Fractures of the humerus have been diagnosed and classified since the time of the ancient Egyptians. This chapter introduces written records predating modern imaging. Swelling, inflammation, and crepitus were described in ancient Egypt, Greece, and Rome. The Hippocratic writings (c. 415 BCE) differentiated epiphyseal and diaphyseal fractures. Celsus (25 BCE–50 CE) described various morphological traits of fractures, including oblique, transverse, and comminuted fractures. The sources indicate that it was likely trauma rather than bone weakness that caused the injuries; descriptions of compound fractures support this assumption. Human dissections in Alexandria in the third century BCE and in medieval Italy in the twelfth century mainly served to confirm existing theoretical anatomical dogma. Naturalistic descriptions and illustrations, in a modern sense, emerged in the Renaissance with the pioneering contributions of Leonardo da Vinci (1452–1519) and Andreas Vesalius (1514–1564). The influence of Hippocrates and Galen (129–c. 215) lasted until the advent of pathological anatomy in the late eighteenth century, when autopsy findings were systematically compared with clinical findings. Written sources produced by a learned elite confirm that the described treatments were considered, although we have no reference to ancient practitioners treating shoulder fractures.