South African artist Irma Stern (1894–1966) is one of the nation’s most enigmatic modern figures. Stern held conservative political positions on race even as her subjects openly challenged racism and later the apartheid regime. Using paintings, archival research, and new interviews, this book explores how Stern became South Africa’s most prolific painter of Black, Jewish, and Colored (mixed-race) life while maintaining controversial positions on race. Through her art, Stern played a crucial role in both the development of modernism in South Africa and in defining modernism as a global movement. Spanning the Boer War to Nazi Germany to apartheid South Africa and into the contemporary #RhodesMustFall movement, Irma Stern’s work documents important twentieth-century cultural and political moments. More than fifty years after her death, Stern’s legacy challenges assumptions about race, gender roles, and religious identity and how they are represented in art history.