Purpose — the study purpose is to explore the early history of head surgery in terms of artistic figures, based on authentic artistic artifacts of the past. Material and methods. We performed a detailed analysis of many paintings, engravings, and illustrations for medical publications of the Middle Ages and Renaissance, which were definitely related to the early development of head surgery. Results. The article summarizes a variety of illustrations that present the history of head surgery through images created by painters of the past, both recognized geniuses and those whose names have not been known to a non-specialist audience. Many artifacts are presented for the first time. Conclusion. We demonstrate that the art works reflect ideas of the past about life and death, causes of diseases, and their surgical treatment. At the same time, painters themselves, being an advanced part of the society, contributed to medicine, actively participating in the development of not only deontological norms but also people’s attitudes to their health and to those who chose medicine as their profession. Their works enable modern doctors to imagine the first neurosurgeons of the past.