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Mathematician Jon McLoone calculated the most difficult word to guess in the game of Hangman. It's "jazz". Here's how he arrived at that result:

Jon McLoone built a computer game -- with a series of algorithms -- to figure out that exact question. It rests on a key assumption: the guesser will pick common letters (e.g. vowels) measurably and proportionally more often than exceptionally rare ones (Q, X, Z, J). McLoone then simulated fifty Hangman runs for every single word in the dictionary. That's 90,000 words, totaling nearly 5 million games on Hangman.

Some words were easily guessed, typically requiring fewer than five incorrect letters offered. For example, the word "difficult" proved easy -- in its 50 trials, the simulator guessed, on average, only 3.3 incorrect letters. Allowing for eight incorrect ones before our stick figure meets an untimely death, the word "difficult" only caused one stick-death. Allowing for ten? Mr. Stick had a 100% survival rate.

Having gathered all this data on 90,000 words, McLoone selected the 1,000 most promising, and then ran the game 3,000 times using just those thousand. All said and done, McLoone "played" nearly 8 million games of Hangman in order to determine that the hardest Hangman word to guess -- regardless of whether the guesser has 8, 9, 10, or even up to 13 guesses, is "jazz."

Link via reddit | Photo by Flickr user quinn.anya used under Creative Commons license

Simulating a more 'human like' guessing can be done that way, but that's not really modeling an AI to think, and thus guess, like a human. The actual human thought process (speaking in terms of information, even leabing out the biological 'mechanics' of it) is WAAAAAAY more complicated than anything we've been able to do in the field of AI thus far. (And the AI subsection of Computer Science is a particular strong suit of mine).
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syzygy actually isn't that hard - usually people guess vowels first and when they are forced to guess Y, it's a giveaway for anyone familiar with the word
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