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Ann Landers on "could care less" (1960)

We've seen cites for "could care less" from 1955 and 1957, thanks to Proquest (1). Newspaperarchives.com doesn't seem to beat those, but it does have this tidbit, from Ann Landers' syndicated column published in several papers on October 20, 1960:
DEAR ANN: My girl friend and I are having an argument. You know that common expression: "I couldn't care less." Well she says it's "I COULD care less." Please tell us in your column which is right. TOOTH AND TOENAIL

DEAR TOENAIL: The expression as I understand it is "I couldn't care less" which means I don't care at all. On the other hand, maybe she COULD care less, which means she does care at least a little. To be honest, this is a waste of valuable newspaper space and I
couldn't care less.
The earliest cite for "could care less" on the archive is from a Jan.
1957 wire story published in a few papers, about a gray whale that wasgiven a tranquilizer shot in the interest of heart research:

Researchers believe the whale is getting back to normal now, but for a while Sunday the old boy was probably the most happy and who-could-care-less mammal in the seven seas.
I don't think I've seen that usage before "who-could-care-less" meaning "carefree" or "devil-may-care".
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Top answer

[nq:1]We've seen cites for "could care less" from 1955 and 1957, thanks to Proquest (1). com doesn't seem to beat ... and who-could-care-less mammal in the seven seas.

  • [nq:1]We've seen cites for "could care less" from 1955 and 1957, thanks to Proquest (1).
  • com doesn't seem to beat ...
  • and who-could-care-less mammal in the seven seas.
  • " I'm sure if you had ***'s search engine, you could find examples of the string "I could care less" a lot earlier than 1957.
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3 Answers
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[nq:1]We've seen cites for "could care less" from 1955 and 1957, thanks to Proquest (1). Newspaperarchives.com doesn't seem to beat ... and who-could-care-less mammal in the seven seas. I don't think I've seen that usage before "who-could-care-less" meaning "carefree" or "devil-may-care".[/nq]
But it means pretty much the opposite of "I could care less." "Who could care less?" is a rhetorical
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[nq:2]The earliest cite for "could care less" on the archive ... I've seen that usage before "who-could-care-less" meaning "carefree" or "devil-may-care".[/nq]
[nq:1]But it means pretty much the opposite of "I could care less." "Who could care less?" is a rhetorical question with the intended answer, "nobody," and is therefore actually more like "I couldn't care less."[/nq]
Right... it pre
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[nq:1]I'm sure if you had ***'s search engine, you could find examples of the string "I could care less" a lot earlier than 1957.[/nq]
What's happened is that a sarcastic logical comment has been taken as straight up. I'm not sure how to write it out including the colour needed to make "I could care less" make logical sense.

Here's another way of looking at it. Every single vote that

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