The hardest hangman words, and the maths behind them

What is the hardest hangman word?

Jazz. The answer comes from a piece of work that is still the most thorough anybody has done on the question: in August 2010 Jon McLoone took the 90,000-word dictionary built into Mathematica, wrote a guesser that picks letters by frequency, and simulated 50 games for every single word, then another 3,000 games each on the top thousand. His conclusion was blunt: jazz wins most for all game sizes.

It is worth being precise about what wins means there. The study measured how often the word beat a competent guesser, not how unusual it looks. Jazz is four letters long, three of which are J and Z, the two letters a sensible guesser reaches for last. Guess the vowels and you get one A. Guess the common consonants and you get nothing at all. By the time anybody thinks about J, the drawing is finished.

Why is jazz the hardest word in hangman?

Because it fails the guesser on all four counts at once, which almost no word manages. It has three distinct letters in four positions, so there are only three chances to be right. It has one vowel. It carries two rare letters. And the double Z means solving half of it solves nothing, because the remaining blank is the same letter you already have.

Compare it to the words people reach for instead. Here are ten of the hardest hangman words with the numbers that decide them, and the pattern is the same every time: the distinct-letter count is low, the vowel count is one or zero, and the rare-letter column is not empty:

Rhythm and syzygy are the extreme cases: neither contains a single A, E, I, O or U. A guesser who opens with the five vowels, which is what almost everybody does, has spent five guesses and learned nothing. Queue is the joke of the group, because four of its five letters are vowels and it still wins, since three of them are the same letter.

Why are short words harder in hangman?

This is the counterintuitive result, and McLoone found it too: the top of his difficulty ranking is dominated by three, four and five letter words. The reason is that a hangman board leaks information. Every letter you fill in tells the guesser about the letters you have not filled in, and a long word simply has more of them to leak.

Write a fifteen-letter word and the guesser's first five ordinary guesses will land somewhere. Once E, A, I, O, N, S, T and R have gone in, the shape of the word is usually enough to read the rest, even with half the letters still blank. Write a four-letter word and those same five guesses can return absolutely nothing, which costs the guesser five of their six lives before the game has properly begun.

The practical version: a long word is a puzzle with lots of clues, and a short word is a puzzle with almost none. If you want to win, stop looking for impressive words. The hard hangman words page has the full comparison, with long words measured against short ones side by side.

The hardest hangman words by length

The Wolfram study published its top words broken down by word length, which is the most directly useful part of it for anybody about to set a round. Its picks were mom, jug, gum and phi at three letters; jazz, jinx, lynx and waxy at four; pixie, queue, query and squab at five; and zephyr, syzygy, sphinx and faffed at six.

Two of those are worth a warning before you use them. Squab and faffed will start an argument at most tables, and a word nobody accepts is not a hard word, it is a wasted round. Phi has the same problem in reverse: everybody accepts it and nobody guesses it, which is closer to a trick than a game. Stick to the ones your room would recognize on sight.

40 of the hardest hangman words

Every word below is short, familiar, and built to survive the guesses people actually make. This is the whole bank, measured, so you can pick by the property you want rather than by feel: low distinct-letter counts for a fast kill, empty vowel columns for pure cruelty:

Bookkeeper is the odd one out and it earns its place: ten letters, but only six distinct ones, with three consecutive double letters, which is a thing no other common English word does. It is the only long word on this page, and it is here to prove the rule rather than break it.

Is it fair to use the hardest words?

Only if you say so first. A word like jazz against six wrong guesses is close to unwinnable, and there is no satisfaction in a game the guesser never had a chance in. Announce that this round is a hard one, hand out ten guesses instead of six, and the same word becomes the best round of the evening rather than the one that ended it.

The other honest option is to let the words come from somewhere neither player controls. Half the reason the hardest-word question is interesting at all is that people suspect the setter of stacking it, and a generator that hides the word from everybody makes the suspicion impossible.

Looking for something more winnable?

These 40 are the brutal end of the 710 words in the generator's banks. One step down, the hard hangman words list has 90 that are tough without being cruel, and the good hangman words page has 105 built for a close game. The main hangman words page holds 265 sorted by category.

If you would rather be laughed at than feared, the 90 funny hangman words are chosen for the reveal, and the hangman phrases list plays completely differently, because word gaps hand the guesser information for free. The letter order that beats all of this is on how to play hangman.