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This is a challenge for word-puzzle lovers. It might be a bit more of a game than a puzzle, but I think it is not limitless in it's answers, so a final answer could be found (eventually).

What is the longest list of growing anagrams which can be put into a grammatically correct English sentence?

Example for clarification:
 Start with a word and then add words to the list with each having one additional letter to the one before. All letters may be re-arranged, i.e. all anagrams of the word are allowed.

I
in
pin ( or alternatively: nip )
pain ( or alternatively: pian )
paint (or alternatively: inapt )
...

You may add any letter, but the list is only valid if you can then put all words of it into a single, English sentence which is grammatically correct. (It does not have to be very meaningful.)
Such as in:

I paint "pin" in pain!
...says the painter while he is painting a shop-name ( "Pin & Needle" ) onto the wall while having severe backache...

So, the aim is: Find a single sentence using all (and only) the words of such a list, i.e. each word-length appears exactly once.

Rules:

  • Diacritics may be handled as "group" represented by their simplest form ( a, ä, á... = a ) to allow for more flexibility in the solutions.

  • The shortest word of the list may have any length. (It does not have to be a single letter.) But the list has to contain a single word for each 'length' between the shortest and the longest word.

  • You may use arbitrary punctuation in the sentence. (Compound words count as single word.)

  • Names and acronyms are allowed but if used, give a reference for their validity.

  • If the meaning of the sentence is not apparently clear, give a little example of where it could be appear. (See example above.)

  • All words of the list have to appear exactly once in the sentence.

Bonus:
This puzzle is about English, but if you can do the same in any other language and have a good example, please post here also. It will not be accepted as answer, though.

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    $\begingroup$ This is a bit confusing. I thought at first that each word had to be an anagram, so I was going to ask what ni meant! :-) $\endgroup$
    – h34
    Commented Jan 6, 2015 at 17:51
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    $\begingroup$ The way these are turning out, they could be puzzles! You're given the paraphrase and need to figure out the growing anagram sentence. $\endgroup$
    – xnor
    Commented Jan 8, 2015 at 18:13
  • $\begingroup$ And I have my 13 word solution added. :) $\endgroup$
    – thepace
    Commented Jan 9, 2015 at 8:31
  • $\begingroup$ Or you could be given the longest word and have to work down to a word with one letter. I've just posted a 14-worder BTW :-) $\endgroup$
    – h34
    Commented Jan 9, 2015 at 19:22
  • 3
    $\begingroup$ I’m voting to close this question because open-ended puzzles are off-topic as of May 2019 $\endgroup$
    – bobble
    Commented Aug 5, 2021 at 3:55

19 Answers 19

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46
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16 Words (Internationalize)

I
iN
Tin
tinE
ineRt
retAin
reLiant
retainAl
alienatOr
orientalIa
rationaliZe
Nationalizer
lineArization
relatInization
interNalization
intErnationalize

Sentence

I, reliant nationalizer, retain internalization; internationalize orientalia relatinization; rationalize linearization retainal; tine inert alienator in tin.

Explanation:

I (being a trustworthy nationalizer) hold on to incorporation; internationalize the process of translating into Latin those books characteristic of the Orient; justify the retention of linearization; and enclose (tine) a dormant ostracizer in metal.

I can assert with reasonable certainty that no longer chain exists (according to the dictionary that I am using to generate this). There are a huge number of variations of the chain starting with

"Internationalize",

but this one was possible to squeeze a grammatical sentence out of.

