Most likely first used in the early 1900s, either refers to a sarcastic remark about Toledo, Ohio or originated from a realistic remark of the Holy city of Toledo, Spain. It is now used as a phrase, by Americans, if something is unbelievable, disturbing, or blows their mind. See blow your mind
Woman- Did you read in the newspaper that a grandpa got run over by his own car by a homeless bum he paid to fix it, and then the bum took off with it?
Man- Holy Toledo?! That's like "Grandma Got Ran Over By a Reindeer" only a hundred times worse!
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