If you guessed Pneumonoultramicroscopicsilicovolcanoconiosis (a disease, silicosis) or Supercalifragilisticexpialidocious (a contrived word introduced in the musical and film Mary Poppins) you are wrong. Think shorter — way shorter. It will help if we clarify that by “complicated,” we mean having many different aspects, or more precisely, definitions. If you have the time, you can thumb through a dictionary, like the authoritative Oxford English Dictionary (OED), where you will eventually run across the lexical rascal. By the way, there was a clue in that sentence.
The most complicated word in the English language is “run.” The word “run” is a real Olympian with more than 715 different meanings. As a noun, “run” has more than 70 unique definitions, while as a verb, the word has 645 different meanings. In the printed second edition of the OED, the definitions of “run” run 63 columns across 21 full pages, which took a lexicographer more than nine months to complete. Perhaps he ran out of time…
The OED begins with these definitions of ‘run’ as a verb with the following citations:
(1) To move the legs quickly so as to go at a faster pace than walking.
A hundred… men ready to run
(2) To go about freely free without being restrained or checked in any way.
We are resolved… not to let them run about as they like.
(3) To hasten to some end or object, or to do something.
The people… run almost from all places to assist his cause.
(4) To retire or retreat rapidly, to take flight.
He… had been forced to cut and run.
(5) To rush at, or, or upon a person with hostile intention.
He ran at me and kicked me.
In an interview with NPR, Simon Winchester, author of The Professor and the Madman: A Tale of Murder, Insanity and the Making of the Oxford English Dictionary, elaborates on the complexity of “run” and the runners-up to the words with the most definitions in the English language:
“When they prepared the first edition of the OED, which took them 70 years to do, so they began this in 1857 and finished – the first edition was published in 1928 – the longest word then or the one with the most definitions was another three-letter word. It was the word ‘set’… it occupies 32 full pages, 75 columns with about 200 meanings… Well, during the 20th century, that word was displaced by another rather similar word, which was the word ‘put.’… But when the OED got around to working on the letter R, which they began working on about two years ago , and got towards the end of R and started looking at words beginning with R-U, it became rapidly apparent that ‘run’ completely outran… both ‘put’ and ‘set.’ And when [the 2011 update to the online edition of the OED] was finished… Peter Gilliver [a lexicographer on the OED team] counted out — just for the verb alone — 645 different meanings. So it’s the absolute champion. So the order is: run, put, set.”
Winchester seems to think that the unique senses of run exploded after the Industrial Revolution, when all sorts of inventions (eg, machines, and eventually computers and digital devices, etc.) that run were introduced.
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For further reading: http://www.npr.org/2011/05/30/136796448/has-run-run-amok-it-has-645-meanings-so-far