This chapter traces the career of Henry Blake Fuller from the 1890s through the opening of the twentieth century. Fuller, a scion of one of the city’s first families and student of Chicago’s social networks and institutions, began by writing travel romances set in the Italian past. Turning quickly to literary realism, he depicted the rapidly expanding city of his birth, becoming arguably the first Midwestern writer to set his novels in the tumultuous environment of the growing metropolis. Fuller’s novels The Cliff-Dwellers (1893) and With the Procession (1895) were unvarnished critiques of Chicagoans’ materialist priorities, social ambitions, and unethical business practices, as well as the psychological and communal fractures caused by the accelerated pace of the city. Applying the structural principles of architecture to new methods of narration, Fuller’s novels of this period represent stylistic and conceptual differences between his practice of realism and that of his better-known contemporaries. The chapter also discusses Fuller’s long-standing interest in the Chicago art scene in books like Under the Skylights (1901), in which art and commerce struggle for primacy.