Gwendolyn Bennett was born on July 8, 1902, in Giddings, Texas, to Joshua Robin and Mayme (née Abernathy). Bennett spent her early childhood in Washington, D.C. Her parents divorced when she was around four. Joshua kidnapped Bennett in 1910. Father and daughter lived on the run for a lengthy period, moving between Washington, D.C., Pennsylvania, and New York. Bennett had no further contact with her mother until she was an adult. She attended Brooklyn Girl’s High School and graduated in 1921. Bennett then enrolled at Columbia University’s Teachers College, while also studying in the university’s fine arts department. After two years at Columbia, Bennett transferred to the Pratt Institute.
Bennett published her first poem, “Nocturne,” in the November 1923 issue of Opportunity magazine. She also designed the magazine cover for the Crisis’s December 1923 issue. From 1924 to 1927, she taught art at Howard University, but took a year-long leave in 1925 to study art in Paris on a scholarship. Bennett’s father died on August 13, 1926, shortly after her return from Paris, from a probable suicide. He had been charged with fraud and embezzlement shortly before his death. That summer, Bennett began to design and edit a weekly literary news column for Opportunity. She was forced to resign from Howard, however, in 1927 after she became engaged to a medical student. She next studied art with painter Aaron Douglas at the Alfred C. Barnes Foundation and, after moving to New York, organized a literary society at the 135th Street Branch of the New York Public Library (now, the Countee Cullen Library) that included head librarian, Ernestine Rose, and Crisis contributor Jessie Redmon Fauset. Bennett was also a contributor and co-editor for Fire!! magazine. Bennett published over twenty poems in the 1920s. She also completed a great deal of artwork, much of which was destroyed in two fires—one at Bennett’s mother-in-law’s home in 1926, and another at her stepdaughter’s home in the early 1980s.
In 1928, Bennett relocated to Eustis, Florida, with her first husband, Alfred J. Jackson, and stopped writing her column. She ceased to publish for several years. Instead, she taught art and Spanish at a local high school. During this 1930s, she struggled with alcoholism. Bennett returned to New York, settling in Hempstead, in 1932. She worked odd jobs before taking a post with the Works Progress Administration (WPA) Art Project from 1935–41. In 1936, she directed the Harlem Arts Guild. In 1940, she married Richard Crosscup, a white Harvard graduate and fellow teacher. She was suspended from her post at the Harlem Art Center after coming under scrutiny from the House Un-American Activities Committee (HUAC). Bennett remained an object of the committee’s scrutiny well into the 1950s. From 1948 to 1968, she worked for the Consumers Union, until she and Crosscup decided to open and operate an antiques shop in Pennsylvania.
Bennett died on May 31, 1981, in Reading, Pennsylvania. She survived her second husband by one year.