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.
on prep., adv.
"in a position above and in contact with; in such a position as to be supported by;" also noting the goal to which some action is or has been directed; "about, concerning, regarding; in a position to cover;" as an adverb, "in or into a position in contact with and supported by the top or upper part of something; in or into place; in place for use or action; into movement or action; in operation," Old English on, unstressed variant of an "in, on, into," from Proto-Germanic *ana "on" (source also of Dutch aan, German an, Gothic ana "on, upon"), from PIE root *an- (1) "on" (source also of Avestan ana "on," Greek ana "on, upon," Latin an-, Old Church Slavonic na, Lithuanian nuo "down from").
Also used in Old English in many places where we now would use in. From 16c.-18c. (and still in northern England dialect) often reduced to o'. Phrase on to "aware" is from 1877.
side-on adv.
1909, "with one side facing," from side (n.) + on (adv.), perhaps based on earlier head-on. In reference to a vehicle collision, by 1828.