While these days it's most often used to imply intelligence, in Old English, “smart” had to do with pain, both as a verb (smeortan) and as an adjective (smeart). It was still painful when Shakespeare wrote Antony and Cleopatra in the early 1600s. In the play, when bad news is brought to Cleopatra, she scolds the messenger:
Thou shalt be whipp'd with wire, and stew'd in brine,
Smarting in lingering pickle.
Essentially, she threatens to soak the poor man in salt water, like a pickle, after his whipping, so that the “smarting” will last longer.
To this day, something that smarts, hurts, but as early as the 1200s, an adverb form of “smart” meant “vigorously,” which could be applied to any activity. The vigor could even be mental, as in keen bargaining, a development that likely led to the primary modern definition: intelligent.
The Pain of Being Smart
By the end of the 13th century, the adjective had also come to mean clever, but with a cutting wit. The great 18th-century satirist Jonathan Swift described ridicule in Gulliver’s Travels (1726): “He seldom failed of a smart word or two upon my littleness.” Here, the word is used in that sense with the warning, “Don’t get smart with me.”
“Smart” wasn’t the first word to link intelligence with things that cut and hurt; the Old English word for “sharp” (scearp) described knives but also had a figurative meaning of clever and cruel. By 1850, “incisive” made a similar journey from “painful cutting” to “vigorous thought.”
We see this evolution in the phrase “smart money,” which, in the 1690s, meant “pain money”: payments to sailors and soldiers to compensate them for wounds and injuries. The current sense — related to the investments of people who are money-savvy (referred to as “the smart money”) — arose during the stock boom of the late 1920s, shortly before the crash.
That Smarts!
In the early 1700s, the phrase “smarten up” meant to wear better-quality clothing, not necessarily an improvement in style or fashion. It took about 200 years for both “sharp” and “smart” to mean “stylish.” At least by the mid-1900s, women had mostly stopped wearing painfully stiff, boned corsets as “sharp” fashion.
The first “smart aleck” may have been Aleck Hoag, a notorious New York con man known for outsmarting the police in the 1840s. The idiom “smart cookie” arrived in 1948, and “smarts” as a noun popped up two decades later. Years before the iPhone, “smart” came in handy to describe devices that behaved as if they could think — for example, the smart bomb (1972) and the smartphone (1978).
While “smart” came into being as a cutting pain, today it’s possible to be smart and kind at the same time. But the history of this word suggests a moral: The smarter we are, the more our words can smart. Wear those smart and stylish pants, but don’t be a smarty-pants.
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