"The word has in mod.Eng. a much stronger sense than it had at an earlier period; it has now an implication of insulting contempt which does not in the same degree belong to any of its synonyms, or to the derivative foolish." [OED]Meaning "jester, court clown" first attested 1370, though it is not always possible to tell whether the reference is to a professional entertainer or an amusing lunatic on the payroll. As the name of a kind of custard dish, it is attested from 1598 (the food was also called trifle, which may be the source of the name). The verb meaning "to make a fool of" is recorded from 1596. Feast of Fools (c.1320), from M.L. festum stultorum) refers to the burlesque festival celebrated in some churches on New Year's Day in medieval times. Fool's gold "iron pyrite" is from 1882. Fool's paradise "state of illusory happiness" is from 1462. Fool around is 1875 in the sense of "pass time idly," 1970s in sense of "have sexual adventures." Foolosopher, a most useful insult, turns up in a 1549 translation of Erasmus.
A fool there was and he made his prayer
(Even as you and I!)
To a rag and a bone and a hank of hair
(We called her the woman who did not care)
But the fool, he called her his lady fair
(Even as you and I.)
[Kipling, "The Vampire"]
FOOL: ... The reason why the
seven stars are no more than seven is a pretty reason.
KING LEAR: Because they are not eight?
FOOL: Yes, indeed: thou wouldst make a good fool.
["King Lear," Act I, Scene V]
"This is not an objective, anatomical term, neither does it imply coitus. It connects with that extension of meaning of the unprintable, a fool, or a person whom one does not like." ["Dictionary of Rhyming Slang," 1960]
"[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"]
"Saint - A dead sinner revised and edited. The Duchess of Orleans relates that the irreverent old calumniator, Marshal Villeroi, who in his youth had known St. Francis de Sales, said, on hearing him called saint: 'I am delighted to hear that Monsieur de Sales is a saint. He was fond of saying indelicate things, and used to cheat at cards. In other respects he was a perfect gentleman, though a fool.' " [Ambrose Bierce, "Devil's Dictionary," 1911]Meaning "person of extraordinary holiness" is recorded from 1563. The verb meaning "to enroll (someone) among the saints" is attested from late 14c. Applied widely to living things, diseases, objects and phenomena, e.g. Saint Bernard, the breed of mastiff dogs (1839), so called because they were used by the monks of the hospice of the pass of St. Bernard (between Italy and Switzerland) to rescue snowbound travelers; St. Elmo's Fire "corposant" (1560s) is from It. fuoco di Sant'Elmo, named for the patron saint of Mediterranean sailors, a corruption of the name of St. Erasmus, an Italian bishop martyred in 303.
" 'You're a fool nigger, and the worst day's work Pa ever did was to buy you,' said Scarlett slowly. ... There, she thought, I've said 'nigger' and Mother wouldn't like that at all." [Margaret Mitchell, "Gone With the Wind," 1936]Used in combinations (e.g. nigger-brown, nigger-head, nigger-toe) since 1840s for various dark brown or black hues or objects; euphemistic substitutions (e.g. Zulu) began to appear in these senses c.1917.