We see faces every day, and all of them leave us with different impressions. Our brains also respond emotionally to new and familiar faces we find in non-animated objects, paintings, and sculptures. To retain such memory of a face or express our feelings, we create portraits. Portraits have fascinated us for millennia. This paper reviews the interrelationships between painting, photography, facial recognition, and artificial intelligence technologies in portraiture aesthetics. The importance of portraits as a subject in artistic creation, studies, and research has led to various advancements in technological innovations. The inevitable role that portraits play in different mediums of art, history of art, communication, and security marks the intersection between humanity and identity, art and technology, as well as its undeniable position within the genre of art. Today the rapid development of digital tools, mobile software, and artificial intelligence allows not only the artist and designer to create portraitures but is also widely used by the public in all walks of life to create portraitures instantly. Driven by the marriage and momentum of art and technology in the field of new media art, will artificial intelligence and modern facial recognition technology take over the role of artists? Keywords: portrait, painting, photography, facial recognition technology, artificial intelligence