I seem to see the phrase "shake his booty" being used to say something is good and attractive. But does it mean "shake his butt"? And if they are the same, why does "shake his butt" seem a somewhat distasteful action, but "shake his booty" all of a sudden becomes somewhat glamorous?
Learn English – Does “shake his booty” mean “shake his butt”? And does it make it more attractive
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It means roughly: "it is unlikely that I should be lucky enough for this to happen, but if it did I would be great."
See Wiktionary.
--- UPDATE ---
As a follow up to why it means that, here is my speculation. It is a simple figure of speech that over time has formed into an idiom. In this case "chance" is used by metonymy to mean the results of chance. The literal meaning would be "If the unlikely event happens". Here an aspect of the event -- its low probability -- is used by metonymy for the event as a whole. If you remove the figure of speech the expression would be "[If] the unlikely event happens, [it] would be a fine thing." The "unlikely event happens" is replaced by metonymy with the word "chance", and we get the original.
After this substitution there are various elements and baggage that attach to the phrase over time to give it the current color of meaning, specifically the strong pessimistic tone, and various ellipses to make the saying pithy.
OED has a draft entry from 2010:
Chiefly Brit. on (also off) the back of : on the basis of; by capitalizing on the work or success of.
1906 Baily's Mag. Jan. 30/2 On the back of every successful form of enterprise kindred ventures are too often floated without much regard to the question of whether they contain the elements of success.
...
1993 Accountancy Oct. 49/1 Off the back of its tea business Moran diversified into freight.
2004 H. Kennedy Just Law (2005) xiii. 278 The government wins support for the entitlement card on the back of asylum scares.
I suppose it may come from horse-riding, referring either to riding on, or jumping off from, the back of an animal.
Image c 1875 | Source | Copyright Library of Congress
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Best Answer
"Neither is glamorous! "Booty" is American slang for buttocks but almost universally refers to that of a woman. "Butt" is also slang for "buttocks" but does not imply gender. Moreover, "booty" has overt sexual overtones (and is, in fact, slang for having sex in some cases), whereas "butt" is not. (A parent might refer to his/her child's butt, but never the child's booty.) You may be hearing the term "booty" in pop music lyrics or even some forms of pop journalism, but it is not considered a professional, polite, or glamorous word.
As far as I know, the origin of the term is int he term for a pirate's treasure, called his "booty". The metaphoric link is to a woman's "treasure", I think.