[Henry] Hook has come to be known as the Marquis de Sade of the puzzle world: a brilliant and oddly beloved misanthrope, administering exquisite torture through dozens of puzzle books and syndicated crosswords.
Derek Crozier was an idiosyncratic crossword setter who, under the pseudonym Crosaire, ran the Irish Times cryptic crossword singlehandedly for almost 70 years. He died in April 2010 at the age of 92, having compiled over 14000 daily crosswords. The last puzzle completed before his death, number 14605, runs in today's Irish Times. [more inside]
Stephen Sondheim's crossword puzzles for "New York Magazine." Incredibly rare.
Since Wordplay has come out, crossword puzzles have been on the rise. If you want to join in on the fun, read this primer by Will Shortz to get started, then download Across Lite, head to Cruciverb, and do free puzzles in the right-hand sidebar. Will Johnston's page contains a huge repository of Across Lite puzzles. If you get stuck, can't figure out why an entry is correct, or just want to chat about a grid's brilliant construction, try reading the crossword blogs. The best two are Diary of a Crossword Fiend and Rex Parker Does the New York Times Crossword Puzzle. (Caution! Spoilers abound!) And, if you want to try your hand at constructing some crosswords of your own (submission guidelines for various papers here), Crossword Compiler is an outstanding piece of software. [Via this AskMetafilter question]