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3
  • $\begingroup$ If anyone can add "internationalizes/internationalizer"-->"internationalizers" to this chain, 18 is within reach. Not sure whether this is achievable though. I wouldn't think it would be a separate chain, but if you come up with one, feel free to comment it. $\endgroup$
    – archaephyrryx
    Commented Jun 5, 2016 at 19:53
  • $\begingroup$ Along the lines suggested in your first comment: I, reliant nationalizer, retain internalization alienator internationalizes; internationalize orientalia relatinization; rationalize linearization retainal; inter tin tine in internationalizers. $\endgroup$
    – Peter LeFanu Lumsdaine
    Commented May 25, 2018 at 10:58
  • $\begingroup$ “I, a trustworthy nationaliser, hold onto incorporation (which the ostraciser is trying to internationalise); internationalize the process of translating artefacts of the Orient into Latin; justify the retention of linearization; and stab my opposers with a fork (bury a prong in them).” $\endgroup$
    – Peter LeFanu Lumsdaine
    Commented May 25, 2018 at 11:02
80
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Twelve words:

a nearsighted ant sergeant negates an agent, denigrates estranged straightened gnat agents

a
an
ant
gnat
agent
agents
negates
sergeant
estranged
denigrates
nearsighted
straightened

An officer in an army of earthbound insects, suffering from poor eyesight, orders an informer to be dispensed with, and is harshly critical of an ex-couple of flying insect infiltrators, both graduates of a course to eliminate unwanted bodily bends.

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    $\begingroup$ I accept this for now as the longest, but no guarantee it isn't taken back if a longer, valid answer arrives... $\endgroup$
    – BmyGuest
    Commented Jan 8, 2015 at 15:03
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    $\begingroup$ (+1): this is by far the most understandable sentence made. $\endgroup$
    – Mr Pie
    Commented Apr 26, 2019 at 1:20
30
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Nikola Tesla, decrepit in old age, aggrieved by ailments, but still doing his experiments causing filaments (as in a light bulb) to explode.

A lamest Tesla sat at last - laments ailments, fulminates filaments. (10 words)

In a post-apocalyptic world, farm animal meat is a thing of the past. To retain its customers, driven away by ever-increasing prices and a bland product, one delicatessen put up this window sign:

Later, a saltier rat at earliest retail rate. (8 words)

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28
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Thirteen words:

13 Universalists
12 Universalist
11 Antiviruses
10 Intrusives
9  Intrusive
8  Inviters
7  Inverts
6  Strive
5  Rivet
4  Tire
3  Tie
2  It
1  I

Slightly contrived sentence:

Universalists rivet intrusive antiviruses, inviters tie intrusives (inverts it), I tire; Strive, Universalist!

Translation:

Those seeking a universal approach to computing will package their operating systems, somewhat firmly, with annoying security software. Those who would invite trouble choose to disable these annoyances, thus reversing the intended antiviral effect. I become bored with this state of affairs, and say to those operating system manufacturers: "Keep trying!".

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  • $\begingroup$ Yep. Valid and longest answer to date. Well, done. $\endgroup$
    – BmyGuest
    Commented Jan 9, 2015 at 12:25
  • $\begingroup$ too true, friend. too true. :{ $\endgroup$
    – Nyk 232
    Commented Jul 7, 2015 at 19:26
27
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Fourteen words:

"Presentational toenail replantations entail senatorial alterations rationale", leant a relation, late, at alternations tea.

a
at
tea
late
leant
entail
toenail
relation
rationale
senatorial
alterations
alternations
replantations
presentational

A family member, at an afternoon event held to celebrate the swapovers (of a kind which we will not reveal), tardily swayed over and offered a rather silly phrase - a phrase alleging that operations to reverse cosmetic surgery to toenails would produce a credible reason for changing the holders of political office.

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    $\begingroup$ It's a stretch, but you could use the quasi-word "anti-prolateners" (people who are against that which makes more prolate) as a bridge to "representational". $\endgroup$
    – Matt Malone
    Commented Jan 9, 2015 at 20:51
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    $\begingroup$ That's a surprisingly coherent sentence given the circumstances. Bravo! $\endgroup$
    – xnor
    Commented Jan 11, 2015 at 4:10
23
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12 in ascending order of length

I, in tin unit, unite minute pinetum, tumpline, penultima; manipulate planetarium planetariums

I, in a metal shed, combine a very small coniferous arboretum, a load-carrying strap and a logic game, and handle models of the solar system in a building made for such a model

I

in

tin

unit

unite

minute

pinetum

tumpline

penultima

manipulate

planetarium

planetariums

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2
  • $\begingroup$ This is really good. Wow. $\endgroup$
    – Anubian Noob
    Commented Jan 9, 2015 at 3:26
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    $\begingroup$ The ascending word order is a bonus +1 (but not required). Nice sentence. $\endgroup$
    – BmyGuest
    Commented Jan 9, 2015 at 12:39
14
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Starting staring in startling sin, I sing Sting string.

