Entries linking to dickhead
"fellow, lad, man," 1550s, rhyming nickname for Rick, short for Richard, one of the commonest English names, it has long been a synonym for "fellow," and so most of the slang senses are probably very old, but naturally hard to find in the surviving records. The meaning "penis" is attested from 1891 in Farmer's slang dictionary (possibly British army slang). Meaning "detective" is recorded from 1908, perhaps as a shortened variant of detective. As a verb, "to bungle; to waste time," also "to cheat, treat badly," by 1969, American English (often with off or around).
The story of Dick Whittington's cat is an old one, told under other names throughout Europe, of a poor boy who sends a cat he had bought for a penny as his stake in a trading voyage; the captain sells it on his behalf for a fortune to a foreign king whose palace is overrun by rats. The hero devotes part of his windfall to charity, which may be why the legend in England has been attached since 16c. to Sir Richard Whittington (d. 1423), three times Lord Mayor of London, who died childless and devoted large sums in his will to churches, almshouses, and St. Bartholomew's Hospital.
Old English heafod "top of the body," also "upper end of a slope," also "chief person, leader, ruler; capital city," from Proto-Germanic *haubid (source also of Old Saxon hobid, Old Norse hofuð, Old Frisian haved, Middle Dutch hovet, Dutch hoofd, Old High German houbit, German Haupt, Gothic haubiþ "head"), from PIE root *kaput- "head."
Modern spelling is early 15c., representing what was then a long vowel (as in heat) and remained after pronunciation shifted. Of rounded tops of plants from late 14c. Meaning "origin of a river" is mid-14c. Meaning "obverse of a coin" (the side with the portrait) is from 1680s; meaning "foam on a mug of beer" is first attested 1540s; meaning "toilet" is from 1748, based on location of crew toilet in the bow (or head) of a ship.
Synechdochic use for "person" (as in head count) is first attested late 13c.; of cattle, etc., in this sense from 1510s. As a height measure of persons, from c. 1300. Meaning "drug addict" (usually in a compound with the preferred drug as the first element) is from 1911.
To be over (one's) head "beyond one's comprehension" is by 1620s. To give head "perform fellatio" is from 1950s. Phrase heads will roll "people will be punished" (1930) translates Adolf Hitler. Head case "eccentric or insane person" is from 1966. Head game "mental manipulation" attested by 1972.