This dissertation significantly expands our knowledge of the biography and artistic contributions of Hughie Lee-Smith (1915–1999), an African American artist. I argue that between 1925 and 1968 Lee-Smith’s personal, educational, and professional experiences within the context of Jim Crow America and the Cold War era influenced the style and content of his figurative work and his opportunities for success. Throughout the dissertation, I examine his inspirations from art history and position his works alongside those of his contemporaries to show that his paintings are based on observations, artistic influences, and imagination. The dissertation’s four chapters are organized around Lee-Smith’s experiences of living during these decades in Cleveland, Detroit, and New York. Chapter one examines his early years (1925–1940) in Cleveland, Ohio, after he relocated from the South to join his mother. He learned to acquire the necessary skills in art, experienced enthusiastic civic and private philanthropic support, and developed a personal philosophy about the ability of art to build a better society. Chapter two moves to Detroit (1941–1950) and considers his commitment to family life, naval service, and further training in art. I examine his role in the radical labor movement and his naval service in nearby Chicago, along with his art activities to promote social change and racial equality. Focusing on the later Detroit years (1950–1958), Chapter three merges the social history of Jim Crow, Detroit’s urban renewal programs, anti-communist scares, and HUAC hearings with an analysis of the imagery of Lee-Smith’s urban and seaside paintings to indicate the psychological tensions he experienced. Chapter four analyzes the impact of his relocation to New York City (1958–1968), a successful transitional period of his life during which he was buoyed by the Civil Rights Movement and gained the recognition he had sought. The Epilogue considers Lee-Smith between 1968 and 1999. By interpreting Lee-Smith’s art within an intimate, extensive biography, we see his world shaped by America’s history of race, poverty, and disenfranchisement. When the parallel histories of America and African America are analyzed together, the meaning of America and American art becomes enlarged and enriched.