at least the 'really hard' Saturday one, was a cryptic crossword). Personally, cryptics are the only ones I really do anymore - I go through phases where they're the only thing to put me to sleep at night, which I assume is something to do with the way they focus the mind.
GAMES magazine usually has a few cryptic crosswords per issue, so if you want to give it a try pick up an issue. I'm sure they've also got collections out there... or you could probably look for used issues to play with. I know all of my old issues had unsolved cryptics.
What interests me most about Will Shortz is the insight his his life and his spots on NPR have given me onto the natural human love of puzzles.
Although I personally do not get much of a kick from solving puzzles for their own sake, I definitely want to understand those who do. Seeing mathematician John H Conway give a lecture was also interesting because he was deriving immense pleasure from something while up on the stage -- and my best guess as to the nature of that something is puzzle-solving. Until that lecture, it had not occurred to me that puzzle-solving could be such an immense source of pleasure.
Nitpick: BEQ, the guy who did that AMA, is a crossword puzzle constructor who has had some puzzles published in the NYT. Will Shortz is the NYT crossword editor.
Seven people basically check each puzzle by hand, and yet it still isn't 100% foolproof? That seems hard to believe for the level of skill all these people have minus the freelancer.
Will knows when to be a pedant, and when it's necessary not to be a pedant in order to communicate more effectively. Some people don't know when not to be a pedant - I tend to be one of them - and it's interesting to see Will transcend that.
No, we call them crosswords. ("Cryptic crosswords" when it's necessary to distinguish them from the sort that's dominant in the US, and yes, that can be abbreviated to "cryptics", but that wouldn't be the norm.)
I'm guessing that the complaint was actually about "England" versus, say, "the United Kingdom".
I made up a word game in high school that became popular with my friends - tell me what you think. Basically, you solve for one word. The clues are words that have at least one letter from the word, in order, that have something to do with the word.
Interesting game. I admit, I wouldn't have gotten it without help from the internet, which I suppose is against the rules. But I know no latin, so it was my only hope. The answer is ursine, which I've attempted to bury somewhat in my response so that it doesn't pop out so obviously to those who read this later and want to solve the clues for themselves.
Here's a stab at one that's so vague that there's probably a better answer hidden in there than the intended "right" one:
Team up with someone who wants to make it an app, then!
It's natural for a touch interface: each word made up of scrabble-like tiles with a letter on each, tap the letter(s) from each word that spell out the answer and submit for a score. Or, if you wanted to get crazy, you could play heads-up, but you'd need a whole lot of clues/answers lined up if you wanted to go that route (so if you wanted to go really crazy, string together some databases and programs to auto-generate each puzzle).
Ah, I was bitten by not being a native-speaker. I've interpreted "hibernate" as the same thing my laptop does, when it hibernates. And cats do that all the time, right? ;-)
Also a shameless plug, I run a crossword puzzle database that maps the relationships between answers and clues (I wanted to see what clues pointed to what answers and vice versa). It may be of interest here:
http://crosswordtracker.com/