In Reply to: To stiff someone posted by John on July 14, 2008 at 17:23:
: 'To stiff someone', as in to not pay his bill, I believe came from the funeral industry. It may have derived from an executor's refusal to pay a dry cleaning bill for a burial suit (a suit previously left at the cleaner's by the deceased?), whether tendered by the undertaker or by the dry cleaner, I don't remember... obviously, my memory is unclear on the specifics.
www.etymonline.com says of stiff:
"fail to tip," 1939, originally among restaurant and hotel workers, probably from stiff (n.) in slang sense of "corpse" (corpses don't tip well, either). Extended by 1950 to "cheat."
The idea that the undertaker would have the job of picking up the dry cleaning or that the mourner would quibble over a few dollars on a very large bill both seem unlikely.