Anatomy has a long history that started with dissection of animals and then expanded and flourished thanks to dissections performed on human bodies. Artists had a crucial role in uncovering the secrets of human anatomy. While most studies have focused on the influence of famous Renaissance artists on human anatomy studies, the anatomical drawings by pre-Renaissance artists and local craftsmen have remained in their shadow. One of the most popular artistic genres in which complete or parts of human skeletons appear is the Dance of Death (Danse Macabre). This article is an anthropological study of two medieval Dance of Death frescoes that are unusual in being relatively early as well as accurately datable. A comparative morphological analysis of the two late 15th century works present in Istria has been conducted. The two works were painted by two local masters and show how the artists filled the gaps in their knowledge of human anatomy mostly with insights into animal bones and imagination. Their artworks, even though only 16 years apart, demonstrate substantial differences in the representation of the skeletons. The article argues that the history of medicine and of art could make good use of osteology and physical anthropology in attempts to define and understand how anatomical knowledge developed among pre-Renaissance and post-Renaissance artists and local people.