Holiday was sent to Catholic reform school at the age of ten, after she admitted being raped. She was supposed to stay there for many years but a friend got her out only after two years. In New York, Holiday helped her mother with household work, but soon began working as a prostitute for the additional money.
Her big singing break came in 1933 when she auditioned for a dancing part at a speakeasy and a friend who was with her asked her if she could sing. In fact, Holiday sang at clubs all over New York City as early as 1930.
After recording a demo at Columbia Studios, Holiday joined a small group led by Goodman to make her debut on November 27, 1933 with 'Your Mother's Son-In-Law.'
During the last half of 1935, Holiday finally entered the studio again and recorded a total of four sessions.
With a pick-up band supervised by pianist Teddy Wilson, she recorded a series of songs. Holiday and various groups took old, unpopular songs like 'What a Little Moonlight Can Do,' 'Twenty-Four Hours a Day' and 'If You Were Mine' and made them great songs of the modern world. With Holiday's beautiful voice and the fashionable beat of her band, they skyrocketed to the top.
In late January 1937, she recorded several numbers with a small group called Count Basie's Orchestra. Tenor Lester Young and trumpeter Buck Clayton became especially close to Holiday.
After Holiday quit the band, she learned the song that would shoot her career to a new level. It was titled 'Strange Fruit.' This sad song was against the racism that still existed in the South. 'Strange Fruit' soon became the highlight of Billie’s performances. Milt Gabler signed her to record 'Lover Man,' a song written especially for her. This song soon became her third biggest hit.
Unfortunately, Holiday's troubles only continued after her release. Even though Holiday was overwhelmed with jazz, drugs, song publishing, and many other stresses, many of Holiday's recordings in the 1950’s were just as passionate as her standard work. During 1954, Holiday toured Europe and her 1956 autobiography brought her even more fame. During her final year, she made two more appearances in Europe before collapsing in May of 1959 of heart and liver disease.
While on her death bed, police found her in possession of heroin and as a result, she was arrested. Holiday died on July 17, 1959 in a private room located in New York City. Her system was completely unable to fight both withdrawal from the heroin and heart disease at the same time. Billie Holiday was a very strong woman with a very hard life; maybe her life was just a little too hard.