In 1922, Drewry began working as a railroad statistician for Norfolk and Western Railway through a friend's recommendation.
Drewry continued writing for various magazines, including Virginia Quarterly Review, The New York Times, and The Nation.
[4] The two had two children, a daughter, Barbara Louise Anderson, and a son, Guy Carleton ″David″ Drewry Jr.
Drewry published his final work To Love That Well in 1975, which was a compilation of poems in past novels and publications.
Drewry often takes a position of authority in his poems, attempting to explain to the reader how the world operates.