Heyward also wrote poetry and other novels and plays, as well as the children's book The Country Bunny and the Little Gold Shoes (1939).

[3] He was a descendant of Judge Thomas Heyward, Jr., a South Carolinian signer of the United States Declaration of Independence, and his wife, who were of the planter elite.

Although described as a derivative work that reportedly showed little promise, Heyward was encouraged enough to pursue a literary career.

During this period Heyward and his friend Henry T. O'Neill together operated a successful insurance and real estate company.

By 1924, Heyward had achieved a measure of financial independence, allowing him to give up business and devote himself full-time to literature.

Between stints of writing, he supplemented his income by lecturing on southern literature at colleges and the Porter Military Academy.

Heyward wants Charleston and its African-American residents to stay just as they are.... Linguistically marking all of the novel's African-American characters as uneducated and even illiterate is just one among many racial stereotypes.... "[S]outhern whites took care of southern blacks without interference or any systematic attempt to lift African Americans beyond their lowly status.

[10]For the opera Porgy and Bess, both Heyward and Ira Gershwin, the composer's brother and regular partner, worked on the lyrics.

In his introduction to the section on DuBose Heyward in Invisible Giants: Fifty Americans Who Shaped the Nation But Missed the History Books (2003), Stephen Sondheim wrote: DuBose Heyward has gone largely unrecognized as the author of the finest set of lyrics in the history of the American musical theater – namely, those of 'Porgy and Bess'.

His work is sung, but he is unsung.The Gershwin opera Porgy and Bess was produced in 1935, featuring top African-American singers and chorus.

Heyward continued to explore Black Charleston with another novel set in Catfish Row, Mamba's Daughters (1929).

The play addressed issues of mixed-race, featuring a couple in a small southern town who have grown up believing they were white and learning about some African-American ancestry.

It was described as "singularly charming and very original", covering their and friends' interpretations of "the relations of men and women".