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For those of us who enjoy wordplay, Mark Dominus' blog post about the best english language anagram is great fun.
A few years ago I mentioned in passing that in the 1990s I had constructed a listing of all the anagrams in Webster's Second International dictionary. (The Webster's headword list was available online.)
[...] The list starts with aal ala and ends with zolotink zolotnik which exemplify the problems with this simple approach: many of the 46,351 anagrams are obvious, uninteresting or even trivial. There must be good ones in the list, but how to find them?
I looked in the list to find the longest anagrams, but they were also disappointing: cholecystoduodenostomy duodenocholecystostomy
[...] This example made clear at least one of the problems with boring anagrams: it's not that they are too short, it's that they are too simple. Cholecystoduodenostomy and duodenocholecystostomy are 22 letters long, but the anagrammatic relation between them is obvious[.]
This gave me the idea to score a pair of anagrams according to how many chunks one had to be cut into in order to rearrange it to make the other one. On this plan, the "cholecystoduodenostomy / duodenocholecystostomy" pair would score 3, just barely above the minimum possible score of 2. Something even a tiny bit more interesting, say "abler / blare" would score higher, in this case 4. Even if this strategy didn't lead me directly to the most interesting anagrams, it would be a big step in the right direction, allowing me to eliminate the least interesting.
The method and results are laid out in the source post.
For those who don't wish to read the source post, his best pairing is cinematographer megachiropteran.
-- submitted from IRC
(Score: 2) by PiMuNu on Thursday February 23 2017, @09:56AM
... a couple of completely different scoring algorithms are "how common are the words" (e.g. skim many documents and look to see what sort of words come up) and "are the words related" (e.g. skim many documents and look for commonality between different words to train a neural network). He hints at both algorithms in TFA.
So, for example, words that are commonly used, related in a (hopefully) amusing way, and require a complicated rearrangement are likely to be entertaining. Commonly, one also sees anagrams that include multiple words in the initial state and one word in the final state.