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I've found "enterprise", which is 10 letters long. Does anyone know of any longer words that start and end with the same letter?

That letter doesn't have to be 'e', by the way. It just means that the first and last letter of the word have to be identical.

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15  
"Smiles" has a mile between the S's. (I couldn't resist.) – oosterwal Feb 18 '11 at 22:16
This is the kind of thing you should ask a computer, e.g. with a shell script you could use egrep '^([[:lower:]])[[:lower:]]*\1$' /usr/share/dict/british-english-insane |awk '{ print length(), $0 }' |sort -n to filter and order a wordlist. – donothingsuccessfully Mar 15 at 7:30

6 Answers

up vote 15 down vote accepted
  • achondroplasia - 14
  • breadcrumb - 10
  • cineangiocardiographic - 22
  • deinstitutionalized - 19
  • ethylenediaminetetraacetate - 27
  • flameproof - 10
  • governmentalizing - 17
  • handsbreadth - 12
  • interstimuli - 12
  • (There is no word beginning and ending with J)
  • kinnikinnick - 12
  • lepidopterological - 18
  • mesembryanthemum - 16
  • nondiscrimination - 17
  • obbligato - 9
  • postmastership - 14
  • (There is no word beginning and ending with Q)
  • remanufacturer - 14
  • straightforwardnesses - 21
  • transformationalist - 19
  • unau - 4
  • vav - 3
  • wheelbarrow - 11
  • xerox - 5
  • youthfully - 10
  • zuz - 3 (found on Dictionary.Reference.com and TheFreeDictionary.com, but not in the Oxford dictionary)

Many of these words may not feature in the English dictionary. Some are medical or technical words.

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1  
straightforwardnesses? really??? could you use that in a sentence? – advs89 Feb 18 '11 at 16:02
:) I was wondering the same. However, the question was the longest words and I found these. – Sterex Feb 18 '11 at 16:32
I mean, it seems syntactically correct... I just can't imagine any context where it would make any sense at all. – advs89 Feb 18 '11 at 18:17
2  
@advs89: The thing I find most appealing about your comment is the straightforwardness with which you express your disbelief. – dmckee Feb 18 '11 at 20:54
6  
I can appreciate both advs89's and dmckee's straightforwardnesses. – mgkrebbs Feb 19 '11 at 7:00
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up vote 8 down vote

Supercalifragilisticexpialidocious comes to mind.

Although some might claim the word is a bit artificial. :)

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up vote 4 down vote

What's your definition of "word"? Names of chemical compounds can be of any arbitrary length (and various chemical prefixes both start and end with "e", for example)...

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1  
Shouldn't this be a comment? – advs89 Feb 20 '11 at 4:09
granted, I guess it doesn't really matter on a CW... – advs89 Feb 20 '11 at 4:10
3  
@advs89 -- it's kind of the answer, in fact: under some definitions of "word", a word can be of theoretically infinite length. – Neil Coffey Feb 20 '11 at 4:31
up vote 1 down vote

Naturalisation has 14 letters.

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up vote 1 down vote

straightforwardness: 19 letters
Andrianampoinimerina: 20 letters (if we're counting proper nouns)

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up vote 0 down vote

Here's the output of a quick-and-dirty script that I wrote:

  • abetalipoproteinemia - 20
  • bumblebomb - 10
  • cineangiocardiographic - 22
  • dynamometamorphosed - 19
  • ethylenediaminetetraacetate - 27
  • frictionproof - 13
  • governmentalising - 17
  • hygrothermograph - 16
  • improvvisatori - 14
  • killickinnick - 13
  • labioglossopharyngeal - 21
  • metapostscutellum - 17
  • nonindustrialization - 20
  • overlubricatio - 14
  • plenipotentiaryship - 19
  • qepiq - 5
  • rhomborectangular - 17
  • supercalifragilisticexpialidocious - 34
  • transubstantiationalist - 23
  • uturuncu - 8
  • vav - 3
  • windlestraw - 11
  • xylanthrax - 10
  • youthfullity - 12
  • zizz - 4

I apologise for not being a good citizen and editing the good ones into the main answer.

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protected by RegDwighт♦ Dec 22 '11 at 22:21

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