Billie Holiday died penniless and alone, despite being one of the world's most influential jazz and blues singers. The performer rose to fame in the 1930s after releasing hits including Strange Fruit, I'll Be Seeing You, and Gloomy Sunday. Her unique and emotional vocal style helped cement her as one of the all-time greats. But behind closed doors, Holiday's life was marred with troubles.

She faced extensive racism throughout her career and entire life. Holiday wasn't allowed to enter venues through the front doors and experienced segregation in hotels and public accommodations. Holiday toured with Artie Shaw in 1938, becoming the first Black woman to front a white jazz ensemble. However, she had to find her own hotel to sleep in as she was barred from the ones the rest of the band stayed in.

The racism she faced was allegedly sparked from her performing Strange Fruit - a powerful song about the protest against the lynching of Black Americans.

Holiday battled with drug addiction throughout the duration of her career, which meant she was targeted by the US government, who reportedly launched a plan to destroy her career.

The Federal Bureau of Narcotics was led by alleged racist Harry J. Anslinger, who was particularly obsessed with controlling and punishing Black musicians. Holiday was a public figure who was bold and unbothered, but this immediately drew the attention of Anslinger.

Believing Holiday was setting a bad example, he placed surveillance on her. After performing at the Mark Twain Hotel in San Francisco in 1947, Holiday's home was raided.

She spent around one year in the Alderson Federal Prison Camp in West Virginia, having been originally arrested for possession of heroin. Holiday was released in 1948 for good behaviour, but faced ongoing harassment from the FBN. The musician struggled to regain her career, as the police had revoked her license needed to perform in clubs that served alcohol due to her criminal record.

Despite her health continuing to decline due to her drug use, Holiday still performed in concert halls.

In 1959, at the age of 44, Holiday was arrested and taken to Metropolitan Hospital in New York City. She died from complications related to liver and heart failure, brought on by her frequent alcohol and drug use. She was reportedly denied proper medical treatment in the final days of her life.

Holiday had been handcuffed to her bed and was under police guard in the days before her death. She died alone, with reportedly just 70 cents in her bank account, marking a devastating end to one of the greatest jazz singers in history.