The purpose of this research is to investigate, re-evaluate and synthesize earliest images depicting the Gorgoneion (gorgon’s head) and Gorgon (whole-body). These figures refer to prehistory covering a wide chronological frame in the Aegean World. Ten artefacts in total comprising of pottery, masks, seals are examined simultaneously for the first time. A detailed, critical evaluation of their dating, and the trade connections between mainland Greece and the Aegean are discussed. The issue is about making a symbol of the deceased introduced much earlier than the Archaic and later antiquity, showing the evolution of this form and the associated mythology has deep roots in the remote past. The forms of the Gorgon of the Archaic period depict a monster demon-like bellows, with feathers, snakes or spiral tentacles in the head, tongue protruding from the mouth and tusks. Snakes are the predominant element of this gorgon, which composes the gargoyle’s hairstyle. This figure is identified and appropriately assessed from a dozen of images in pottery and semiprecious stones, in the wider prehistoric Aegean, making the related myths on Gorgon-Medusa interwoven with myths that have had a wide reflection throughout the later ancient times.