Originally published in 1939, Tobe is a children's book portraying the daily lives of an African American boy and his siblings on a small farm in rural North Carolina. The book was written by a white woman, Stella Sharpe Gentry, and illustrated by more than fifty staged photographs of actual rural children from the Greensboro area taken by Charles A. Farrell. In the spring of 2017, UNC Charlotte's Center for the Study of the New South and its Charlotte Teachers Institute hosted an evening of round table discussions to explore Tobe as a springboard into the many complex issues of representation, race, and identity that the book raises. Participants included educators, children's literature and African American culture specialists, and Charlotte community leaders who examined Tobe for its continuing cultural relevance. The discussion was led by Dr. Benjamin Filene, contemporary Tobe scholar and associate professor and director of public history at the University of North Carolina at Greensboro. This volume features essays from ten event participants focused on a variety of themes that emerged from the discussions.