She attended Cass Technical High School,[13] where fellow students included such future musical talents and jazz greats as Donald Byrd, Gerald Wilson, and Kenny Burrell.

While in high school, she tried her hand at a number of instruments including the saxophone and string bass before, influenced by her father and piano teacher, coming upon the harp.

Instructed by Velma Froude, Ashby learned the strict classical style of harp playing influenced by French harpist Carlos Salzedo.

Ashby overcame their initial resistance and built support for the harp as a jazz instrument by organizing free shows and playing at dances and weddings with her trio.

[15] She recorded with Jimmy Cobb, Ed Thigpen, Richard Davis, Frank Wess and others in the late 1950s and early 1960s.

Her next album Hip Harp (1958), on Prestige, featured Frank Wess on flute, Herman Wright on bass, and Art Taylor on drums.

[20] In the 1960s, Ashby, together with her husband, formed a theatrical group to produce plays that would be relevant to the African-American community of Detroit.

Later in her career, she would make recordings and perform at concerts primarily to raise money for the Ashby Players theatrical productions.

In the late 1960s, the Ashbys gave up touring and settled in California, where Dorothy broke into the studio recording system as a harpist through the help of the soul singer Bill Withers, who recommended her to Stevie Wonder.

[23] In 2018, Drake included a sample of Ashby's rendition of "The Windmills of Your Mind" in his song "Final Fantasy" from the album Scorpion.