Billie Holiday (born Eleanora Fagan) was an American jazz singer and songwriter. She had a difficult childhood, which greatly affected her life and career. Much of her childhood is clouded by conjecture and legend, some of it propagated by her autobiography, Lady Sings the Blues, first published in 1956 and later revealed to contain many inaccuracies.

Her professional pseudonym was taken from Billie Dove, an actress she admired, and Clarence Holiday, her probable father. At the outset of her career, she spelled her last name "Halliday", presumably to distance herself from her neglectful father, but eventually changed it back to "Holiday".

There is some controversy regarding Holiday's paternity, stemming from a copy of her birth certificate in the Baltimore archives that lists the father as a "Frank DeViese". Some historians consider this an anomaly, probably inserted by a hospital or government worker.

Thrown out of her parents' home in Baltimore after becoming pregnant at thirteen, Billie's mother, Sadie Fagan, moved to Philadelphia where Billie was born. Mother and child eventually settled in a poor section of Baltimore. Her parents married when she was three, but they soon divorced, leaving her to be raised largely by her mother and other relatives.

At the age of 10, she reported that she had been raped. That claim, combined with her frequent truancy, resulted in her being sent to The House of the Good Shepherd, a Catholic reform school, in 1925. It was only through the assistance of a family friend that she was released two years later. Scared by these experiences, Holiday moved to New York City with her mother in 1928. In 1929 Holiday's mother discovered a neighbour, Wilbert Rich, in the act of raping her daughter; Rich was sentenced to three months in jail.

According to Billie Holiday's own account, she was recruited by a brothel, worked as a prostitute in 1930, and was eventually imprisoned for a short time for solicitation. It was in Harlem in the early 1930s that she started singing for tips in various night clubs. According to legend, penniless and facing eviction, she sang "Travelin All Alone" in a local club and reduced the audience to tears.

She later worked at various clubs for tips, ultimately landing at Pod's and Jerry's, a well known Harlem jazz club. Her early work history is hard to verify, though accounts say she was working at a club named Monette's in 1933 when she was discovered by talent scout John Hammond.

Hammond arranged for Holiday to make her recording debut on a 1933 Benny Goodman date, and Goodman was also on hand in 1935, when she continued her recording career with a group led by pianist Teddy Wilson. Their first collaboration included "What A Little Moonlight Can Do" and "Miss Brown To You", which helped to establish Billie Holiday as a major vocalist. She began recording under her own name a year later, producing a series of extraordinary performances with groups comprising the Swing Era's finest musicians.

Wilson was signed to Brunswick by John Hammond for the purpose of recording current pop tunes in the new Swing style for the growing jukebox trade. They were given free rein to improvise the material. Holiday's amazing method of improvising the melody line to fit the emotion was revolutionary (Wilson and Holiday took pedestrian pop tunes like "Twenty Four Hours A Day" or "Yankee Doodle Never Went To Town" and turned them into jazz classics with their arrangements). With few exceptions, the recordings she made with Wilson or under her own name during the 1930s and early 1940s are regarded as important parts of the jazz vocal library.

Among the musicians who accompanied her frequently was tenor saxophonist Lester Young, who had been a boarder at her mother's house in 1934 and with whom she had a special rapport. "Well, I think you can hear that on some of the old records, you know. Some time I'd sit down and listen to 'em myself, and it sound like two of the same voices, if you don't be careful, you know, or the same mind, or something like that."

Young nicknamed her "Lady Day" and she, in turn, dubbed him "Prez." She did a three-month residency at Clark Monroe's Uptown House in New York in 1937. In the late 1930s, she also had brief stints as a big band vocalist with Count Basie (1937) and Artie Shaw (1938).

The latter association placed her among the first black women to work with a white orchestra, an arrangement that went against the tenor of the times.