An eCard:

Well, smartass isn’t directly a compound of the adjective smart ‘impertinent’ and the noun ass; instead, -ass serves here as an expressive extension of smart (as in sweet-ass ‘really sweet, big-ass ‘really big’, dumb-ass ‘really dumb’, etc.) — note He’s always asking smart-ass / dumb-ass questions — and the extended adjective was then nouned, giving an alternative to smart aleck, smartypants, and in fact the noun smarty.

The sense of smart here is glossed by NOAD2 as follows:

showing impertinence by making clever or sarcastic remarks: don’t get smart or I’ll whack you one.

And here’s Neal Whitman on obscentity-based intensifiers, taking off from sweet-ass car in an xkcd cartoon:

it looks like two of the obscenity-based intensifiers, fucking and as shit, can go with either predicative or attributive adjectives, while ass is limited to attributives. This peculiarity of ass may be a relic of its origin. Patricia O’Conner writes on her Grammarphobia blog that the original ass-suffixed adjective was big, and at first it was written big-assed, and referred to people that had big asses.

Then -assed was shortened to –ass, and -ass was reanalyzed as an intensifier and extended to use with other adjectives.


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