Online Etymology Dictionary

cooler: 1610s, "a vessel in which something is set to cool," agent noun from cool (v.). Meaning "insulated box to keep things cool" is from 1958. Slang meaning "jail" is attested from 1884.
coolant: "radiator fluid," 1930, from cool + -ant.
coolth: 1547, from cool on the model of warmth. It persists, and was used by Pound, Tolkien, Kipling, etc., but it never has shaken its odor of facetiousness and become standard.
coolness: O.E. colnesse; see cool + -ness. Fig. sense is from 1650s, "calmness;" meaning "absence of warm affection" is from 1670s.
cool: O.E. col, from P.Gmc. *koluz, from PIE base *gel- "cold, to freeze." The v. form kele (from O.E. colian) was used by Shakespeare, but has been assimilated with the adj. into the modern word. Applied since 1728 to large sums of money to give emphasis to amount. Meaning "calmly audacious" is from 1825. Slang use for "fashionable" is 1933, originally Black English, said to have been popularized in jazz circles by tenor saxophonist Lester Young. Related: Cooling (mid-14c.); coolly (1570s).
refrigeration: 1471, "act of cooling or freezing," from L. refrigerationem "mitigation of heat," especially in sickness, noun of action from refrigerare, from re- "again" + frigerare "make cool," from frigus (gen. frigoris) "cold." Specifically of "freezing provisions as a means of preserving them" from 1881. Refrigerator "cabinet for keeping food cool" is first recorded 1824, originally in the brewery trade, in place of earlier refrigeratory (1605).
crunk: by 1999, style of popular music developed in U.S. South in 1990s; often said to be a contraction of crazy drunk. It was used early in a sense of "cool, good."
uncool: 1953, in hipster slang, from un- (1) "not" + slang sense of cool (adj.).
ill: c.1200, "morally evil" (other 13c. senses were "malevolent, hurtful, unfortunate, difficult"), from O.N. illr "ill, bad," of unknown origin. Not related to evil. Main modern sense of "sick, unhealthy, unwell" is first recorded c.1460, probably related to O.N. idiom "it is bad to me." Illness "disease, sickness" is from 1689. Slang sense of "very good, cool" is 1980s.
frigid: c.1420 (implied in frigidity), from L. frigidus "cold, chill, cool," from stem of frigere "be cold;" related to frigus "cold, coldness, frost." The meaning "wanting in sexual heat" is attested from 1660. Frigidaire as the proprietary name of a brand of refrigerators dates from 1926.
swale: "low, hollow place, often boggy," 1584, special use of Scottish swaill "low, hollow place," or dialectal East Anglian swale "shady place" (c.1440); both probably from O.N. svalr "cool," from P.Gmc. *swalaz.
cucumber: late 14c., from O.Fr. cocombre, from L. cucumis (acc. cucumerem), perhaps from a pre-Italic Mediterranean language. Replaced O.E. eorþæppla (pl.), lit. "earth-apples." Cowcumber was common form 17c.-18c., and that pronunciation lingered into 19c. Planted as a garden vegetable by 1609 by Jamestown colonists. Phrase cool as a cucumber (c.1732) embodies ancient folk knowledge confirmed by science in 1970: inside of a field cucumber on a warm day is 20 degrees cooler than the air temperature.
phlegmatic: "cool, calm, self-possessed," and in a more pejorative sense, "cold, dull, apathetic," 1570s, from lit. sense "abounding in phlegm (as a bodily humor)" (mid-14c.), from O.Fr. fleumatique, from L.L. phlegmaticus, from Gk. phlegmatikos "abounding in phlegm" (see phlegm).
"A verry flewmatike man is in the body lustles, heuy and slow." [John of Trevisa, transl. of Bartholomew de Glanville's "De proprietatibus rerum," 1398]
crazy: 1570s, "diseased, sickly, from craze; meaning "full of cracks or flaws" is from 1580s; that of "of unsound mind, or behaving as so" is from 1610s. Jazz slang sense "cool, exciting" attested by 1927. To drive (someone) crazy is attested by 1873. Phrase crazy like a fox recorded from 1935. Crazy Horse, Teton Lakhota (Siouan) war leader (d.1877) translates thašuka witko, lit. "his horse is crazy."
cyber: as a prefix, ultimately from cybernetics (q.v.). It enjoyed explosive use with the rise of the Internet early 1990s. One researcher (Nagel) counted 104 words formed from it by 1994. Cyberpunk (by 1986) and cyberspace were among the earliest.
Cyber is such a perfect prefix. Because nobody has any idea what it means, it can be grafted onto any old word to make it seem new, cool -- and therefore strange, spooky. ["New York" magazine, Dec. 23, 1996]
As a stand-alone, it is attested by 1998 as short for cybersex (which is attested by 1995).
fresco: 1598, in fresco, lit. "in fresh," with a sense of "painted on fresh mortar or plaster," from It. fresco "cool, fresh," from P.Gmc. *friskaz (see fresh).
adjective: early 15c., from O.Fr. adjectif (14c.), from L. adjectivum "that is added to (the noun)," neut. of adjectivus "added," from pp. of adicere "to throw or place (a thing) near," from ad- "to" + comb. form of jacere "to throw" (see jet (v.)). In 19c. Britain, often a euphemism for bloody.
