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Fokkerdr1 wrote:

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A bit of history first: the original expression, of course, was I couldn't care less, meaning "it is impossible for me to have less interest or concern in this matter, since I am already utterly indifferent". It is originally British. The first record of it in print I know of is in 1946, as the title of a book by Anthony Phelps, recording his experiences in Air Transport Auxiliary during World War II. By then it had clearly become sufficiently well known that he could rely on its being recognised. It seems to have reached the US some time in the 1950s and to have become popular in the latter part of that decade. The inverted form I could care less was coined in the US and is found only there. It may have begun to be used in the early 1960s, though it turns up in a written form only in 1966.

Why it lost its negative has been much discussed. It's clear that the process is different from the shift in meaning that took place with cheap at half the price. In that case, the inversion was due to a mistaken interpretation of its meaning, as has happened, for example, with beg the question.

In these cases people have tried to apply logic, and it has failed them. Attempts to be logical about I could care less also fail. Taken literally, if one could care less, then one must care at least a little, which is obviously the opposite of what is meant. It is so clearly logical nonsense that to condemn it for being so (as some commentators have done) misses the point. The intent is obviously sarcastic - the speaker is really saying, "As if there was something in the world that I care less about".

However, this doesn't explain how it came about in the first place. Something caused the negative to vanish even while the original form of the expression was still very much in vogue and available for comparison. Stephen Pinker, in The Language Instinct, points out that the pattern of intonation in the two versions is very different.

There's a close link between the stress pattern of I could care less and the kind that appears in certain sarcastic or self-deprecatory phrases that are associated with the Yiddish heritage and (especially) New York Jewish speech. Perhaps the best known is I should be so lucky!, in which the real sense is often "I have no hope of being so lucky", a closely similar stress pattern with the same sarcastic inversion of meaning. There's no evidence to suggest that I could care less came directly from Yiddish, but the similarity is suggestive. There are other American expressions that have a similar sarcastic inversion of apparent sense, such as Tell me about it!, which usually means "Don't tell me about it, because I know all about it already". These may come from similar sources.

So it's actually a very interesting linguistic development. But it is still regarded as slangy, and also has some social class stigma attached. And because it is hard to be sarcastic in writing, it loses its force when put on paper and just ends up looking stupid. In such cases, the older form, while still rather colloquial, at least will communicate your meaning - at least to those who really could care less.

OK SO WHERE IS S20 GOING TO BE?