Synopsis
In 1957, Billie Holiday meets with a radio journalist, Reginald Lord Devine, for an interview. He asks her what it is like to be a "colored woman" and about the trouble she keeps getting into because of her hit song "Strange Fruit". Billie says it is about human rights, something the government often forgets.
In 1947, Billie's husband Monroe and her manager Joe Glaser try to get Billie to cut "Strange Fruit" from her set list, saying people high up in the government do not want to hear her sing it. Lester Young, Billie's sax player, supports her in playing it.
FBI agent Harry J. Anslinger tells other agents that Billie is a threat, her song promotes the wrong ideas, and she has not stopped singing it. Unable to arrest her for singing, they decide to go after her on drug charges. After Billie's next show, Agent Jimmy Fletcher, disguised as a soldier, witnesses her doing drugs. The FBI arrest Billie and her lover Joe Guy for drug use and possession. The judge sentences Billie to a year in jail. It is later revealed that Anslinger paid off Guy.
Anslinger tells Jimmy that they need to make sure Billie never sings again. Jimmy questions why Billie is such a problem. Anslinger tells Fletcher to go to the prison to get back in with Billie. Instead, he tells her to not trust anyone and warns her the FBI will continue to try to set her up.
After Billie is released from prison, she does a Carnegie Hall show, where an audience member asks her to sing "Strange Fruit" and she sadly declines. Billie meets John Levy, who tells her that he will pay off the right people to make sure she can keep singing in his clubs. They begin a relationship. Levy proposes to her, then slips drugs into her pocket just in time for the FBI to enter. In court, Fletcher admits that Billie was possibly framed, and she is freed. Anslinger sends Fletcher to follow Billie on her tour.
In 1949, Jimmy comes to see Billie after a successful tour stop and tells her the agency wants her to think he was fired. Suspicious, the whole crew has Jimmy do heroin to show he can be trusted. Over the course of the tour, Jimmy and Billie fall in love. One day, after the bus breaks down, Billie breaks up with Jimmy, telling him he needs to find a nice girl, and that is not her. Jimmy returns to work, where he finds he has been replaced.
Billie marries Louis McKay, later returning to Jimmy. Later, Billie tells Jimmy she has liver failure. In the hospital, Anslinger tells Billie and McKay that if she cooperates, she will never see them again. Billie tells him that his grandkids will be singing "Strange Fruit" one day.