I remember reading that this sort of motif was popular in the 14th to 17th centuries because of the black plague. Death had been so widespread, swift and indiscriminate (affecting rich and poor and people of all backgrounds alike) that everyone was coping with having its shadow constantly looming over them. That notion was reflected in artwork where skeletons were often depicted cavorting with the living or looming behind portraits of young, healthy-looking people.
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