Beginning to gaze with shocking immorality, I sing a line from (the musician) Sting.

These are nine words, and no anagramming is needing. They letters stay in the same order when letters are added.

i
in
sin
sing
sting
string
staring
starting
startling

I didn't invent this sequence; I read it somewhere but I don't remember where.

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    $\begingroup$ Really? D@rn. Then the puzzle is less original than I thought. (Had the idea today while walking through some woods...) $\endgroup$
    – BmyGuest
    Commented Jan 6, 2015 at 20:05
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    $\begingroup$ @BmyGuest This is from a slightly different challenge - you're allowed to insert the new character anywhere in the previous word, but you can't rearrange any of the other letters. $\endgroup$
    – Aaron Dufour
    Commented Jan 7, 2015 at 14:20
14
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4:

13 Letter (Rhinoplasties)
a <1>
in<2>
its<3>
nose<4>
noses<5>
inters<6>
nostril<7>
hospital<8>
hospitals<9>
paltriness<10>
hospitalise<11>
relationship<12>
rhinoplasties<13>

Rhinoplasties: nostril inters its paltriness ; a nose hospital relationship; hospitalise noses in hospitals

And yes its a hyperbole with descriptions about what rhinoplasties meant. Its how a nose buries its worthlessness. Its a relationship of a noses and hospitals. It also means that you hospitalise your nose in a hosptial. Loving it :)

3:

a seat at east (EAST)
Was a waste at west (WEST)
o! not horn or thorn (NORTH)
o! hot to oust south (SOUTH)

2:

Its rest I resist; it tires

(and yes its a lie) :-)

1:

I tried, I retried, I retired :)

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    $\begingroup$ Nice anagrams, but your shortest word is "I" and there are now words with 2,3,4 letters. So it is not a valid list, I'm afraid. Nice statement, though. $\endgroup$
    – BmyGuest
    Commented Jan 6, 2015 at 18:08
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    $\begingroup$ missed it... will retry before retiring. $\endgroup$
    – thepace
    Commented Jan 6, 2015 at 18:16
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    $\begingroup$ First one sounds like abuse of sleeping pills. $\endgroup$
    – Joshua
    Commented Jan 6, 2015 at 18:36
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    $\begingroup$ +1 for the 3rd one. Not the longest, but so nicely themed! Love it. $\endgroup$
    – BmyGuest
    Commented Jan 7, 2015 at 22:40
  • $\begingroup$ I've got a 10 based on the words in your answer 1 - I can give the whole thing or some hints first if you like. $\endgroup$
    – Chris H
    Commented Jan 8, 2015 at 13:41
13
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Nine words:

“Straying giants stang an ant staying stingrays" - a gnat.

Meaning: a flying insect reports that wandering abnormally large individuals used nettle leaves to inflict pain on an earthbound insect engaged in serving legal notices on fish.

Which is surreal, but not as neat as the five-word version it sprang from:

An ant stang a gnat.

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11
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A short, random attempt. 6 words.

This Sith's thesis? I hit it.

Useful for when someone asks you if you punched the paper that Darth Maul was supposed to turn in.

Found one with 7 words, but I can't think of how it would be useful.

