"[This quote needs a citation] When Holiday recorded her previous album Lady in Satin with Ellis, she conveyed to him her desire to “sound like Sinatra”, but at the time was in such poor health from years of difficulty and substance abuse that a nurse sometimes had to help keep her propped up on a high stool as she sang.

[3] Billie Holiday was a departure from the stylings of her more string laden previous album, making use of a lighter string orchestra, minus the choir, and more horns, including a saxophone and a more jazz like feeling.

Songs like "All of You", "'Deed I Do", and "Baby Won't You Please Come Home" have a lighter and happier tempo and do not include strings.

Four days later, Billie Holiday's lifelong friend and music partner Lester Young died on March 15, 1959.

AllMusic music critic Ron Wynn stated, "In many ways, a sad event...