How did this use of the word kicker enter the English language, and is its use localized to any one region?
An unexpected situation or detail.
Examples:
John wants to climb the wall, but the kicker is that it is thirty feet tall.
Here's the kicker: my sweater, which cost hundreds of both dollars and hours, doesn't fit. The sleeves are a good six inches too short... Here's the kicker to the kicker: I don't care.
Answer
Kicker, as in "here's the kicker", likely comes from poker. The kicker is a card used to break ties in hands of the same rank. The origin of that card's name (and how it is related to other kick idioms) is more difficult to determine.
Ngrams, however dubious, seems to suggest that the idiom is relatively recent:

Poker has a rich history of slang, and several other objective cards have specific names such as river, turn, et al. Other poker related idioms include up the ante, play your cards right, raise the stakes, wild card, and others.
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