Billie Holiday has been played on NTS over 90 times, featured on 80 episodes and was first played on 21 January 2013.

Billie Holiday (born Eleanora Fagan; April 7, 1915 – July 17, 1959) was an American jazz and swing singer. Nicknamed "Lady Day" by her friend and musical collaborator Lester Young, she played an important role in the development of jazz and popular singing. Holiday’s vocal style, influenced by jazz instrumentalists, introduced distinctive approaches to phrasing and tempo, and she was recognized for her expressive delivery and improvisational skill.

Holiday began singing in nightclubs in Harlem and was discovered by producer John Hammond, who encouraged her career. She signed a recording contract with Brunswick Records in 1935. Her work with Teddy Wilson produced the hit "What a Little Moonlight Can Do", which became a jazz standard. During the 1930s and 1940s, she recorded successfully for labels including Columbia and Decca. By the late 1940s, Holiday faced legal issues and struggles with drug abuse. After serving a brief prison sentence, she returned to perform a sold-out concert at Carnegie Hall, and she continued to perform successfully throughout the 1950s, including two additional sold-out shows at Carnegie Hall. Her final recordings, including the 1958 album "Lady in Satin", reflected changes in her voice and received mixed critical response, though they achieved modest commercial success. Holiday died on July 17, 1959, from cirrhosis and heart failure at the age of 44.

Holiday received posthumous recognition for her contributions to music, including four Grammy Awards for Best Historical Album. She was inducted into the Grammy Hall of Fame and the National Rhythm & Blues Hall of Fame. In 2000, she was also inducted into the Rock and Roll Hall of Fame as an early influence, with the institution noting that "Billie Holiday changed jazz forever". She has been named one of the 50 Great Voices by NPR and ranked fourth on Rolling Stone’s 2023 list of the "200 Greatest Singers of All Time". Several films have depicted her life, most recently "The United States vs. Billie Holiday" (2021).

Studio albums Billie Holiday Sings (1952) An Evening with Billie Holiday (1953) Billie Holiday (1954) Music for Torching with Billie Holiday (1955) Velvet Mood (1956) Lady Sings the Blues (1956) Body and Soul (1957) Songs for Distingué Lovers (1957) Stay with Me (1958) All or Nothing at All (1958) Lady in Satin (1958) Last Recording (1959)