Etymology
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smart (v.)
Old English smeortan "be painful," from Proto-Germanic *smarta- (source also of Middle Dutch smerten, Dutch smarten, Old High German smerzan, German schmerzen "to pain," originally "to bite"), from PIE *smerd- "pain," which is perhaps an extension of the root *mer- "to rub away; to harm." Related: Smarted; smarting.
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smart (adj.)
late Old English smeart "painful, severe, stinging; causing a sharp pain," related to smeortan (see smart (v.)). Meaning "executed with force and vigor" is from c. 1300. Meaning "quick, active, clever" is attested from c. 1300, from the notion of "cutting" wit, words, etc., or else "keen in bargaining." Meaning "trim in attire" first attested 1718, "ascending from the kitchen to the drawing-room c. 1880" [Weekley]. For sense evolution, compare sharp (adj.).

In reference to devices, the sense of "behaving as though guided by intelligence" (as in smart bomb) first attested 1972. Smarts "good sense, intelligence," is first recorded 1968 (Middle English had ingeny "intellectual capacity, cleverness" (early 15c.)). Smart cookie is from 1948.
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smart (n.)
"sharp pain," c. 1200, from smart (adj.). Cognate with Middle Dutch smerte, Dutch smart, Old High German smerzo, German Schmerz "pain."
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smart money (n.)
"money bet by those in the know," 1926, from smart (adj.). The same phrase earlier meant "money paid to sailors, soldiers, workers, etc., who have been disabled while on the job" (1690s), from a noun derivative of smart (v.). Also "money paid to obtain the discharge of a recruit" (1760), hence "money paid to escape some unpleasant situation" (1818). Sometimes in legal use, "damages in excess of injury done."
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smart-ass 
also smartass, 1960 (adj.), 1962 (n.), from smart (adj.) + ass (n.2).
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smart aleck (n.)
1865, of unknown origin, perhaps in reference to Aleck Hoag, notorious pimp, thief, and confidence man in New York City in early 1840s [Barnhart]. See smart (adj.). Related: Smart-alecky.
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smarty (n.)
"would-be witty or clever person," 1854, from smart (n.) + -y (3). Extended form smarty-pants first attested 1939.
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smartness (n.)
c. 1300, "severity," from smart (adj.) + -ness. From 1752 as "trimness," 1800 as "cleverness."
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smartly (adv.)

early 13c., "vigorously," from smart (adj.) + -ly (2). Meaning "handsomely" is by 1748.

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