Stephen Sondheim's crossword puzzles for "New York Magazine." Incredibly rare.
posted by grumblebee on Oct 29, 2009 - 35 comments

EclipseCrossword is a powerful windows tool for automatically creating crossword puzzles. You can create multiple puzzles from the same word list; print the puzzles in assorted formats; or export interactive puzzles for web pages. [more inside]
posted by Mitheral on Dec 8, 2008 - 9 comments

XWord Info soberly describes itself as containing "data about NYT puzzles dating back to November, 1993, covering the entire time that Will Shortz has been Puzzle Editor," understating the cornucopia of geeky goodness within. See any crossword over that time. Look up every appearance of a word with every clue ever used for it. See the most frequently used 500 words, and the most popular by length. [more inside]
posted by Zed_Lopez on Dec 7, 2008 - 42 comments

NYTimes Crossword Drawings. Emily Jo Cureton creates an illustration for every Times crossword, using a handful of clues to create odd little scenes. [via]
posted by mediareport on May 6, 2008 - 24 comments

The Ephemera Society was glancingly mentioned prior, but deserves a better mention. It includes:
—An exhibit, an article, and links to Michael Ragsdale's 9/11 ephemera.
—A history of Coca-cola print ephemera.
—An article by Will Shortz on the ephemeral history of the crossword.
—Articles from the Louisiana Library Association's journal issue on ephemera, including Principles for Organizing an Ephemera Collection and an Overview of Political Ephemera.
posted by klangklangston on Jan 5, 2008 - 11 comments

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]
posted by painquale on Jan 22, 2007 - 26 comments

Tyler Hinman: Legend, Zoalesquianist, Champion. The American Crossword Puzzle Tournament has a new kid in the grid.
posted by DeepFriedTwinkies on Mar 14, 2005 - 4 comments

A New York Times crossword puzzle printed on November 5, 1996, election day, was designed to predict the winner of the election, no matter who won. That takes some skill to design.
posted by BradNelson on Dec 16, 2004 - 20 comments