Dictionaries source the Spanish word guay (current meaning: cool/super/excellent/smashing) back to an (Arab) cry, ay. This never makes any kind of sense to me, since the latter is used to signal woe, grief and all manner of misery. Where did the current guay come from, and how (if at all) did this reversal of meaning occur?

Kalilah and Dimnah is a fabulous collection of Sanskrit animal-based moral tales, translated into Pahlavi around 550, to Arabic around 750, and then to Syriac, Greek, Hebrew, Latin and Old Spanish (Calila e Dimna (1251)) between the 11th and 13th centuries. One story (which may remind you of Isaac Bashevis Singer's The Slave) describes a lioness who, following the slaughter of her cubs by a hunter, regrets having spent her life consuming other animals' offspring. She stops eating meat and instead consumes all the vegetation, leaving her past prey to starve to death. Woe! woe! woe! Here's the relevant bit from the Spanish version:

Et quando la leona oyó lo que le dezía el anxahar, sopo que le dezía verdat, et aquello que le avía acaeçido non era salvo en pena de lo que ella feziera. Et dexó el venar et quitóse de comer carne, et comió fruta, et fizo vida de religioso. Et quando esto vio el anxahar et falló que la leona avía fecho gran astragamiento en la fruta del monte, fuese para ella et díxole: - Creo que los árvoles otro año [non] levarán fruta por tu cabsa, porque siendo comedera de carne comes fruta. Et si así ha de pasar, ¡guay de las frutas et de los árvoles et de las bestias salvajes que las comen, que priado pereçerán! (Source: RAE historical database. My italics.)

I think that there's a fairly good chance that this translation was by a Hispanic Jew, and from then until the present day there remains a strong association in Hispanic literature between guay and Jews. For example, in his Libro de los proverbios glosados (1570s) Sebastián de Horozco regrets that the ethnic cleansing conducted by the Catholic monarchs was not accompanied by a linguistic purge of Jewish expressions like guaya de ..., which he associates with sadness:

[Guaya de vos] es refrán judayco, de tiempo de judíos, entre los quales hazer la guaya era llorar y hazer duelo por algún mal que les venía. Y así en los mortuorios yban haziendo la guaya con los defunctos puestos con capirotes y otros fandularios judaycos. Y como en Toledo como tierra grassa y semejante a la de allá de Jerusalén quando algún trabajo les venía como pechos o serviçios de reyes o otros infortunios como les sería a ellos lo mandado y proveýdo por los Reyes Católicos quando fueron mandados ir destos reynos no siendo xpianos y quando vino el Sancto Ofiçio de la Inquisición y otras cosas contra su opinión de verdad es de creer que dirían, "Guaya de vos, Toledo," como quien le lloraba diziendo que se perdía. Por manera que el guay, o guaya o guayas era cosa de tristeza. Y así dezían guayar al llorar. Y así lloraba la hija del judío rico que se pensaba casar muy bien porque a la vejez le naçía otra hija a su padre que es lo que se dize por otro proverbio que dize, "Guayas, padre, y otra os naçe." Después de los judíos estas palabras, "Guaya de vos, Toledo," se suelen dezir para motejar a uno de judío mayormente si es de Toledo aunque de otras partes muchas se podría también dezir donde ovo tantos y más judíos. Mas como Toledo era la cabeça del reyno de Toledo y çibdad tan prinçipal como se le atribuýan y atribuyen otras muchas cosas buenas no es mucho ni es maravilla que se le atribuya esta pestilençia judayca que no es poca mohína para los buenos y limpios. Y espántome yo como el refrán de Guadalajara no se atribuyó a Toledo que dize, "Vizcaýno de Guadalajara," por dezir "bay," dixo, "guay." De manera que en Guadalajara aunque vizcaýnos, también guayaban y en todo lugar de xpianos donde avía judíos. Así que también se podría dezir, "Guaya de vos, sevillano," y "Guaya de vos, cordobés, etc."

Iten quando el judío dezía, "Guay si la saco," y a él prenosticaba el grande lloro y tristeza que avía de aver si él desenvaynaba su espada. Y así todos los refranes que comiençan por esta palabra, "guay," o "guayas," que son otros muchos que aquí no se ponen por su prolixidad denotan manera de amenaza y tristeza que se ha de seguir como, "Guay del solo," que en latín se significa por, "ve," como, "vesori," etc. y en nuestro vulgar dezimos, "ay," como, "Ay del solo, ay de tal, ay de qual." Por manera que la palabra, "guay," o "guaya," de los judíos es lo mesmo que nosotros dezimos, "ay," sino que no lo lloramos ni guayamos como ellos. Y así qualquiera se debe escusar de usar de estas palabras judaycas, "guay" ni "guaya," ni "guayas," ni otras semejantes pudiendo usar de las nuestras. Y con tanto pongo fin a las guayas. (Source: RAE historical database.)

If there is historical continuity and a change of meaning took place, then here are a couple of suggestions as to what might have happened:

  • Ladino/Judeo-Spanish proverbs are permeated by a bitter-sweetness which, as in the tale of the lioness, allows expression of the notion that any action may lead to exactly the opposite of the intended result. Like the good-bad/wicked/evil ex-dichotomy in English, this led to a double meaning for guay. This occurred among Maghrebi Sephardim after 1492 and, although I don't have access to the requisite dictionaries, I believe that güé means good in modern-day Moroccan Ladino. The word was re-imported to Spain in the 90s by Moroccan immigrants from a location with a substantial Sephardic community. It now exists side-by-side with the original meaning, which, preserved in Spanish, is fading fast. This scenario seems vaguely improbable to me.
  • It stayed in Spain and a local Michael Jackson fan changed the meaning. If this had happened, one would have expected a flood of newspaper articles and a triumphant lecture tour by the alteration's author. Nope.

It's also possible that the modern it is simply a new word. Again, here are a couple of hypotheses:

  • The Spanish bueno went on travels and passed either through the güé mill or through another, returning to Spanish in the form guay. I don't find this convincing.
  • X Fages suggests that it comes from the phrase esto es guay del Paraguay, la crème de la crème. If this is the case, then it might have arrived with recent Latin American immigrants. I'd be prepared to believe this, but there's no further evidence.
  • It has something to do with gai in French or with Breton names like Le Guay and Le Juich. I don't somehow think so.

OK, I give up. Tell me, someone.

  • Arabic language (45) Arabic i/ˈærəbɪk/ is a name for what are traditionally considered the descendants of the Classical Arabic language of the 6th century. This includes both the literary language and varieties of Arabic spoken in a wide arc of territory, stretching across the Middle East, North Africa, and the Horn of Africa. Arabic belongs to the Afro-Asiatic family.
  • Spain (1551)
  • Translation (531)
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