You may have seen that story about "jazz" being the hardest Hangman word. Personally, I always figure that such a short word is hardly fair, but I'm not that good at Hangman. The inside story of how they figured out the hardest words is kind of interesting -- it involves a guy writing a Mathematica Demonstration to play Hangman and his daughter getting annoyed at never being able to beat the computer and its dictionary.
(via Chad Orzel)