by c. 1200 as an emphatic form of Old English of (see of), employed in the adverbial use of that word. The prepositional meaning "away from" and the adjectival sense of "farther" were not firmly fixed in this variant until 17c., but once they were they left the original of with the transferred and weakened senses of the word. Meaning "not working" is from 1861.
Off the cuff "extemporaneously, without preparation" (1938) is from the notion of speaking from notes written in haste on one's shirt cuffs. In reference to clothing, off the rack (adj.) "not tailored, not made to individual requirements, ready-made" is by 1963, on the notion of buying it from the rack of a clothing store; off the record "not to be publicly disclosed" is from 1933; off the wall "crazy" is 1968, probably from the notion of a lunatic "bouncing off the walls" or else in reference to carom shots in squash, handball, etc.
slang, "perform male masturbation," by 1896, from jerk (v.) denoting rapid pulling motion + off (adv.). Compare come off "experience orgasm" (17c.). Farmer and Henley ("Slang and Its Analogues") also lists as synonyms jerk (one's) jelly and jerk (one's) juice. The noun jerk off or jerkoff as an emphatic form of jerk (n.2) is attested by 1968. As an adjective from 1957.