In an Italian restaurant of a bygone era—red-checked tablecloths, amateurishly but lovingly painted mural of the Bay of Naples, “O Sole Mio” or “Funiculì Funiculà” on the sound system—you might order a vino rosso, perhaps a Chianti, to accompany your spaghetti and meatballs or pizza.  The wine would arrive in a special bottle, slightly bulbous and straw-encased: a fiasco, the Italian word for “flask.”  Or a decorative item on your table might be an empty fiasco transformed into a candle holder, with melted wax dripping colorfully down the neck:  

Source: www.pinterest.com

Buon appetito!

How do we get from the “bottle” sense of “fiasco” to its current sense, “catastrophe, balls-up, total flop,” which fiasco also has in modern Italian?  We go to Italian theatrical slang, where the phrase far fiasco means “to mess up a performance,” say by forgetting your lines or stumbling over the stage furniture.  According to a quotation cited in the OED, this meaning of “fiasco” came into English as early as 1855: “what the theatrical people call a fiasco” (note the italics: it was still a foreign word). 

So far, so good.  It makes sense that an actor’s failing might lead to a catastrophe for the whole play.  But what does a bottle or flask have to do with an actor’s failing?  The authoritative Dizionario Etimologico della Lingua Italiana, at first scrupulously skeptical (“No convincing explanation has been given”), then proceeds to give a historical explanation which even if incorrect is too charming not to record.  In the seventeenth century, so the story goes, the great Italian actor Domenico Biancolelli specialized in the role (or “mask”) of Arlecchino in the commedia dell’ arte, Arlecchino being a witty, resourceful servant who dressed, like the French Harlequin, in checkered motley:  

Biancolelli was famous for his croaking voice, and no doubt it was in just such a voice that, one evening, he improvised a monologue about the bottle or fiasco which he was carrying.  But the audience failed to laugh.  So the actor turned to the bottle and said “It’s your fault if I’m a jerk this evening” (I am translating somewhat loosely), then threw the bottle over his shoulder.  Afterwards, when actors experienced misfortunes onstage, people said “É il fiasco d’Arlecchino!,” “It’s Arlecchino’s bottle!,” a phrase destined to be shortened in time to the one word “fiasco.”