What’s the hardest word to solve in Hangman?
If you guessed some freak of linguistics like “onomatopoeia,†“dybbuk,†or “benzodiazepine,†you’re barking up entirely the wrong arboriform growth.
Take it from Jon McLoone, director of business development for Wolfram Research, the company behind popular mathematical modeling tool Mathematica. McLoone was inspired to investigate the English language’s hardest-to-guess word after his six-year-old daughter asked him how she could beat her Hangman computer game.
To find out, McLoone wrote a program that would play Hangman with all 90,000 words in the dictionary, attempting to guess each one in a semi-random way similar to a method a good human player might use. In total, he simulated some 15 million Hangman games, tying up several office PCs for a weekend in the process.
“Difficult,†for example, isn’t very difficult to guess at all, taking on average 3.3 wrong guesses per game — not even close to losing. Contrary to his expectations, McLoone found that shorter 
words were harder to guess than longer words, and the fewer pieces you use in your Hangman drawing, the truer that gets.
And the hardest of all? “Jazz,†which topped the rankings in all the variations of the basic game he tried.
McLoone also lists the top 25 hardest Hangman words, according to his program. Words with double Zs or Fs, like “buzzer†or “faff†rank high, but he suggests players pick longer words to fool their opponents.
“You can’t beat “powwowing,†“bowwowing,†and “huzzahing†for entertainment,†he suggests..