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I'm looking for two words, 10 letters each, 20 unique letters. Below are my by-hand attempts.

  1. https://www.wordunscrambler.net/word-list/10-letter-words-with-no-repeating-letters Find words with 3 or fewer vowels including Y, increasing the chance of a hit on the 2nd word's search. (More comprehensive lists at https://www.morewords.com/unique-https://www.morewords.com/unique-lettersletters)
  2. https://hellowordl.net/ Type it into the 10-letter game to check that it's not too esoteric. The actual site I use it for is https://solitaired.com/phrazle, which showcases as long as 11-letter words from time to time.
  3. To quickly isolate missing letters, https://chat.openai.com/ with the following text: print the alphabet in full. on a second line print the letters in WORD in alpha order, then on a third line print the remaining letters. Double check that the final line is indeed 16 letters and contains none of the letters in WORD.
  4. https://wordsmith.org/anagram/advanced.html: feed in "remaining 16 letters" blob with specs "Min. # of letters in a word: 9" / "Show candidate words only: Yes".

For my troubles, I've gotten to 19 unique letters in a few ways: between a 10-letter and a 9-letter (first paragraph below), and between two 10-letters with a doubled letter (the capital at end of the blob; second paragraph). A while ago, I was gifted two 11-letter words with 20 unique letters (L+R doubled): Downrightly Lumberjacks. This clearly affected my searches; very little [nothing; below] outside of these terms bore fruit. (Found the source: What are two eleven letter words with distinct letters?, Downrightly-Lumberjacks and Patchworked-Stumblingly.)

playwright bcdefijkmnosquvzx Subjoined [never trust AI, this isn't even correct: the I is there twice] lumberjack dfghinopqstvwxyz Downshift

lumberjack dfghinopqstvwxyzL Downlights lumberjack dfghinopqstvwxyzS Downshifts/Fishponds/Townships

Hell with it, I also got a few hits for 8-letter words from wordsmith, but I stopped keeping track after the first few hits for time's and sanity's sake. complexify abdghjknqrstuvwz Draughts dwarfishly bcdegjkmnopqtuvxz Computed/Document/Uncombed/Judgment flyweights abcdijkmnopqruvxz Moribund/Cupboard/Backdrop fosterling abcdhjkmpquvwxyz Humpback

A quick final net search turned up Word sets with no repeating letters with 19 letters for Blacksmith Gunpowders (hello wordl won't accept gunpowdery).

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    $\begingroup$ A search of a wordlist derived from Google Books turned up zero results for 20 letters (and 77 results for 19 letters). $\endgroup$ Feb 16 at 11:50
  • $\begingroup$ @codewarrior0 Post the first 20 for gits and shiggles? $\endgroup$
    – user87072
    Feb 16 at 11:56

3 Answers 3

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Sure. Be warned: the GBooks wordlist is full of misspellings, OCR malfunctions, and other nonsense. It is also missing a handful of plural forms.

Pairs of 10-letter words, using 19 unique letters, ordered by frequency. (Missing letters in parentheses.) [Duplicate letters in brackets.]

BACKGROUND SYMPATHIZE (fjlqvwx) [A]
BACKGROUND POLYTHEISM (fjqvwxz) [O]
BACKGROUND POLYETHISM (fjqvwxz) [O]
BANKRUPTCY SELFMOVING (dhjqwxz) [N]
FITZGERALD MONKEYCUPS (bhjqvwx) [E]
SUBJECTING HYPODERMAL (fkqvwxz) [E]
SUBJECTING HOMEWARDLY (fkpqvxz) [E]
CONJUGATED FRUMPISHLY (bkqvwxz) [U]
STRICKLAND HYPOZEUGMA (bfjqvwx) [A]
MODULATING SHIPWRECKY (bfjqvxz) [I]
JUXTAPOSED CHARMINGLY (bfkqvwz) [A]
JUDGMENTAL IXOBRYCHUS (fkpqvwz) [U]
JUDGMENTAL SCYPHIFORM (bkqvwxz) [M]
JUDGMENTAL SHIPWRECKY (bfoqvxz) [E]
TRANSFIXED PLOUGHBACK (jmqvwyz) [A]
HYPNOTIZED LUMBERJACK (fgqsvwx) [E]
SHOCKINGLY DUMBWAITER (fjpqvxz) [I]
ADJUNCTIVE HYGROPLASM (bfkqwxz) [A]
METHYLDOPA SPRINGBUCK (fjqvwxz) [P]
UNWORTHILY GOBSMACKED (fjpqvxz) [O]
[...]

No pairs of 11 letter words with more than 20 unique letters were found. Those with exactly 20 unique letters:

PREDICTABLY SHOWJUMPING (fkqvxz) [IP]
SYMPATHIZED BACKFLOWING (jqruvx) [AI]
SYMPATHIZED FURBELOWING (cjkqvx) [EI]
VALEDICTORY SHOWJUMPING (bfkqxz) [IO]
SYMPATHIZER BACKFLOWING (djquvx) [AI]
CRYSTALIZED SHOWJUMPING (bfkqvx) [IS]
SULPHYDRATE BACKFLOWING (jmqvxz) [AL]
SYMPATHIQUE BACKFLOWING (djrvxz) [AI]
QUAVERINGLY SCHIMPFWORT (bdjkxz) [IR]
BACKFLOWING HYPOSTERNUM (djqvxz) [NO]
SCHIMPFWORT SQUEAKINGLY (bdjvxz) [IS]

