[3] Hopwood started out as a journalist for the Cleveland Leader as its New York correspondent, but within a year had his first play, Clothes (1906), produced on Broadway, with the aid of playwright Channing Pollock.

One play, The Demi-Virgin in 1921, prompted a court case because of its suggestive subject matter, including a risque game of cards, "Stripping Cupid".

[6] Although Hopwood announced to the press in 1924 that he was engaged to vaudeville dancer and choreographer Rosa Rolanda, Van Vechten confirmed in later years that it was a publicity stunt.

Famous Hopwood award winners include Robert Hayden, Marge Piercy, Arthur Miller, Betty Smith, Lawrence Kasdan, John Ciardi, Mary Gaitskill, Edmund White, Nancy Willard, Frank O'Hara, and Steve Hamilton.

Throughout his life, Hopwood worked on a novel that he hoped would "expose" the strictures the commercial theater machine imposed on playwrights, but the manuscript was never published.