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I have listened to Americans say the phrase "I could care less" and it clearly appears to be derived from the original phrase "I could not care less". The original phrase has a logical underpinning, in as much as it states that the level of care being directed to something is so small that you literally could not care less. The American version appears to be an artifact from repetition of an uncorrected error. An error that is so illogical regarding its statement and application that at some point some astute American man/woman of letters must've commented on it and so, reveal the period that its odd and illogical acceptance in to American vernacular came about.

Meehawl
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    Can you identify a single word in English which is not the result of mispronouncing another word or phrase? – Hot Licks Jul 03 '16 at 13:36
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    As I recall it was Friday, February 3, 1973. My late urologist, an otherwise extremely erudite and internationally acclaimed physician, misused the phrase, resulting in the subsequent decline of the English language in general here in America. – Mark Hubbard Jul 03 '16 at 13:59
  • I've always assumed it to be a shortening of a phrase I sometimes use; 'I could care less, but now much'. – Spagirl Jul 03 '16 at 21:25
  • @MarkHubbard -- I'll bet you were pissed. – Hot Licks Jul 04 '16 at 00:07
  • Ha! Urology jokes. Ah wow. Soooo funny. Ah whee. Yeah great. Oh let me sit down. – candied_orange Jul 04 '16 at 01:30
  • Plenty of Americans still say this correctly. – tchrist Jul 04 '16 at 01:53
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    I could care less. [Personally, I feel we Americans are lazy, and the opportunity of simply losing a word to save a few millicalories of effort was a no-brainer, literally.] – Stu W Jul 04 '16 at 03:24

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This is not an American version. It is a sarcastic version. The problem comes from the "not" free phrase never being used in anything other than in a sarcastic way. No one ever sincerely says, "Thank you. This is important to me. I could care less." Even though logically it's positive it has a strong negative connotation. That's why some people don't even think of it as sarcasm, they learn it by rote and ignore the logic. See also, double negatives.

Once you understand the logic and sarcasm it's easy to see. If you don't then it's not.

candied_orange
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  • I've heard the sarcasm explanation given before and it falls short purely because there is no sarcasm in the revised phrase which is why requests to reveal it always go unfulfilled. This also shows up a strange revision of the definition of sarcasm which is another subject entirely. If there is a belief that a sarcastic statement is being made with that phrase then I should probably ask a question regarding how the idea that there is something sarcastic going on came to be. – Meehawl Jul 03 '16 at 14:18
  • @Meehawl Interpret sarcasm to mean mocking here. The phrasing means something along the lines of I could care less, but it's difficult to see how. – deadrat Jul 04 '16 at 01:07
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    I have never believed that story. It seems to madey-uppy. – tchrist Jul 04 '16 at 01:52