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I want to know about the origin of the compound adjective devil-may-care:

Cheerful and reckless:
light-hearted, devil-may-care young pilots

All OED has is

The exclamation devil may care! used as an attribute.

And etymonline.com says:

1837 (but suggested in other forms by 1793).

The earliest relevant result that I could find on Google Books was from 1823, and it was used there as an exclamation:

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So where did this exclamation come from?

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According to the following source the origin may date back to the beginning of the 18th century. It’s actually a shortened idiom. The entire idiom is, “The devil may care, but I do not.” The expression appears to have had the same meaning from its earliest usages:

  • A number of dictionaries state that the first published use of the expression was 1837 however none of them provided a source to support the claim. Idiomation, however, found it in “The Pickwick Papers” by Charles Dickens and published in 1837. Chapter 29 opens with this paragraph:

    • In an old abbey town, down in this part of the country, a long, long while ago–so long, that the story must be a true one, because our great-grandfathers implicitly believed it — there officiated as sexton and grave-digger in the churchyard, one Gabriel Grub. It by no means follows that because a man is a sexton, and constantly surrounded by the emblems of mortality, therefore he should be a morose and melancholy man; your undertakers are the merriest fellows in the world; and I once had the honour of being on intimate terms with a mute, who in private life, and off duty, was as comical and jocose a little fellow as ever chirped out a devil-may-care song, without a hitch in his memory, or drained off a good stiff glass without stopping for breath.
  • It’s doubtful, however, that Charles Dickens was the first to coin the expression as it also appeared in “The Warwickshire Hunt from 1795 to 1836” written by an author known only as Venator, and published in 1837 as well. In the prefatory remarks, the following is found:

    • This is the sort of witchering, not easily defined — but, by its votaries, pretty sensibly felt, in hunting the fox. The light-hearted high-spirited stripling, when cigaring it careless to cover, with a kind of a knowing demi-devil-may-care twist of his beaver, receives in his transit a benison from every real friend of the chase he may chance to pass; and the airy, eager zeal of the youthful aspirant to rolls, tu blues, and the brush, will flush his memory with the frolic gayety of other days, and animate his mind with reflections most welcome to his heart.
  • Philip Morin Freneau (2 January 1752 – 1832) wrote his poem “The Expedition of Timothy Taurus, Astrologer” in 1775. One of the verses includes the idiom as follows:

    • Then the soldier went out, to refresh at the inn —
      Perhaps he did not — if he did it’s no sin —
      he made his congee, and he bowed to us all,
      And said he was going to Liberty Hall:
      ‘Tis certain he went, but certainly where
      I cannot inform, and the devil may care.
  • That the thought wasn’t finished is immaterial as the implication is that the speaker in this poem does not care. Of note as well is the fact that the expression is used with the knowledge that readers understand what is meant by the author,

  • Idiomation believes the expression reaches back at least another 2 generations, to the 1720s. This is based on Idiomation’s suspicions that the spirit of the idiom is a result of the Golden Age of Piracy (1715 – 1725) where on the High Seas pirates recklessly went about their business with no worry or concern as to any consequences resulting from their actions. The only being that might care about their actions would be, of course, the Devil hence the expression.

From (idiomation.wordpress.com)

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