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]
Surviving Sudoku. Matt Gaffney, a crossword puzzle designer, examines the crossword community's ambivalent relationship with the phenomenally successful number puzzle. Meanwhile, it's high time to resurrect Done in Pen: The Poems of New York Times Puzzle Editor Will Shortz.
The 2003 American Crossword Puzzle Tournament is coming March 14-16. You can either participate in person by going to Stamford, Connecticut for the weekend, or play at home on your own time. If you're a confirmed or aspiring cruciverbalist, you should check this out -- the puzzles are great and the competition is light-hearted. (Will Shortz (right), director of the tournament and editor of the New York Times crossword puzzle, was recently interviewed on 60 Minutes.)