This study sheds light on the formative and expressive aspects of depicting the human face throughout the ages. It demonstrates the influence of various era characteristics, including cultural, social, ideological, and scientific features, on depicting the human face's formative and expressive aspects. Moreover, it demonstrates how depicting the human face expresses its era, the artist's artistic personality, and his or her formative style. The study presented models representing paintings depicting the human face across successive artistic stages, which the researcher divided into four basic stages based on the creative characteristics of each stage: First, the primitive arts stage; second, the arts of civilisations stage; third, the modern art stage; and finally, the postmodern arts stage (contemporary arts). The study discussed models depicting the human face in these successive artistic stages. The study concluded that the subject of depicting the human face reflects the characteristics of the era in which it was created, with all its cultural, social, ideological, and scientific aspects. Besides, it is concluded that portrait painting is a fundamental artistic subject addressed through the ages. The study also confirmed that portraiture can be considered a document reflecting the characteristics of an era, its arts, culture, and techniques.