Despite possessing more qualifications than necessary, she was promptly turned away and barred from enrollment as the school would not officially accept African-American graduate students until 1948.

[1] On several occasions in her later years, Holliman's work was published in Proud magazine, a publication that addressed the needs of St. Louis' black community from 1971 until 1981.

[1] Jessie Housley Holliman taught visual arts to students at the Divoll Elementary School on Dayton Avenue in St. Louis for more than thirty–nine years.

Holliman was known to be friends with numerous local artists and educators, including Julia Davis and Frederick Cornelius Alston.

For the exhibition titled, "Paintings and Sculpture by Negro Artists in St. Louis and Elsewhere" (April–May 1949), the Homer G. Phillips Hospital lent its portrait of the institution's namesake, a prominent lawyer and politician.

The Urban League of St. Louis hired her to paint a large mural titled Racial and Industrial Harmony, which has since been destroyed as the building was demolished.

[11] The building was designed by the Eames & Young architecture firm with assistance from architect Albert B. Groves in 1926, and it was declared a historic city landmark in 1976.

[14] In 1936, Jessie's pencil lithograph Left–Handed Ironer was awarded the grand prize in the Seventh Annual Art Exhibit of the St. Louis Urban League.

The exhibition was held in the Arts and Crafts Hall of one of the largest department stores in St. Louis, Stix Baer & Fuller, where it was viewed by hundreds of both black and white visitors.

[2] In addition to sharing Holliman's work, Opportunity regularly featured the art of many other prominent African-American women like Mary Tarleton Knollenberg, Georgette Seabrooke, Louise E. Jefferson, and Gwendolyn Bennett.