Etymology
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stiff (adj.)

Old English stif "rigid, inflexible," from Proto-Germanic *stifaz "inflexible" (source also of Dutch stijf, Old High German stif, German steif "stiff;" Old Norse stifla "choke"), from PIE *stipos-, from root *steip- "press together, pack, cram" (source also of Sanskrit styayate "coagulates," stima "slow;" Greek stia, stion "small stone," steibo "press together;" Latin stipare "pack down, press," stipes "post, tree trunk;" Lithuanian stipti "to stiffen, grow rigid," stiprus "strong;" Old Church Slavonic stena "wall"). Of battles and competitions, from mid-13c.; of liquor, from 1813. To keep a stiff upper lip is attested from 1815. Related: Stiffly.

stiff (n.)

"corpse, dead body," 1859, slang, from stiff (adj.) which had been associated with notion of rigor mortis since c. 1200. Meaning "working man" first recorded 1930, from earlier genitive sense of "contemptible person," but sometimes merely "man, fellow" (1882). Slang meaning "something or someone bound to lose" is 1890 (originally of racehorses), from notion of "corpse."

stiff (v.)

late 14c., "to make stiff," from stiff (adj.). Meaning "fail to tip" is from 1939, originally among restaurant and hotel workers, probably from stiff (n.), perhaps in slang sense of "corpse" (because dead men pay no tips), or from the "contemptible person" sense. Extended by 1950 to "cheat."

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Definitions of stiff
1
stiff (adj.)
not moving or operating freely;
a stiff hinge
stiff (adj.)
powerful;
a stiff current
a stiff breeze
stiff (adj.)
rigidly formal;
the letter was stiff and formal
Synonyms: starchy / buckram
stiff (adj.)
marked by firm determination or resolution; not shakable;
Synonyms: firm / steadfast / steady / unbendable / unfaltering / unshakable / unwavering
stiff (adj.)
incapable of or resistant to bending;
stiff hair
a palace guardsman stiff as a poker
a stiff neck
Synonyms: rigid
stiff (adj.)
very drunk;
Synonyms: besotted / blind drunk / blotto / crocked / cockeyed / fuddled / loaded / pie-eyed / pissed / pixilated / plastered / slopped / sloshed / smashed / soaked / soused / sozzled / squiffy / tight / wet
stiff (adj.)
having a strong physiological or chemical effect;
a stiff drink
Synonyms: potent / strong
2
stiff (n.)
an ordinary man;
a lucky stiff
a working stiff
stiff (n.)
the dead body of a human being;
the murderer confessed that he threw the stiff in the river
Synonyms: cadaver / corpse / clay / remains
3
stiff (adv.)
extremely;
bored stiff
frightened stiff
stiff (adv.)
in a stiff manner;
Synonyms: stiffly
From wordnet.princeton.edu