Cryptic crossword clue
One might fly with trendy impoverished playwright 12

The most common and most likely answer to this crossword clue is the 12 letter word WHIPPOORWILL

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Buddy explains!

The straight part
We know that "One might fly" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case one might fly = whippoorwill.
The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.
This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.

What does WHIPPOORWILL mean?

WHIPPOORWILL noun
  1. A nocturnal insectivorous bird of North America, Caprimulgus vociferus, a type of nightjar, named after its characteristic call.

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