The original idea was that a drunken idiot was about to attempt and fail at something they were in no way qualified for. Now people use it as a way to represent effortless success.
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Well things change and get warped over time. I always took as a way to try and one up someone maybe catastrophically failing at it, but still trying to anyway.
I don't have a good example of a saying that changed its meaning, but I love how a bomb and the bomb mean completely different things. If something is a bomb it's really bad, but if it's THE bomb, then it's incredibly good.