Billie Holiday in 1949, photographed by Carl Van Vechten
Born Eleanora Fagan Goughy but also known as 'Lady Day', she had a difficult childhood which affected her life and career. Much of Holiday's childhood is clouded by conjecture and legend, some of it propagated by herself in her autobiography published in 1956. She was born in Philadelphia but grew up in the Fells Point section of Baltimore, Maryland. According to her autobiography, her house was the first on their street to have electricity. Her mother, Sadie Fagan, was allegedly only thirteen at the time of her birth; her father Clarence Holiday, a jazz guitarist who would play for Fletcher Henderson, was fifteen. According to Billie Holiday's autobiography, her parents married when she was three, but they soon divorced, leaving her to be raised largely by her mother and other relatives. A hardened and angry child, she dropped out of school at an early age and began working as a prostitute with her mother. This preceded her move to New York with her mother sometime in the early 1930s.
There is controversy regarding Holiday's paternity. This stems from a copy of her birth certificate in Baltimore archives that lists the father as a "Frank DeViese." Some historians consider this an anomaly, probably inserted by a hospital or government worker (See Donald Clarke, Billie Holiday: Wishing on the Moon, ISBN 0306811367). Clarence Holiday accepted paternity, but was hardly a responsible father. In the rare times she did see him, she would shake him down for money by threatening to tell his then-girlfriend that he had a daughter.
Early career successes
Settling in Harlem, Holiday began singing informally in numerous clubs. Around 1932 she was "discovered" by record producer John Hammond at a club called Monette's (there is still some dispute among historians about who was the first to hear and publicise her, although it is generally agreed that Hammond was the first.) Hammond arranged several sessions for her with Benny Goodman; her first-ever recording was "Your Mother's Son-In-Law" (1933).
It was around this time that Holiday had her first successes as a live dancer. On November 23, 1934, she performed at the Apollo Theater to glowing reviews. The performance, with pianist (and then-lover) Bobby Henderson, did much to solidify her standing as a jazz and blues singer. Shortly thereafter, Holiday began performing regularly at numerous clubs on 52nd Street in Manhattan.
Compared to other jazz singers, Holiday had a rather limited range of just over an octave. She more than compensated for this shortcoming, however, with impecable timing, nuanced phrasing, and emotional immediacy.
She later worked with such legends as Lester Young, Count Basie, and Artie Shaw, breaking the color barrier along the way by becoming one of the black jazz singers of that era to perform with white musicians. Nevertheless, she was still forced to use the back entrance and forced to wait in a dark room away from the audience before appearing on stage. Once before an audience, she was transformed into Lady Day with the white gardenia in her hair. She explained the sense of overpowering drama that featured in her songs, saying "I've lived songs like that." and she had.
Later life and death
Holiday was a dabbler in recreational drug use for most of her life, smoking marijuana, by some accounts, as early as twelve or thirteen years of age. However, it was heroin that would be her undoing. It is unclear who first introduced Holiday to the drug, but there is consensus from historians and contemporaneous sources that she began intravenous use sometime around 1940.
Holiday's success was marred by this growing dependence on drugs, including alcohol, and abusive relationships. This affected her voice as well, and in her later recordings her youthful spirit was replaced by overtones of regret. Her impact on other artists was undeniable, however; even after her death she influenced such singers as Janis Joplin and Nina Simone. In 1972, Diana Ross played her in a movie version of Holiday's autobiography, Lady Sings the Blues. To everyone's surprise, the film was a commercial smash and earned a Best Actress nomination for Ross. In 1987 U2 released "Angel of Harlem", a tribute to her.
Her personal life was as turbulent as the songs she sang. She married trombonist Jimmy Monroe on August 25, 1941. While still married to Monroe, she took up with trumpeter Joe Guy as his common law wife. She finally divorced Monroe in 1947 as she split with Guy. On March 28, 1952, Billie married Louis McKay, a Mafia "enforcer." McKay, like most of the men in her life, was abusive, but did try to get her off drugs. They were separated at the time of her death. Holiday was also rather openly bisexual and was rumored to have had several affairs with notable stage and film actresses, including Tallulah Bankhead.
Her late recordings on Verve are as well remembered as her Commodore and Decca recordings of 20 years before. Several of her songs, including her signature song "God Bless the Child", George Gershwin's "I Love You Porgy" (covered exactly by Simone), and the rueful blues "Fine and Mellow" are jazz classics. Her performance of "Fine and Mellow" on CBS's The Sound of Jazz program is memorable for her interplay with her long-time friend Lester Young; both were less than two years from death.
Her performance of Abel Meeropol's anti-lynching song on Commodore, "Strange Fruit," with the lyric "Southern trees bear a strange fruit" gave her a place, not just in musical history, but in American history as well. 
She was arrested for heroin possession in May 1947 and served eight months of a year-and-a-day sentence at the Alderson Federal Correctional Institution for Women in West Virginia. Her New York City Cabaret Card was subsequently revoked, which kept her from working in clubs there for the remaining 12 years of her life.
Following a highly successful European tour in 1954, Holiday toured the continent again from late 1958 to early 1959. While in London in February 1959, Holiday made a memorable televised appearance on the BBC's Chelsea at Nine, singing, among other songs, "Strange Fruit." Holiday made her final studio recordings (with Ray Ellis and his Orchestra, who had also recorded her Lady in Satin album the previous year — see below) for the MGM label in March 1959 (included in her complete Verve recordings collection.) These final studio recordings were released posthumously on a self-titled album, later re-titled and re-released as Last Recordings. She made her final public appearance at a benefit concert at the Phoenix Theater in Greenwich Village, New York City on May 25, 1959. According to the masters of ceremony at that performance, Leonard Feather (a renowned jazz critic) and Steve Allen, she was only able to make it through two songs, one of which was "Ain't Nobody's Business If I Do."
On May 31, 1959, she was taken to Metropolitan Hospital in New York, suffering from liver and heart problems. On July 12, she was placed under house arrest at the hospital for possession, despite evidence suggesting the drugs may have been planted on her. Holiday remained under police guard at the hospital until she died from cirrhosis of the liver on July 17, 1959 at the age of 44. In the final years of her life, she had been progressively swindled out of her earnings, and she died with only $0.70 in the bank and $750 on her person.
Billie Holiday is interred in Saint Raymond's Cemetery, Bronx, New York.
While instantly recognizable, Holiday's voice changed over time. Her first recordings in the mid-1930s featured a bouncy, girlish voice. By the early 1940s her singing became informed by her acting skill. It was during this time when she recorded her signature songs "Strange Fruit" and "I Cover the Waterfront". Many called her voice lovingly sweet, weathered and experienced, sad and sophisticated. As she aged, the effects of her drug abuse continued to ravage her range and her voice changed considerably, becoming somewhat rougher. Her last major recording, Lady in Satin, was released in 1958 and reveals a woman with an extremely limited range, but wonderful phrasing and emotion. The recording featured a backing from a 40-piece orchestra conducted and arranged by Ray Ellis, who said of the album in 1997:
I would say that the most emotional moment was her listening to the playback of "I'm a Fool to Want You." There were tears in her eyes...After we finished the album I went into the control room and listened to all the takes. I must admit I was unhappy with her performance, but I was just listening musically instead of emotionally. It wasn't until I heard the final mix a few weeks later that I realized how great her performance really was.