Gwendolyn Bennett, black writer and artist, was born in Giddings, Texas, on July 8, 1902, the only child of Joshua Robin and Mayme Frank (Abernathy) Bennett. She spent only one year in Texas. Her paternal grandfather, R. B. Bennett, had come from North Carolina on a wagon train and was a small rancher and then a barber in Giddings. Her father had been a principal in a Gonzales, Texas, black high school from 1901 to 1903. In 1903 he moved his family to Wadsworth, Nevada, where he and his wife taught in the Indian Service for the Bureau of Indian Affairs. Gwen Bennett's earliest memories were of life on this Paiute Indian reservation. In 1906 the Bennetts moved to Washington, D.C., where he worked as a clerk for the Bureau of Indian Affairs and enrolled in the Howard University School of Law. He obtained his law degree in 1908. His wife filed for divorce in 1910 and was awarded custody of Gwendolyn. Joshua subsequently kidnapped Gwendolyn and took her with him as he moved from Washington to Pennsylvania and, finally, to Brooklyn, New York. There, Gwendolyn Bennett came of age at the start of the Harlem Renaissance.
In her childhood she had recited long poems to appreciative adults and painted well. She attended Girls' High School in Brooklyn, where she became the first African American in the school's literary and drama societies; she also won first place in an art contest. Subsequently, she attended Columbia University (1921) and then Pratt Institute (1922–24), studying art education. During this time she began publishing. In December 1923 Opportunity, the official organ of the National Urban League, accepted her poem "Heritage," and The Crisis, the official organ for the National Association for the Advancement of Colored People, carried her cover illustration. From 1923 to 1931 Bennett's poetry periodically appeared in The Crisis, Opportunity, Psalms, and The Gypsy, and several anthologies. During this same period she produced five journal cover illustrations. In 1926 Fire!!, a small arts magazine begun by African-American artists Langston Hughes, Wallace Thurman, Bruce Nugent, and Gwen Bennett, among others, carried "Wedding Day," her first published story. Her second story, "Tokens," appeared in Charles S. Johnson's Ebony and Topaz (1927).
She accepted a position as instructor at Howard University in 1924, teaching design, watercolor, and crafts. She received a fellowship to study art in Paris in 1925 and at the Barnes Foundation in Marion, Pennsylvania, in 1927. Also in 1927 she married Dr. Alfred Joseph Jackson, who had been an intern at Freedman's Hospital, Howard University. The young couple moved to Eustis, Florida, where they resided until the early 1930s, when they returned to New York.
Jackson died in 1936 and Bennett remarried in 1940, when she met Richard Crosscup, a literature teacher and social activist. Their interracial marriage was not a socially accepted union. In 1935 Bennett joined the Harlem Artists Guild; from 1939 to 1944 she directed the Harlem Community Art Center but was suspended for her political convictions. In the early 1940s she served on the board of the Negro Playwright's Guild, and she directed the development of the George Washington Carver Community School. She was one of the most versatile figures to participate actively both in the 1920s arts movement known as the Harlem Renaissance and in the 1930s arts alliance formed among African-American graphic artists called the Harlem Artists Guild.
Gwendolyn Bennett never returned to Giddings. She retired from public life in the 1940s but remained in New York until 1968. Through the 1950s to the mid-1960s she worked for the Consumers Union. When she retired from this agency, she and her husband moved to Kutztown, Pennsylvania, where she had established an antique store. On January 9, 1980, Richard Crosscup died of sudden heart failure. His wife died on May 30, 1981, in the Reading County Hospital.