For some reason I was drawn to a post I wrote a few years ago, Lester Young & Billie Holiday: The Krishna and Radha of jazz, which inspired me to play an MP3 playlist comprised of this box set I ripped to my player: Billie Holiday: Lady Sings the Blues box set
See my review on the page linked to for a complete track listing.
A reasonably decent documentary is Masters of American Music: Lady Day - The Many Faces of Billie Holiday:
That video is part of a value-priced set titled Masters of American Music, which I highly recommend. See my review on that page for why.
This BBC documentary is excellent as well and openly discusses Billie's life, both good and bad, as well as her music:
I'll end this post with what is currently playing in the background as I write this entry (from 1935 - see this story):
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