"cheap hotel," hobo slang, 1904, probably related to slang flop (v.) "lie down for sleep" (1907); see flop (v.) + house (n.). The explanation below is not found in other early references.
In one of [Cincinnati's] slum districts stands the Silver Moon, a "flop house" (i.e., a house where the occupants are "flopped" out of their hanging bunks by letting down the ropes) .... [McClure's magazine, November 1904]
"botch, bungle," 1924, American English, of uncertain origin, perhaps suggested by fluff, flop, etc. Related: Flubbed; flubbing. As a noun, by 1952.
mid-15c., philippen "to flip something with the fingers, snap the fingers," possibly of imitative origin. As a noun, from 1520s, fyllippe.
limb used to swim with, 1822, agent noun from flip (v.). Sense of "rubber fin for underwater swimming" is from 1945. Slang meaning "the hand" dates from 1836. Related: Flippers.
"struggle awkwardly and impotently," especially when hampered somehow, 1590s, of uncertain origin, perhaps from an alteration of founder (n.), influenced by Dutch flodderen "to flop about," or native verbs in fl- expressing clumsy motion. Figurative use is from 1680s. Related: Floundered; floundering. As a noun, "act of struggling," by 1867.
1540s, "to dash, plunge, flop," perhaps from Scandinavian (compare dialectal Swedish flunsa "to plunge," Norwegian flunsa "to hurry, work hurriedly," but first record of these is 200 years later than the English word), said to be of imitative origin. Spelling likely influenced by bounce. Notions of "anger, impatience" began to adhere to the word 18c. Related: Flounced; flouncing. As a noun from 1580s in reference to a sudden fling or turn of the body; by mid-18c. especially as expressing impatience or disdain.
1826, "supply with a wig," from wig (n.). The earlier verb was bewig (see bewigged). The meaning "to behave hysterically" (usually with out) is attested from 1955, perhaps from notion in flip one's wig. Compare dash my wig!, a former mild imprecation (1797), also wigs on the green (1856), Irish colloquial for "a fight or rumble" (because wigs are likely to get detached from owners in such an event). The verb also had a colloquial sense of "scold severely," attested by 1829, perhaps related to these. Related: Wigged; wigging.
1948, shortening of bebop or rebop. The musical movement had its own lingo, which was in vogue in U.S. early 1950s. "Life" magazine [Sept. 29, 1952] listed examples of bop talk: crazy "new, wonderful, wildly exciting;" gone (adj.) "the tops—superlative of crazy;" cool (adj.) "tasty, pretty;" goof "to blow a wrong note or make a mistake;" hipster "modern version of hepcat;" dig "to understand, appreciate the subtleties of;" stoned "drunk, captivated, ecstatic, sent out of this world;" flip (v.) "to react enthusiastically."
1855, theater slang for "a failure in performance;" by 1862 it had acquired the general sense of "any ignominious failure or dismal flop," on or off the stage. It comes via the French phrase faire fiasco "turn out a failure" (19c.), from Italian far fiasco "suffer a complete breakdown in performance," literally "make a bottle," from fiasco "bottle," from Late Latin flasco "bottle" (see flask).
The literal sense of the image (if it is one) is obscure today, but "the usual range of fanciful theories has been advanced" [Ayto]. Century Dictionary says "perhaps in allusion to the bursting of a bottle," Weekley pronounces it impenetrable and compares French ramasser un pelle "to come a cropper (in bicycling), literally to pick up a shovel." OED keeps its distance and lets nameless "Italian etymologists" make nebulous reference to "alleged incidents in Italian theatrical history." Klein suggests Venetian glass-crafters tossing aside imperfect pieces to be made later into common flasks. But according to an Italian dictionary, fare il fiasco used to mean "to play a game so that the one that loses will pay the fiasco," in other words, he will buy the next bottle (of wine). If the dates are not objectionable, that plausibly connects the literal sense of the word with the notion of "a costly mistake."