His carvings reflected everyday themes and shared values of the Black culture in the segregated Southern United States in the early 20th century.

[2] After graduating from VUU in June 1924 Bolling began working as a porter at the Everett Waddey Company stationery store.

Reportedly he enjoyed whittling which would have provided him significant experience with carving various kinds of wood.

[4] His hobby seems to have taken a serious turn about the time he produced some early figures for a group exhibition sponsored by the YWCA.

[4] About 1928 these first figures attracted the interest of Carl Van Vechten, a patron of the Harlem Renaissance movement.

[1]: 38, 281 [6] His work began to achieve broader recognition as a result of the National Negro Exhibition of 1933 at the Smithsonian.

[1]: 38 [4] Bolling participated in a number of art tours between 1934 and 1940, managed by the Harmon Foundation to showcase the artistic work of African-Americans.

This was followed by a show at the William D. Cox Gallery in New York in June 1937 of 17 pieces including the recently completed sculpture series Days of the Week which he had begun in 1933.

In 2006, the Library of Virginia produced an exhibition of Bolling's work and included material related to 30 of his pieces.