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A New Frontier in Artificial Intelligence

Will computers be able to solve cryptic crosswords?

Joshua Kosman and Henri Picciotto

March 14, 2013

Do you have an interest in cryptic crosswords and a facility with the more intricate realms of computerized artificial intelligence? If so, there’s a project out there with your name on it.

One of the more fascinating recent developments in the word of cruciverbalism has been the birth of Dr. Fill, the wittily named—and frighteningly proficient—crossword-solving program developed by puzzle constructor and software engineer Matt Ginsberg. Operating on brute speed to compensate for his lack of common sense, Dr. Fill has penetrated the lower ranks of good solvers. He (it’s hard to avoid following Ginsberg’s example by personifying the good doctor) is not yet in the upper echelons of solvers yet—but don’t look back, because he’s gaining on us.

Dr. Fill made his debut a year ago at the American Crossword Puzzle Tournament in Brooklyn, solving the puzzles alongside a field of nearly 600 contestants and finishing in 141st place. Last weekend he returned, and improved his standing to ninety-second. (In the human division, meanwhile, solving wizard Dan Feyer sailed to a fourth consecutive victory.)

Ginsberg regaled the assembled contestants with a fine and highly educational presentation about just how Dr. Fill operates. He doesn’t try to find a short path to the smartest solution; rather, he makes lots of not-too-stupid guesses and then uses his processing power to sort through the possibilities and find the ones that cross each other.

But there’s one thing Dr. Fill doesn’t know, and isn’t about to learn—namely, how to solve cryptic crosswords. And the reason is simple: Ginsberg isn’t interested enough to teach him. Much of his development time is spent training Dr. Fill to recognize things like puns, rebuses, added-letter themes and other tricks that are common in standard crosswords.

Dr. Fill could easily be trained to spot comparable principles in the world of cryptics. All he needs now is a trainer—and Ginsberg told the Brooklyn crowd that he’d be happy to let someone else take a crack at it. Unlike Watson, the computerized Jeopardy! champion developed by IBM, Dr. Fill isn’t a commercial undertaking (although some of the databases he relies on are proprietary). So all he’s waiting for is a software and cryptics guru willing to show him the ropes.

Do you have the interest and expertise to adapt Dr. Fill to the world of cryptic crosswords? Please weigh in here, along with any quibbles, questions, kudos or complaints about the current puzzle or any previous puzzle. To comment (and see other readers’ comments), please click on this post’s title and scroll to the bottom of the resulting screen.

And here are three links: • The current puzzle • Our puzzle-solving guidelines • A Nation puzzle–solver’s blog where you can ask for and offer hints, and where every one of our clues is explained in detail.

Joshua Kosman and Henri PicciottoJoshua Kosman and Henri Picciotto are The Nation’s puzzlers. To read more about Kosman, click here. To read more about Picciotto, click here. Kosman and Picciotto explain what they’re up to in “Solving The Nation’s Cryptic Crosswords” (also available as a PDF). Check out The Nation’s Current Issue page each week for the latest puzzle.


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