Sisters tie it; I tire; tires resist.
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    $\begingroup$ That last sentence is useful when you are trying to get nuns to help you put chains on your tires to get through a snowy mountain pass because you are worn out from the effort. $\endgroup$
    – YoungJohn
    Commented Jan 6, 2015 at 18:03
  • $\begingroup$ The first sentence could be used as a reply if you (a Sith) were asked what you think happened to a damaged item during a period in which you had temporary amnesia. $\endgroup$
    – A E
    Commented Jan 6, 2015 at 18:34
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    $\begingroup$ I would say that ? makes that first attempt 2 sentences. $\endgroup$
    – njzk2
    Commented Jan 8, 2015 at 16:24
11
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1 to 11

sand dancers reascend, desecrating a decreasing sedan and an increased sander

1 to 12. The tale of a tough soldier having trouble decorating his clothes, whilst an ex-pat displays videos of his own delightful solutions online.

A mean marine and raiment garnishment nightmares, an emigrant streaming charmingest garnishments

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    $\begingroup$ Like your sand dancers. (Very strictly applying the rules, it would be sand-dancers as one 11 letters word though, wouldn't it?) $\endgroup$
    – BmyGuest
    Commented Jan 9, 2015 at 12:40
  • $\begingroup$ Or "Sand Dancers" (en.wiktionary.org/wiki/Sand_Dancer) meaning people from South Shields, in the vernacular of my home town. $\endgroup$
    – Phil M Jones
    Commented Jan 9, 2015 at 13:00
9
$\begingroup$ 
a
at
ate
late
stale
castle
elastic
elastics
silicates
specialist
plasticised
(deplasticise)
(deplasticiser)
(deplasticisers)

A late silicates specialist ate stale plasticised elastics at elastic castle.

An expert in silicon compounds was staying at an old castle built out of random rubber bands and other stretchy materials when he decided to eat some of the walls. The structure of the castle was stable due to the rubber amalgam, giving it a slightly malleable texture. He is dead now, presumably from eating plasticised rubber... or is it rubberized plastic? Only the builder (and the dead specialist) will ever know.

The last three words don't really count since I couldn't fit them in the sentence, plus the words are recycled and lazy, but oh well!

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  • $\begingroup$ I love the sentence, but you're right:As it is now, it's only an 11. $\endgroup$
    – BmyGuest
    Commented Jan 9, 2015 at 9:09
  • $\begingroup$ I think "A late deplasticised specialist deplasticise castle; ate stale plasticised silicates at elastic elastics." Is valid, although it does not flow too good, and I am a bit unsure about "at elastic elastics". $\endgroup$
    – Taemyr
    Commented Jan 9, 2015 at 12:28
9
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15 14 words:

Teal eat elastics specialist, steal plasticised silicates, deplasticise replasticised elastic, at a preplasticised castle.

(A flock of wild duck go on a generally destructive rampage at an industrial science laboratory.)

A
aT
Eat
teaL
Steal
Castle
elastIc
elasticS
silIcates
sPecialist
plasticiseD
dEplasticise
Replasticised
Preplasticised

Credit: adapted from Psybin’s answer.

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    $\begingroup$ This is 14 words, not 15. $\endgroup$
    – jsh
    Commented Jan 23, 2015 at 13:26
  • $\begingroup$ @jsh: holy crap, you’re right! I guess OP should de-accept this and re-accept h34’s earlier 14-word answer. I guess the error came in because I was initially trying a chain up to “preplasticisers”, but couldn’t quite get something coherent out of that, and then switched to “preplasticised” without fixing my count. $\endgroup$
    – Peter LeFanu Lumsdaine
    Commented Jan 24, 2015 at 12:09
8
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My first attempt with 8 words:

A carnage ran near an arcane canaigre arena.

Meaning "A carnage spread near a mysterious arena where wild rhubarb are pitched in battle". Not very meaningful, but perfectly correct. I could think of this in the intro of a first-person shooter video game.

