Etymology

heads or tails

Today it means: The practice of flipping a coin in the air, to choose between two alternatives based on which side lands face up. Full definition →

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The story

Attested since at least 1833, on the second page of Galignani's Messenger: "amusing themselves by pitching quoits, spoiling halfpence at heads or tails with the gingerbread merchants, drinking beer, smoking, etc".

Etymology from Wiktionary, CC BY-SA 4.0.