Etymology

cold enough to freeze the balls off a brass monkey

Today it means: Extremely cold. Full definition →

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The story

Unknown. There is a discredited theory that it refers to a brass container for cannon balls on a British man-of-war, and a somewhat more plausible theory that "brass monkey" used to refer to a cannon on a man-of-war.

Etymology from Wiktionary, CC BY-SA 4.0.