Billie Holiday ("Lady Day") is considered by many to be the greatest of all jazz singers. In a tragically abbreviated singing career that lasted less than three decades, her evocative phrasing and poignant delivery profoundly influenced vocalists who followed her. Although her warm, feathery voice inhabited a limited range, she used it like an accomplished jazz instrumentalist, stretching and condensing phrases in an ever-shifting dialogue with accompanying musicians. Famous for delivering lyrics a bit behind the beat, she alternately endowed them with sadness, sensuality, languor, and irony. Rarely singing blues, Holiday performed mostly popular material, communicating deep emotion by stripping down rather than dressing up words and lines. "If you find a tune that's got something to do with you, you just feel it, and when you sing it, other people feel it, too," Holiday once explained. According to the Penguin Encyclopedia of Popular Music, "She was the first and is perhaps still the greatest of jazz singers, if the essence of jazz singing is to make the familiar sound fresh, and to make any lyric come alive with personal meaning for the listener."
Holiday's life was a study in hardship. Her parents married when she was three, but her musician father was seldom present and the couple soon divorced. Receiving little schooling as a child, Holiday scrubbed floors and ran errands for a nearby brothel so she could listen to idols Louis Armstrong and Bessie Smith on the Victrola in its parlor. Brutally raped at ten, she was sent to a reformatory for "seducing" her adult attacker; at fourteen she was jailed for prostitution. Determined to find work as a dancer or singer in Harlem, Holiday moved to New York City in 1928 and landed her first job at Jerry Preston's Log Cabin, where her vocals moved customers to tears. Discovered in another Harlem club by jazz record producer John Hammond in 1932, she made her first recording a year later with Benny Goodman's orchestra. She began to record regularly for Columbia, usually under the direction of Teddy Wilson, backed by small studio bands comprised of the day's best jazz sidemen. These included saxophonist and soulmate Lester Young, whose style approximated Holiday's own; it was he who gave the pretty, dignified young singer the nickname "Lady Day."
Intended largely for a black jukebox audience, the Wilson discs were quickly and cheaply made. But Holiday and company transformed them into jazz treasures, immediately appreciated by musicians, critics, and jazz afficianados, if not the public at large. These hundred-odd songs—delivered in a light, bouyant style—are today considered among Holiday's most significant work. Forgoing club engagements in l937 to tour with Count Basie's orchestra, Holiday went on to become one of the first black vocalists to be featured with a white band when she fronted for Artie Shaw a year later. Life on the road proved bitter for the singer, though; racial segregation made simple things like eating, sleeping, and going to the bathroom logistically difficult. Fed up when she could not enter one hotel through the front door with the rest of the Shaw orchestra, Holiday abandoned touring, returning to New York clubs and cabarets as a solo artist.