c. 1600, "to flap," probably a variant of flap with a duller, heavier sound. Sense of "fall or drop heavily" is 1836; that of "collapse, fail" is 1919; though the figurative noun sense of "a failure" is recorded from 1893. Related: Flopped; flopping.
1823, "act of flopping; any action that produces the sound 'flop;' the sound itself," from flop (v.). Figurative sense of "a failure; that which is a failure" is by 1893, from the notion of a sudden break-down or collapse. Extended form flopperoo is attested by 1936. The Fosbury flop high-jumping technique (1968) is so called in reference to U.S. athlete Dick Fosbury (b. 1947), who used it to win the 1968 Olympic gold medal.