Final answer:
Billie Holiday was the first black woman to sing with a white orchestra and tour the segregated South with a white bandleader.
Step-by-step explanation:
The first black woman to sing with a white orchestra and tour the segregated South with a white bandleader was Billie Holiday.
She was a renowned jazz singer who gained popularity in the 1930s and 1940s. Despite facing racial discrimination, Holiday's talent and success broke barriers in the music industry.