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Across and Down, Wordplay's a Winner

05/04/2006 09:20 am ET | Updated May 25, 2011

As usual, Jon Stewart said it best. "I'll do a USA Today crossword if I'm in a hotel, but I don't feel good about myself afterwards." He grimaced when he said it, making us know that he didn't just not feel good, he actually felt kind of unclean. "Bring it on, Shortz!"

The Shortz he's referring to is Will Shortz, The New York Times crossword puzzle editor and NPR Puzzlemaster who is the subject of Patrick Creadon's magical new documentary

Wordplay follows Shortz as he hosts the 28th annual American Crossword Puzzle Tournament, in Stamford, CT. He founded this competition, which now attracts more than 500 solvers each year. At the ACPT, Shortz is the king, but he's also a mensch, visibly enjoying the event and the cast of characters that shows up year after year.

The film trails several elite puzzlers as they prepare for the tournament. I wouldn't call them freaks, but they do seem to be wired in a different way. They start at the upper left hand corner and steadily work their way down to the lower right. They don't use any of my cheating tactics, like making up words to fill in the boxes, or inserting a "gender-neutral" letter. They finish the Sunday puzzle in about 10 minutes, and that's without the Internet, a thesaurus or a frantic phone call to a museum curator. Former ACPT champion and professional crossword constructor Trip Payne discusses moving to Southern Florida to escape New York's puzzle community. "The first time I saw the sign for the Intercoastal, I noticed that it was an anagram for 'altercations,'" he says. Indeed.

Shortz doesn't actually create the crosswords. He edits them and writes most of the clues for the 365 puzzles the Times prints each year, purchased from more than 100 puzzle constructors. One of the more prominent puzzle constructors, Merl Reagle, mentions that the Times uses the "Sunday breakfast test" to decide whether or not a word is acceptable - the idea being that people are doing this puzzle over their Sunday breakfast. Given the "scumbag" kerfuffle of last month, perhaps the rule has since been revoked.

Daniel Okrent's not going to tell. He's too busy doing the puzzle. The New York Times' first Public Editor shows the notebook he's kept for years. It's filled with columns of dates followed by the number of minutes and seconds it took him to solve the puzzle that day.

Bill Clinton notes that he became an avid puzzler while in the White House, and says that now "half the time I do these things just to see what people are thinking about." Which is a point both Shortz and Okrent make emphatically - the puzzle needs to be a reflection of the times, and of The New York Times and of what's going on in the world.

There's much more to say about Wordplay, but I don't want to ruin it for anyone. If I were in charge, I'd give it the Best Documentary Oscar next year. And with these guys on the distribution team, I'm sure the film's being positioned to do just that, at the very least.

Tomorrow morning, I'm going to try the New York Times crossword puzzle again. It's something I haven't done in a while, and "Wordplay" really made me miss it. Bring it on, Shortz!