Billie Holiday, one the greatest singers America has produced, and certainly one of just a handful of the best jazz or pop singers who ever graced a microphone, led a famously flawed and tragic life. Sexually abused, and addicted to multiple drugs including heroin, she managed to transcend race, stylistic limitations and negative experience to create the 20th century’s most memorable interpretive vocals. Whether singing pop tunes, the occasional purpose-built feature number or even throwaway blues ditties, her best recordings remain among the most important in modern music. First with Count Basie’s groundbreaking late 1930’s band, and then with Artie Shaw’s Orchestra, she began to make a name for herself both with these bands, and through a series of seminal recordings under Teddy Wilson’s leadership. The best of the latter records feature Lester Young’s unusually sympathetic saxophone as a contrapuntal voice. After 1940, she performed as a featured act, backed by various small groups in theaters and clubs around the country. She had recorded some material under her own name for Milt Gabler’s small Commodore Records label, but he eventually managed to get her a contract with much larger Decca Records. Her recording of “Travelin’ Light”, along with the earlier “Strange Fruit” and “God Bless the Child,” allowed her to become at least a fringe player in the celebrity mainstream. Her addictions and abuses worsened as the decade unfolded, but as of 1942, she was still in good voice and performing frequently. In August of that year, she was booked into Chicago’s Garrick Stagebar, a fairly swanky downtown nightclub in the heart of the loop. Backed by Henry “Red” Allen’s great little band, her engagement there was extended several times as summer turned to fall. She died tragically but inevitably in 1959, just 44 years old. The poster here is a re-imagining of how a promotional handbill might have appeared during that 1942 Chicago engagement.