Word Origin & History
1855, theater slang for "a failure," by 1862 acquired the general sense of any dismal flop, on or off the stage. Via Fr. phrase fiare fiasco "turn out a failure," from It. far fiasco "suffer a complete breakdown in performance," lit. "make a bottle," from fiasco "bottle," from L.L. flasco, flasconem
). The reason for all this is utterly obscure today, but "the usual range of fanciful theories has been advanced" [Ayto]. Weekley finds it utterly mysterious and compares Fr. ramasser un pelle "to come a cropper (in bicycling), lit. to pick up a shovel." OED makes 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). That plausibly connects the word with the notion of "a costly mistake."