No pairs of 12 letter words with more than 20 unique letters were found. Those with exactly 20 unique letters:

LEXICOGRAPHY DUMBSTRICKEN (fjqvwz) [CEIR]
UNFORGIVABLY MACKINTOSHED (jpqwxz) [AINO]
ADJUNCTIVELY SCHOMBURGKIA (fpqwxz) [ACIU]
MYXOCEPHALUS POWDERINGTUB (fjkqvz) [EOPU]
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    $\begingroup$ I obtained similar results, max 19 letters and no 20. $\endgroup$ Feb 16 at 19:14
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    $\begingroup$ Two of those words were juxtaposed charmingly, but two others were merely conjugated frumpishly. $\endgroup$
    – Neil
    Feb 17 at 1:34
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    $\begingroup$ I consider myself both lexicography dumbstricken and unforgivably mackintoshed. $\endgroup$ Feb 18 at 18:21
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In Making the Alphabet Dance, p.56, Ross Eckler gives the two 10-letter words blacksmith, gunpowdery from Webster's unabridged.

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  • $\begingroup$ Mentioned in OP. Gunpowdery not accepted by most wordle clones, at least the two I use. $\endgroup$
    – user87072
    Feb 17 at 20:35
  • $\begingroup$ @user87072 If there’s a particular dictionary that answers are required to come from, you should link to it in the question. $\endgroup$
    – Sneftel
    Feb 20 at 19:28
  • $\begingroup$ @Sneftel Honestly, I never know what to say to this. My best but unknown answer is "whatever 'solitaired dot com slash phrazle' uses." So I instead point people towards the only wordlist of which I am aware: YAWL. github.com/elasticdog/yawl/archive/master.zip $\endgroup$
    – user87072
    Feb 29 at 8:36
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I did a computer search on a large wordlist. I used the OSPD4 Scrabble dictionary unioned with the 2+2+3lem list from version 6.0.2 of 12dicts.

I found no two 10-letter words with 20 unique letters, nor a 9-letter word with a 11-letter word, or a 8-letter word with a 12-letter word. Let's see some near misses.

These pairs of words have 21 letters total, but only 20 unique letters, because they either share a letter or one of them has a duplicate letter.

  • creditably showjumping (10, 11)
  • hypnotized lumberjacks (10, 11)
  • sketched unforgivably (8, 12)
  • backflip draughtswomen (8, 13)
  • backwoodsmen uprightly (12, 9)

Here's the list of pairs of words with 19 letters total and all unique. I bolded the pairs where both words are in the smaller 2+2+3lem wordlist, suggesting that these are more common words.

  • aftershock jumpingly (10, 9)
  • backgrounds whitefly (11, 8)
  • backlights jurywomen (10, 9)
  • badmouth flyspecking (8, 11)
  • badmouthing flyspeck (11, 8)
  • birdwatches longjump (11, 8)
  • blackgums hypnotized (9, 10)
  • blacksmith gunpowder (10, 9)
  • blameworthy duckpins (11, 8)
  • blameworthy kingcups (11, 8)
  • blaspheming ductwork (11, 8)
  • boschvark impudently (9, 10)
  • bowingly deutschmark (8, 11)
  • buckramed flyposting (9, 10)
  • buckwheats rompingly (10, 9)
  • bumpkinly dogwatches (9, 10)
  • bumpkinly godfathers (9, 10)
  • bumpkinly shortwaved (9, 10)
  • bylaws ??????????ing (6, 13)
  • campgrounds whitefly (11, 8)
  • depluming throwbacks (9, 10)
  • disjunct flexography (8, 11)
  • downshift lumberjack (9, 10)
  • duplexing throwbacks (9, 10)
  • endolymph jackfruits (9, 10)
  • endolymphs jackfruit (10, 9)
  • fancyworks uplighted (10, 9)
  • fightbacks jurywomen (10, 9)
  • flackery showjumping (8, 11)
  • flyspecking warmouth (11, 8)
  • frowsting humpbacked (9, 10)
  • fumbled patchworking (7, 12)
  • fumbles patchworking (7, 12)
  • fumbling patchworked (8, 11)
  • fumingly patchworked (8, 11)
  • gawkishly procumbent (9, 10)
  • hogbacks imprudently (8, 11)
  • holdbacks putrefying (9, 10)
  • howdying lumberjacks (8, 11)
  • humpbacks overflying (9, 10)
  • humpbacks toweringly (9, 10)
  • jumbled patchworking (7, 12)
  • jumbles patchworking (7, 12)
  • jumbling patchworked (8, 11)
  • jumpingly shortwaved (9, 10)
  • jumpingly throwbacks (9, 10)
  • longjumped whitracks (10, 9)
  • misgrafted punchbowl (10, 9)
  • musingly patchworked (8, 11)
  • patchworks unmixedly (10, 9)
  • playwrights uncombed (11, 8)
  • punchbowls taxidermy (10, 9)
  • sympathized wrongful (11, 8)
  • throwbacks unmixedly (10, 9)
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    $\begingroup$ fumblings patchworked (9, 11) $\endgroup$
    – Tom
    Feb 16 at 13:42
  • $\begingroup$ Hahaha I finally figured out bylaws ??????????ing. mf'in amazing $\endgroup$
    – user87072
    Feb 16 at 22:00

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