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Head or tail sound fine to my ESL ears. What's the reasoning behind the plural usage? I looked it up on etymonline but didn't find anything interesting.

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I have no proof of this, but I'm wondering if this originated as a possessive "head's side". (I'm pretty sure tail has always been used simply because it's the most obvious antonym for head.) –  Marthaª Jan 11 '12 at 1:13
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up vote 6 down vote accepted

The Oxford English Dictionary has one citation from 1801 which puts it in the singular, but the earliest citation, from 1684, has ‘heads or tails’. I think we must regard heads and tails,when found in this context, as examples of ‘pluralia tantum’, the term used to describe nouns that end in -s, but whose meaning is ‘collective or composite’. Other examples are dregs, thanks and remains.

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Surprisingly, no one has mentioned about the metaphor here. (cf.Wikipedia, I suspect that it is properly called a metonymy.)

In expressions like heads and tails, we really are not referring to the literal head or tail on a coin. The symbolism is merely a convenient way of referring to the obverse and reverse sides of the coin.

We generally use the plural when a metaphor or a symbolism is used this way to refer to a certain class of associated things . So, this is not unique to heads and tails alone.

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I'd be interested in other examples of plurals used for metonymy (where the plural is otherwise nonsensical). –  Marthaª Jan 11 '12 at 1:09
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Heads (plural) seems to come from the variety of kings and queens heads on coins.

Pluralising tails seems to purely be for consistency.

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Since the introduction of the pound coin in the UK, I think we've only had two "heads" (both QE2, obviously), but at least a dozen "tails". I don't know if that was the general pattern way back when the expression started. –  FumbleFingers Jan 2 '12 at 17:45
    
@Fumble: The current UK standard pound coin has one head on the obverse, but seven heads and seven tails on the reverse –  Henry Jan 2 '12 at 19:25
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