Etymology
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lot (n.)

Old English hlot "object used to determine someone's share" (anything from dice to straw, but often a chip of wood with a name inscribed on it), also "what falls to a person by lot," from Proto-Germanic *khlutom (source also of Old Norse hlutr "lot, share," Old Frisian hlot "lot," Old Saxon hlot, Middle Dutch, Dutch lot, Old High German hluz "share of land," German Los), from a strong verb (the source of Old English hleotan "to cast lots, obtain by lot; to foretell"). The whole group is of unknown origin.

The object was placed with others in a receptacle (such as a hat or helmet), which was shaken, the winner being the one whose name or mark was on the lot that fell out first. Hence the expression cast lots; to cast (one's) lot with another (1530s, originally biblical) is to agree to share winnings. In some cases the lots were drawn by hand, hence to draw lots. The word was adopted from Germanic into the Romanic languages (Spanish lote, and compare lottery, lotto).

Meaning "choice resulting from the casting of lots" first attested c. 1200. Meaning "share or portion of life" in any way, "that which is given by fate, God or destiny" is from c. 1300. Meaning "number of persons or things of the same kind" is from 1570s (compare Latin mala merx, of persons, literally "a bad lot"). Sense of "plot of land" is first recorded 1630s, American English (distribution of the most desirable properties in new settlements often was determined by casting lots), then especially "parcel of land set aside for a specified purpose" (the Hollywood sense is from 1928). The common U.S. city lot was a rectangle 25 feet wide (along the street) by 100 deep; it was so universal as to be sometimes a unit of measure.

Meaning "group, collection" is 1725, from the notion of auction lots. Lots in the generalized sense of "great many" is attested by 1812; lotsa, colloquial for "lots of," is from 1927; lotta for "lot of" is by 1906.

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chestnut (n.)

type of tall tree native to western Asia, southern Europe, and eastern U.S., also the large "nut" that it produces, 1560s, from chesten nut (1510s), with superfluous nut (n.) + Middle English chasteine, from Old French chastain (12c., Modern French châtaigne), from Latin castanea "chestnut, chestnut tree," from Greek kastaneia, which the Greeks explained as either "nut from Castanea" in Pontus, or "nut from Castana" in Thessaly, but probably both places are named for the trees, not the other way around, and the word is borrowed from a language of Asia Minor (compare Armenian kask "chestnut," kaskeni "chestnut tree"). In reference to the dark reddish-brown color, 1650s. Applied to the horse-chestnut by 1832.

Slang sense of "venerable joke or story" is from 1885, explained by U.S. actor Joseph Jefferson ("Lippincott's Monthly Magazine," January 1888) as probably abstracted from the 1816 melodrama "The Broken Sword" by William Dimond where an oft-repeated story involving a chestnut tree figures in an exchange between the characters "Captain Zavior" and "Pablo":

Zav. Let me see—aye! it is exactly six years since, that peace being restored to Spain, and my ship paid off, my kind brother offer'd me a snug hammock in the dwelling of my forefathers;—I mounted a mule at Barcelona, and trotted away for my native mountains. At the dawn of the fourth day's journey, I entered the wood of Collares, when, suddenly from the thick boughs of a cork-tree—
Pab. [Jumping up.] A chesnut, Captain, a chesnut!
Zav. Bah! you booby, I say, a cork.
Pab. And I swear, a chesnut—Captain! this is the twenty-seventh time I have heard you relate this story, and you invariably said, a chesnut, till now.
Zav. Did I? Well, a chesnut be it then. But, take your seat again.

Jefferson traced the connection through William Warren (1812-1888), "the veteran comedian of Boston" (and Jefferson's cousin) who often played Pablo in the melodrama.

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mad (adj.)

late 13c., "disordered in intellect, demented, crazy, insane," from Old English gemædde "out of one's mind" (usually implying also violent excitement), also "foolish, extremely stupid," earlier gemæded "rendered insane," past participle of a lost verb *gemædan "to make insane or foolish," from Proto-Germanic *gamaidjan, demonstrative form of *gamaidaz "changed (for the worse), abnormal" (source also of Old Saxon gimed "foolish," Old High German gimeit "foolish, vain, boastful," Gothic gamaiþs "crippled, wounded," Old Norse meiða "to hurt, maim").

This apparently is from the Germanic intensive prefix *ga- + PIE *moito-, past participle of root *mei- (1) "to change, go, move" (source also of Latin mutare "to change," migrare "to change one's place of residence"). In Middle English usurped the place of the more usual Old English word, wod (see wood (adj.)).

The meanings "beside oneself with excitement or enthusiasm, under the influence of uncontrollable emotion" and "enraged, furious, beside oneself with anger" are attested from early 14c., but the latter was deplored by Rev. John Witherspoon (1781) as an Americanism. It now competes in American English with angry for this sense. Of animals, "affected with rabies, furious from disease" from late 13c.

To do something like mad "recklessly, as if mad or crazy" is by 1650s. Phrase mad as a March hare is attested from 1520s, via notion of breeding season; mad as a hatter is from 1829 as "demented," 1837 as "enraged," according to a modern theory supposedly from erratic behavior caused by prolonged exposure to poison mercuric nitrate, used in making felt hats. For mad as a wet hen see hen.

Mad money, which a young woman carries for use in getting home when she and her date have a falling out, is attested by 1922; mad scientist, one so eccentric as to be dangerous or evil, is by 1891. Mad Libs, the word game (based on the idea in consequences, etc.), was first published in 1958

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fairy (n.)

c. 1300, fairie, "the country or home of supernatural or legendary creatures; fairyland," also "something incredible or fictitious," from Old French faerie "land of fairies, meeting of fairies; enchantment, magic, witchcraft, sorcery" (12c.), from fae "fay," from Latin fata "the Fates," plural of fatum "that which is ordained; destiny, fate," from PIE root *bha- (2) "to speak, tell, say." Also compare fate (n.), also fay.

In ordinary use an elf differs from a fairy only in generally seeming young, and being more often mischievous. [Century Dictionary]

But that was before Tolkien. As a type of supernatural being from late 14c. [contra Tolkien; for example "This maketh that ther been no fairyes" in "Wife of Bath's Tale"], perhaps via intermediate forms such as fairie knight "supernatural or legendary knight" (c. 1300), as in Spenser, where faeries are heroic and human-sized. As a name for the diminutive winged beings in children's stories from early 17c.

Yet I suspect that this flower-and-butterfly minuteness was also a product of "rationalization," which transformed the glamour of Elfland into mere finesse, and invisibility into a fragility that could hide in a cowslip or shrink behind a blade of grass. It seems to become fashionable soon after the great voyages had begun to make the world seem too narrow to hold both men and elves; when the magic land of Hy Breasail in the West had become the mere Brazils, the land of red-dye-wood. [J.R.R. Tolkien, "On Fairy-Stories," 1947]

Hence, figurative adjective use in reference to lightness, fineness, delicacy. Slang meaning "effeminate male homosexual" is recorded by 1895. Fairy ring, of certain fungi in grass fields (as we would explain it now), is from 1590s. Fairy godmother attested from 1820. Fossil Cretaceous sea urchins found on the English downlands were called fairy loaves, and a book from 1787 reports that "country people" in England called the stones of the old Roman roads fairy pavements.

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