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I'd always associated "oy vey" with "oy vavoy" in my mind. But I've seen sefarim that use the term אוי ואבוי, and I don't even know how to spell "oy vey" - much less ever seen it authoritatively written. According to Wikipedia, this phrase has its origins in cultural Judaism (Yiddish) from the 18th century, but there seem to be theories that it is older. There does seem to be a history of similar terms being used, as @TheTargum pointed out - the Yalkut Shimoni mentions a "ווי ווי" that the people said during the bad times of Megillas Esther.

Is this term indeed derived from Tanach or other holy books? Or is it just a nonsensical "Yiddishism" that kind of made it through the generations from grandmothers to their kids?

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  • See Wikipedia above; it appears to be Germanic. But "Oy" and "Avoy" are Biblical; Mishlei 23:29 writes that the drunk suffers from both. לְמִי אוֹי לְמִי אֲבוֹי sefaria.org/…
    – Shalom
    Jan 11 at 16:30
  • see also Midrash Lekach Tov sefaria.org/…
    – The Targum
    Jan 11 at 17:16

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There is similar use to the term Oy Vey that is refrenced in the midrashim on Megillas Esther.

In describing the choice of using the first word of the megillah as ויהי, the Yalkut Shimoni as well as Midrash Lekach Tov say that it comes from the etymology of the distressing phrase the jewish people used to describe their situation "ווי ווי"

See also the ancient Midrash Tanchuma on Parshas Shmini where he explains a similar use of the phrase "vey" to express distress. Similar explanation given by Ruth Rabbah

Maybe most significantly, in Bereishis Rabbah it uses the term "Oy Vey" albeit in reverse order "וְאוֹמֵר וַוי אוֹי אוֹי שֶׁהִכְעַסְתִּי לְבוֹרְאִי"

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