Different religions and philosophies have sought to address the mysteries of death by envisioning an eternal afterlife. Three classic works reflecting human desire for immortality are described and analyzed: The Mesopotamian Epic of Gilgamesh, Oscar Wilde’s book The Picture of Dorian Gray, complemented with the film The Substance, and Simone de Beauvoir’s book All Men Are Mortal, complemented with the film The Age of Adaline. A comparison of these works raises several pressing questions: Given the finiteness of life, can the positions of “I as alive” and “I as dead” be reconciled more closely than what our death-averse culture has taught us? Can they, as integral parts of our lives, become companions that coexist, tolerate one another, and even thrive together?