Drawing from the models of contemporary personality psychology, this qualitative study analyses the characters of Greek mythological heroes as depicted in Homer's Illiad. First, it summarizes the current personality research as well as what psychodiagnostic methods there are for measuring different personality variables. In the next part, the authors describe the procedure they used for the verification of historical and intercultural validity of the personality models outlined earlier. Here they also present the results of their analysis with the conclusion that ancient Greek accounts testify to the universality of human nature throughout ages and cultures. At this point, the study also shows the hypothesized personality profiles of two major heroes, Achilles and Agamemnon. The following part of the article is dedicated to yet another psychological discourse: specifically how and why their motives and behavioural tendencies might cause clashes in their interaction, and also what occupational options they would probably face nowadays. Interdisciplinary in its nature, the paper finishes with the implications of the results for philosophy.