Modern literature frequently evokes Toronto. The city is prominent in the poetry of Dennis Lee and Dionne Brand, and the novels of Michael Ondaatje, Anne Michaels, Margaret Atwood, or Emily St. John Mandel. A boom in Canadian literary criticism focusing on the city reflects this prominence. However, only recently has critical attention turned to the Canadian city’s literary past. This article reopens the history of Toronto’s literary histories, re-examining moments in the twentieth century when the city’s literature has been appraised. Drawing on the work of Tony Kilgallin, Isabelle Hughes, William Kilbourn, book reviews, and archival papers from the Toronto Book Awards, it looks at the critical evolution of how Toronto has been represented in both national and civic literature. It also examines literary figures once championed but now out of print and seldom read, considering how and why certain literary evocations of Toronto have endured.