This research is an attempt to understand and measure mythological roles in attributional processes. Drawing upon Carl Jung’s work on the archetype we, first, argue how role archetypes from fantasy dramas and worldwide fairy tales populate organizational life, and further, contend that they have extensive influence on how group members sort their judgments of each other. In the second part of the article, our understanding of role archetypes is aided by quantitative measurements: participants in 31 consecutive leadership development classes are asked which fellow classmates they spontaneously associate with each of seven good and seven bad fairy tale roles (deep roles), if any. Our main question is to evaluate the magnitude of agreement on the assignment of roles. Results give strong support to the assumption that group members quite easily categorize fellow members into stereotypes identified by fairy tale roles. Given the evidence in the present analysis, we posit that the role imagoes most frequently assigned (The Big Five of Fairy Tales) are isomorphic with core family roles, and further, that broad personality traits have their roots in archetypal imaginations. To more effectively secure that mythological mechanisms will not triumph over more rational, complex and balanced ways of judgments, we suggest that organizational research should acknowledge the subtle and hidden world of deep role archetypes.