Psychobiography has the potential to reveal the complexity of individuals’ lives. Psychobiographies of well-known individuals have focused, with a few exceptions, primarily on analyses of the lives of well known White males, whose profiles and accomplishments have certainly been worthy of such attention. The availability of psychobiographies, however, of well known People of Color in history and contemporary contexts is quite limited. Additionally, psychobiographies of prominent women and especially Women of Color is also limited. This book will contribute to filling a void in the psychobiographical literature about prominent Black/African American individuals. This book is a multiple case psychobiography of the lives of four Black/African American performing artists Bert Williams (November 12, 1874 – March 4, 1922), Ethel Waters (October 31, 1896 – September 1, 1977), Dorothy Dandridge (November 9, 1922 – September 8, 1965), and Sammy Davis Jr. (December 8, 1925 – May 16, 1990). Bert Williams, Ethel Waters, Dorothy Dandridge, and Sammy Davis, Jr. were talented and successful Black/African American entertainers and artists. But, despite their talent and success, they faced unique barriers in the entertainment industry and in society in a variety of contexts, including but not limited to racism and sexism. Moreover, the eras that each of them came of age in were historical time periods that reflected particular societal mores and values related to race, culture, gender and other aspects of intersectionality. It is my belief that the attention and rewards they received as performing artists were not commensurate with their talent. This book will present a psychobiographical examination of each subject’s racial-cultural identity, personality, intersectionality, talent, and professional careers as well as their embeddedness in historical and contemporary cultural contexts.