In Baltimore he attended a boys school with the banjo player Elmer Snowden. Both of them played banjo with various Baltimore jazz bands, including the band of Eubie Blake. At the age of 16, Holiday became the unmarried father of Billie Holiday, who was born to 13-year-old Sadie Harris. He rarely visited Harris or her daughter. He moved from Baltimore to Philadelphia when he was 21 years old.
Holiday died in 1937. He had been exposed to mustard gas while serving in World War I. He fell ill with a lung disorder while on tour in Texas and was refused treatment at a local hospital. By the time he was able to receive care in the Jim Crow ward of the Veterans Hospital, pneumonia had set in, and he died shortly after. Two years later Billie Holiday recorded the song “Strange Fruit.” She said that the song reminded her of the death of her father after he was denied medical treatment.
Holiday played rhythm guitar and banjo as a member of the Fletcher Henderson Orchestra (1928–33). He also recorded with Benny Carter (1934) and Bob Howard (1935) and worked with Charlie Turner (1935), Louis Metcalf (1935–36), and the Don Redman Big Band (1936–37).
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