Psychobiography can be viewed as the re-writing of an individual’s life story previously undetected. In general it consists of a combination of two central elements: biography and psychological theory that aim to explain the particular individual’s psychological development. This particular study serves to explore the extraordinary life of renowned singer, songwriter, artist and activist, John Winston Lennon (1940-1980). The basis for this investigation will take the form of notable biographical accounts of the subject’s life, together with Austrian psychiatrist Alfred Adler’s (1938) theory of Individual Psychology, which recognizes the importance of human society for the development of individual character and the orientation of every single action and emotion in the life of a human being. Adler’s theory further explores that the main motives of human thought and behaviour are an individual’s striving for superiority and power, partly in compensation for his feeling of inferiority. The psychobiographical data collection and analysis for this research thesis will be guided by Yin’s (1994) theory of ‘analytic generalisation’, which uses a theoretical framework in selecting relevant data which develops a matrix as a descriptive framework for organizing and integrating that data, and Alexander’s (1988) analytical model which focuses on lifting out themes through principal identifiers of salience was used and applied. John Winston Lennon expressed his personal experiences and ideals through his songs and became the spokesman for his generation on modern day issues such as feminism and world peace. It is however, unfortunate that Lennon throughout his life remained a boy who felt rejected and unloved by his parents and strove to be superior in all aspects of his rich life in an attempt to acquire the love and acceptance that was not bestowed on him as a child.