When English speakers talk about someone having a “devil-may-care” life or lifestyle, they are referring to the idea of being uncaring or generally willing to take risks. This idiomatic phrase is used in different ways; for example, someone might be said to have a “devil-may-care” attitude or outlook on life. People may even refer to “devil-may-care” professions like that of a professional stuntsman.
The phrase “devil-may-care” seems to have originated around the 1800s. Other common phrases of that time also featured the word “devil,” which in some English speaking cultures and communities represents one of many demonic entities, and in others, is used with a capital letter to indicate the primary “Devil” of Judeochristian religion. The phrase also mirrors others in societies speaking other languages, for example, in German, where the use of the word “Teufel” or “Topfel” features prominently in many idiomatic phrases.
As for the origin and meaning of “devil-may-care,” it seems that the phrase stands as a sort of general antithesis to the speaker’s own outlook. Here, the phrase may have originated as part of a longer phrase; some cite examples like “The devil may care; I certainly don’t.” The phrase is also similar to another that uses a rather similar idea: when English speakers say “devil take the hindmost,” the idea is that no one wants to be last. For example, when someone says “They took to the street, away from the scene of the fire, devil take the hindmost,” the idea is that everyone ran away quickly, not wanting to be left behind.
In some cases, the use of “devil-may-care” may relate to the idea of “devilish” or “impish” glee. This sort of phrase describes someone with a sly or slightly malevolent streak to their humor. Usually, it does not mean that the subject is actually evil or about to do evil things. Rather, devilish or impish glee is generally recognized as a mischievous yet playful demeanor.
The use of phrases like “devil-may-care” shows how obsessed past English speaking cultures were with the idea of a devil. Dozens of idioms exist in the English language featuring this persona. and all that its collective image entails. Phrases like “devil take you” or “to the devil” mostly achieved prominence in earlier centuries, where modern English speakers are less likely to invoke this type of character reference.