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  • $\begingroup$ @mdc32 It is not a general requirement to give all anagrams. (It would become boring for long words later.) However, the use of tools such as "wordsmith.org" is very legitimate! $\endgroup$
    – BmyGuest
    Commented Jan 6, 2015 at 17:20
  • $\begingroup$ @BmyGuest Yup, sorry. Read the question wrong at first. $\endgroup$
    – mdc32
    Commented Jan 6, 2015 at 17:20
  • $\begingroup$ @Goto0: +1 if you can find/describe a situation/context in which the sentence would be useful ;c) $\endgroup$
    – BmyGuest
    Commented Jan 6, 2015 at 17:22
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    $\begingroup$ Added canaigre, which I found with this regex dictionary. Very useful for these sorts of puzzles. visca.com/regexdict $\endgroup$
    – Matt Malone
    Commented Jan 6, 2015 at 18:00
8
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I tic it: otic topic, tropic apricot, operatic imprecation, preatomic importance.

Translation:

This is what I involuntarily blurt out: matter dealing with the ear, fruit from low latitudes, very well sung curses, early 20th century significance.

Pretty meaningless, but I got 11 words.

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5
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Only 9 but a bit of a tongue-twister

I sleightly, slightly light sightly slight gilt; it lit.

I cunningly make a small flame on a slim attractive government bond; it alighted

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5
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Update: Maybe 15? These are technically two sentences:

Tie ratiocinated, "Trite, cattier attire contraindicated accreditation." I ratiocinate, "Contraindicate it? Interact! Intricate, antierotic rite tie!"

contraindicated
contraindicate
accreditation
ratiocinated
ratiocinate
antierotic
intricate
interact
cattier
attire
trite
rite
tie
it
I

I and a fellow comissioner Tie are evaluating whether or not to grant accreditation to a school. The school's principal is a highly eccentric lady who stands on bizarre ceremony. Tie explains to me that he wished to refuse to grant accreditation to the school on account of the inappropriate slogans printed on the principal's T-shirt. I counter that had Tie actually interacted with the principal, he would have discovered that her behaviors were an equally good reason to deny accreditation.

Old answer:

My best is only 9 so far.

o
do
rod
cord
crowd
crowds
scowder
escrowed
scowdered

O escrowed rod, scowdered crowds do crowd scowder cord.

Translation: A rod of gold is held in escrow in a large metal safe. Thieves are attempting to blow up the safe with dynamite, but they crowd the fuse and become scorched. The owner of the safe cries out with glee to the rod of gold: "O escrowed rod, scowdered crowds do crowd scowder-cord!"

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  • $\begingroup$ Very nice indeed, and you get a +1 from me, but for the technical reason you've mentioned yourself (not a single sentence), I'll not accept it as answer. $\endgroup$
    – BmyGuest
    Commented Jan 16, 2015 at 7:54
3
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I couldn't resist one-upping...

Fifteen words:

15 classifications
14 classification
13 salifications
12 laicisations
11 laicisation          
10 antisocial
9  scalation            
8  santalic         
7  satanic
6  antics
5  saint
4  anti
3  tan
2  an
1  a

Sentence:

"Anti saint laicisations classification (laicisation antics classifications) — satanic salifications, a santalic scalation (an antisocial tan)."

Translation:

"What follows is a description of anti-Christian attempts at secularisation (i.e. descriptions of the foolish behaviour involved in secularisation) — evil applications of salt, applying a protective skin the colour of sandalwood (all of which refers to an offensive fake tan)."

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  • $\begingroup$ Very nice. But isn't it just a title and not a sentence - i.e. missing a verb? $\endgroup$
    – BmyGuest
    Commented Jan 12, 2015 at 16:13
  • $\begingroup$ Yes, probably true. $\endgroup$
    – jsh
    Commented Jan 23, 2015 at 13:27
1
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6 words:

I  
if  
fin  
fins  
sniff  
sniffs

If I sniff fins, fin sniffs.

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  • $\begingroup$ Is "fin" used as a name "Fin" here? $\endgroup$
    – BmyGuest
    Commented Jan 9, 2015 at 12:36
  • $\begingroup$ Could be a Finnish national. Or does that involve more 'n's? $\endgroup$
    – A E
    Commented Jan 9, 2015 at 13:01

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