Case study research allows for an in depth study of an individual and yields relevant insight and results while examining an individual in their entirety. This approach allows the researcher to capture the uniqueness of a subject and thus provide an interesting understanding of that individual. The study is a case study of Kurt Donald Cobain. Cobain (1967-1994) was an American musician who served as songwriter, lead singer and guitarist for the band, Nirvana. He struggled with drug addiction during the last years of his life, and died on 8 April 1994 from a self-inflicted gunshot wound to his head (Sandford, 1995). The study is a single case research design, utilizing both qualitative and quantitative data. It aimed to explore and describe Kurt Cobain’s personality according to the Five Factor Model of Personality. He was chosen as the research subject by means of purposive sampling on the basis of the researcher’s interest and on his uniqueness and inspirational influences on the general public. Collected data was analyzed in accordance with Huberman and Miles’s (1994) general approach which consists of data reduction, data display and conclusion drawing and verification. Descriptive tables from the NEO-PI-R personality measure were further interpreted to provide quantitative information regarding the personality traits of the subject. The findings of this study suggest that Kurt Cobain portrayed a complex personality profile as an individual, and it appears that he experienced much distress and emotional instability within his life. However, he was able to provide the youth a means of expressing themselves through his music.