Question: "Who was the first black singer with a big time white band?"
Answer: Most jazz historians believe Billie Holiday was the first when she joined Artie Shaw's Orchestra as lead vocalist. She began singing with the group in 1938. Despite the continuing support of the entire band, however, show promoters and radio sponsors soon began objecting to Holiday -- based on her unorthodox singing style almost as much as her race. After a series of escalating indignities, Holiday quit the band in disgust.
Here is Billie singing the great standard "I Can't Get Started (with you)"