Shirley Horn began playing piano at an early age, and had thoughts as a teenager of becoming a classical artist. She was offered a scholarship to Juilliard, but turned it down for financial reasons. She then became enamored with the famous U Street jazz area of Washington (largely destroyed in the 1968 riots), sneaking into jazz clubs before she was of legal age.

Horn first achieved fame in 1960, when Miles Davis "discovered" her. Davis` praise had particular resonance in two respects, one because he was so highly respected as a musician, and two because he rarely had anything positive to publicly offer about any musician at that time. Shirley had, though, recorded several songs with violinist Stuff Smith in 1959 both as a pianist and a singer. After her discovery by Davis, she recorded albums on different small labels in the early 1960s, eventually landing contracts with larger labels Mercury Records and Impulse Records. She was popular with jazz critics, but did not achieve significant popular success.

Quincy Jones attempted to make Horn into a pure vocalist in several recording sessions, something he later hinted may have been a mistake. Horn was also disturbed by the changes in popular music in the 1960s following the arrival of The Beatles, and stated "I will not stoop to conquer" in largely rejecting efforts to remake her into a popular singer. From the late-1960s, she concentrated on raising her daughter Rainy with her husband, Shepherd Deering (whom she had married in 1955) and largely limited her performances to her native Washington, D.C., while she often worked full-time as an office worker.

Once her family was grown, she began touring more widely from 1978 onwards. She is best known for her recordings with Verve Records since 1987. Horn was nominated for nine Grammy Awards during her career, winning in 1999 for Jazz Vocal Album for I Remember Miles, a tribute to her friend and encourager.

Preferring to perform in small settings, as with her trio, she recorded with orchestra too, as on the 1992 album Here`s to life, which is highly rated by her fans, the title song being generally considered as her signature song. Arranger Johnny Mandel won the Grammy Award for Best Instrumental Arrangement Accompanying Vocal(s) for that album. A video documentary of Horn`s life and music was released at the same time as "Here`s To Life" and shared its title. At the time Mandel commented that Horn`s piano skill was comparable to that of the noted jazz great Bill Evans. A follow-up was made in 2001, named You`re My Thrill.

Shirley Horn kept for twenty five years the same rhythm section: Charles Ables (bass) and Steve Williams (drums). Don Heckman wrote in the Los Angeles Times (February 2, 1995) about "the importance of bassist Charles Ables and drummer Steve Williams to the Horn`s sound. Working with boundless subtlety, following her every spontaneous twist and turn, they were the ideal accompanists for a performer who clearly will tolerate nothing less than perfection".

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