"They ... slept until it was cool enough to go out with their 'Towny,' whose vocabulary contained less than six hundred words, and the Adjective." [Kipling, "Soldiers Three," 1888]
psyche: 1647, "animating spirit," from L. psyche, from Gk. psykhe "the soul, mind, spirit, breath, life, the invisible animating principle or entity which occupies and directs the physical body" (personified as Psykhe, the lover of Eros), akin to psykhein "to blow, cool," from PIE base *bhes- "to blow" (cf. Skt. bhas-). The word had extensive sense development in Platonic philosophy and Jewish-infl. theological writing of St. Paul. In Eng., psychological sense is from 1910.
sang-froid: "presence of mind, composure," 1712, from Fr. sang froid, lit. "cool blood," from sang "blood" (from L. sanguis) + froid "cold," from L. frigidus).
with: O.E. wið "against, opposite, toward," a shortened form related to wiðer, from P.Gmc. *withro- "against" (cf. O.S. withar "against," O.N. viðr "against, with, toward, at," M.Du., Du. weder, Du. weer "again," Goth. wiþra "against, opposite"), from PIE *wi-tero-, lit. "more apart," from base *wi- "separation" (cf. Skt. vi, Avestan vi- "asunder," Skt. vitaram "further, farther," O.C.S. vutoru "other, second"). In M.E., sense shifted to denote association, combination, and union, partly by influence of O.N. vidh, and also perhaps by L. cum "with" (as in pugnare cum "fight with"). In this sense, it replaced O.E. mid "with," which survives only as a prefix (e.g. midwife). Original sense of "against, in opposition" is retained in compounds such as withhold, withdraw, withstand. Often treated as a conjunction by ungrammatical writers and used where and would be correct. First record of with child "pregnant" is recorded from c.1200. With it "cool" is black slang, recorded by 1931.
truck (n.): "vehicle," 1611, "small wheel" (especially one on which the carriages of a ship's guns were mounted), probably from L. trochus "iron hoop," from Gk. trokhos "wheel," from trekhein "to run" (see truckle (n.)). Sense extended to "cart for carrying heavy loads" (1774), then to "motor vehicle for carrying heavy loads" (1930), a shortened form of motor truck (1916). The verb, meaning "to convey on a truck," is recorded from 1809, from the noun. Verbal meaning "dance, move in a cool way," first attested 1935, from popular dance of that name in U.S., supposedly introduced at Cotton Club, 1933. Trucker is first attested 1853, "worker who moves loads using a cart;" the motorized version is from 1955, a shortening of truck driver (pre-1931). Truck stop is attested from 1961.
fly (v.1): "to soar through air," O.E. fleogan (class II strong verb; past tense fleag, pp. flogen), from W.Gmc. *fleuganan (cf. O.H.G. fliogan, O.N. flügja, M.Du. vlieghen, Ger. fliegen), from PIE *pleu- "flowing, floating" (cf. Lith. plaukiu "to swim"). The O.E. plural in -n (cf. oxen) gradually normalized 13c.-15c. to -s. Notion of "flapping as a wing does" led to sense of "tent flap" (1810), which yielded (1844) "covering for buttons that close up a garment." Flying buttress is from 1669. Fly-fishing (from fly (n.)) is from 1653; while flying fish is from c.1511. Flying saucer first attested 1947, though the image of saucers for unidentified flying objects is from at least 1880s. Flying Dutchman ghost ship first recorded c.1830, in Jeffrey, Baron de Reigersfeld's "The Life of a Sea Officer." Slang phrase fly off the handle "lose one's cool" dates from 1825. On the fly is 1851. Flying colors (1706) is probably from the image of a naval vessel with the national flag bravely displayed.
shuck (v.): 1819, "to remove the shucks from," from noun (1674) meaning "husk, pod, shell," Amer.Eng., of unknown origin. Later used in ref. to the shells of oysters and clams (1872). Interjection shucks is 1847, from sense of "something valueless" (not worth shucks). Many extended senses are from the notion of "stripping" an ear of corn, or from the capers associated with husking frolics; e.g. "to strip (off) one's clothes" (1848) and "to deceive, swindle, cheat, fool" (1959); phrase shucking and jiving "fooling, deceiving" is suggested from 1966, in U.S. black English, but cf. shuck (v.) a slang term among "cool musicians" for "to improvise chords, esp. to a piece of music one does not know" (1957), and shuck (n.) "a theft or fraud," in use by 1950s among U.S. blacks.
"[B]lack senses probably fr[om] the fact that black slaves sang and shouted gleefully during corn-shucking season, and this behavior, along with lying and teasing, became a part of the protective and evasive behavior normally adopted towards white people in "traditional" race relations; the sense of "swindle" is perhaps related to the mid-1800s term to be shucked out, "be defeated, be denied victory," which suggests that the notion of stripping someone as an ear of corn is stripped may be basic in the semantics." ["Dictionary of American Slang"]