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Where does this expression come from?

I understand when it's used, but I was wondering about its origin.

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I've only heard "Pretty please with a cherry on top" –  neil Jun 25 '11 at 17:50
Obviously you've never seen Pulp Fiction, then :) –  Tim Pietzcker Jun 28 '11 at 9:43

3 Answers 3

up vote 7 down vote accepted

According to The Word Detective:

The earliest citation in the Oxford English Dictionary for “pretty please” is from 1913, and the earliest for “pretty please with sugar on top” is from 1973. But my guess is that “with sugar on top” actually arose much earlier, at least by the 1950s. While sprinkling sugar on food has a long history, it was in the 1950s when ready-made sugar-coated breakfast cereal became popular, and the phrase may have been spawned then in imitation of advertising (“Ask Mom for Choco-Balls — the ones with with sugar on top!”) for such wholesome fare.

If you're a word lover, the whole article is well worth reading.

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I can attest that "pretty please with sugar on top" goes back to the 60s, at least. (And I doubt that it has anything to do with sugar-coated breakfast cereal.) –  Hot Licks Oct 4 at 13:17

I found a use of the phrase in The Sun of New London, Connecticut, January 13, 1917:

"pretty please with sugar" image

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How much do you want to bet that the sugar on top is to make it sweeter? –  Kit Z. Fox Jun 28 '11 at 2:49

Just watched a Twilight Zone (Season 3, Episode 17) where the teacher character said "pretty please with sugar on it" .. That from the 1960s and is the earliest popular media reference to the phrase I've heard.

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