Nicknamed "Lady Day", Billie Holiday (1915-1959) was a popular jazz singer. Her early life was tragic and her drug abuse cut her life short, but she remains famous for her powerful yet vulnerable voice, her persona, and her fearless advocacy of civil rights with such songs as the anti-lynching ballad "Strange Fruit."

Notable for "Strange Fruit" (which took considerable balls considering this was way before the UsefulNotes/CivilRightsMovement), "Summertime" and "Easy Living".

!!Tropes found in Billie Holiday's life and works:

* BerserkButton: Racism seemed to be one.
* BrokenBird: Where to begin?
* FlowerInHerHair: Signature look. Many female singers since have copied it in order to pay tribute to her.
* TheLadette: Known for her love of drinking, brawling, and gambling.
* {{Mondegreen}}: "God Bless The Child"'s lines "Mama may have, Papa may have" could be heard as "Mama Mayhem, Papa Mayhem".
* ProtestSong: "Strange Fruit" was a early example and was daring for its time.
* RapeAsBackstory: By a neighbor at 10 years old.
* RetroactiveRecognition: Of a boy Billie occasionally babysat. He was a nephew of the man who ran her first record company, Commodore Records, and his name also happened to be Billy. He was a funny kid who grew up to be one Billy Crystal (of ''{{When Harry Met Sally}}'' fame).
* ToughActToFollow: Invoked. "Strange Fruit" was contractually required to be the last song Billie Holiday would ever perform in a night - no encores. Waiters would not serve patrons, and the only light would be a spotlight on Lady Day's face.