The purpose of this study was to apply psychobiography to the lives of Hillary Clinton and Condoleezza Rice. Psychobiography can be applied as a method of teaching personality theory and it can also be used as a research method. Most political personas are crafted through 20 second sound bites from the radio, Internet, and television. However, a much more comprehensive and enriched perspective can be developed when exploring developmental backgrounds of influential figures. In particular, studying psychological features sheds light on the person's personality, motivations, and relationship styles. The Big 5 Personality Model was applied along with the Myers-Briggs Profile. The applications of these models highlight important personality characteristics that contribute to their achievements and failings. For example, both Clinton and Rice were rated high in the area of conscientiousness but differed in agreeableness and emotional expression. The authors recommend using psychobiography as an innovative method of teaching personality theory and as a method of understanding the lives of influential people.