Upon review of the three pairs of paintings and statues (Frida Kahlo’s self-portrait) and Fayum woman, Enrique Chagoya’s image with Tony Ousler’s and the Olmec Colossal Head with the sculpture of Constantine the Great) (Author’s Family Name), one found the paired image of Frida Kahlo’s self-portrait and that of the Fayum woman as the most expressive. The rendition and depiction of these facial expressions of women through painting captured the most vivid expressions due to the clarity within which these images were created using the artists’ style, colors, and the manner by which some facets of the women’s emotions and feelings have been effectively captured through the paintings. Likewise, the image of the Young Woman with a Gold Pectoral showcased the face of an expressive female with eyes wide and lips that were a bit curled to relay a message of sophistication and proprietress within her time setting and realm. These images somehow effectively captured and relayed the intense emotions and sentiments felt by the painters or artists during the time these paintings were created. The other pairs were less expressive in terms of insufficient display of full meaning conveyed by the facial expressions; particularly the statues which were exhibited and interpreted as cold and formal structures of these identified personalities’ faces, devoid of facial expressions or any meaning that could be conveyed.This paper is a Comparative Facial Expressions of Three Pairs of Paintings and Statues.