Film Wordplay (Patrick Creadon, 2006)
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The film has discussions with a number of celebrities about their interest, skill, and habit of doing crosswords. President Bill Clinton, television humorist Jon Stewart, master documentary filmmaker Ken Burns, baseball player Mike Mussina, retired Senator and presidential candidate Bob Dole, and singers Indigo Girls all appear in interesting discussions several times in the film.
One particularly interesting story that both Bob Dole and Bill Clinton told was the Times puzzle, on the eve of the 1996 presidential election which pitted them against each other. That puzzle included a 2-word horizontal solution to something like "tomorrow's headline" - and the puzzle worked with phrases like either "BOBDOLEWINS" or "CLINTONWINS" - with all intersecting vertical words having solutions with corresponding letters from either choice! (I found a site where you can read more about this and which allows you to do the puzzle after installing some software.)
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I have never been good at crosswords, though I think I am reasonably literate and at problem solving. Visiting online crosswords at USA Today (which gives immediate feedback when an incorrect letter is typed) and thinks.com tonight after the film confirmed my poor skills. I also found an amateurish crossword maker.
The film was well made and fun to watch. In addition to reading about the film on imdb, one can also visit the official film website.
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