Psychoanalysis is one of the most controversial and critical approaches to literature. Psychological evaluation of literary texts developed simply as modern psychology commenced its development at some point of the early 20th century by the Austrian Neurologist Sigmund (Freud, 2015). Psychoanalysis is embedded in the idea that humans have unconscious yearnings and assumes that characters are the outcome of different forces correlating their unconscious drives and their suppressed feelings, apart from the manipulation of different social and cultural conditions. Samuel Beckett and Harold Pinter are of the most highly regarded and widely performed playwrights who have captured the anxiety and ambiguity of life in the second half of the 20th century. The Nobel laureates are two major proponents of the ‘Theater of Absurd’, an avant-garde theatre movement in the middle of the 20th century which underscored the absurdity and bewilderment of human existence in the post-World War II era. The destruction brought about by the war affected the personal, social and political life of millions of people all over Europe and created a sense of severe depression, self-fragmentation, and mental conflicts within human beings. This paper approaches (Beckett, 1958) and Pinter’s Pinter et al. (2006) from a psychological perspective as it provides a perception of human nature, its anxieties, cravings, conflicting impulses, and hidden motivation. The paper includes a brief reference to the 'Theater of Absurd' movement to which the plays belong, to set the basis for the review of the plays understudy; then it touches shortly upon the Freudian Psychoanalytic Theory. Afterwards, the study dwells on the evaluation of the plays through the lens of Freud’s Psychoanalytic Theory. Finally, the study reaches a conclusion that contributes to our perception of psychological theories and allows us to better understand our complex psyche and experiences of the world.