(Credit: William P. Gottlieb)

Six definitive songs: The ultimate beginner's guide to Billie Holiday

Looking back at the astounding career of Billie Holiday, it seems she often used the pain she endured as fuel for her deeply moving performances. Through a tumultuous childhood raised by her young mother to a drug-riddled career, Holiday defied societal expectations of what a young black woman could accomplish, especially one with as unique a voice and personality as hers. 

Among the childhood chaos, Holiday found solace in singers like Bessie Smith and Louis Armstrong. When she moved to New York City in the late 1920s with her mother, she began singing in local clubs, creating a new persona called “Billie” after the film star Billie Dove, striving for the same path as her idols. After establishing herself as a unique voice in the jazz scene, Holiday caught the attention of legendary musicians throughout her career and ended up working with Duke Ellington, Lester Young, and even appeared with her idol Louis Armstrong in the 1947 film New Orleans.

Although her hard-partying ways took a toll on her once velvety voice (she would eventually succumb due to complications from a cluster of longstanding addictions) it only added to the richness of her lyrics and elevated her mystic in the genre-defying evolution as a singer. Right before her passing, Holiday released a shocking autobiography titled Lady Sings the Blues, which established her as a cultural icon. Today, Billie Holiday is still adored for her creative musical masterpieces, and fearless views on inequality and justice, among many other things.

“If you find a tune and it’s got something to do with you, you don’t have to evolve anything,” Holiday once said, adding: “You just feel it, and when you sing it other people can feel something too.” With her soulful renditions of classics, this can be said about the evocative, fervent voice in which she turned any song she sang into her own. While it’s impossible to limit someone with that amount of range and expansion, here are the six definitive songs of Billie Holiday’s short-lived—  but immensely impactful— career. 

Billie Holiday’s six definitive songs:

Riffin’ The Scotch’ (1933)

At the age of 18, Holiday was performing regularly at jazz clubs around Harlem, and one night while performing, was discovered by producer John Hammond. From that moment on, Hammond was instrumental in providing recording opportunities with Holiday and eventually connected her with rising-superstar himself, clarinettist, and bandleader Benny Goodman. 

From that first meeting, Hammond was impressed by Holiday’s singing style, and from their mutual admiration came the song ‘Riffin’ The Scotch’, which sold 5,000 copies and very quickly Holiday on the map. Hammond later said: “Her singing almost changed my music tastes and my musical life, because she was the first girl singer I’d come across who actually sang like an improvising jazz genius.” 

‘Summertime’ (1936)

In September of 1936, Billie Holiday’s rendition of ‘Summertime’ hit the US pop charts at number 12, the first version to do so. The original song was composed in 1934 by George Gershwin and written by DuBose Heyward, the author of the novel Porgy, for the 1935 opera Porgy and Bess.

Holiday would regularly perform the song on her brief stint touring as a big-band vocalist with legendary musician Count Basie. On that tour, amid the rough touring conditions, Holiday did nothing to discount her growing image of diva-like behaviour, and was later fired for being “temperamental and unreliable.”

Basie said about Holiday’s time in the band: ”When she rehearsed with the band, it was really just a matter of getting her tunes like she wanted them, because she knew how she wanted to sound and you couldn’t tell her what to do.”

Strange Fruit’ (1939)

In the 1930s, during her epic run at Barney Josephson’s Cafe Society in Manhattan, New York’s first integrated nightclub, she was introduced to the poem ‘Strange Fruit’, a horrendous depiction of lynching in the Jim Crow south. When her record label denied her request to record the song due to the controversial lyrics, she switched over to the independent label Commodore Records, who would let her record whatever she pleased.

The poem was originally written by a Jewish schoolteacher from the Bronx, Abel Meeropol, and he was there the night Holiday debuted it at Cafe Society. He recalled about the night: “She gave a startling, most dramatic and effective interpretation which could jolt an audience out of its complacency anywhere. This was exactly what I wanted the song to do and why I wrote it.”

Along with the critical praise, calling it “a declaration” and “the beginning of the civil rights movement,” Holiday’s rendition was inducted into the 1978 Grammy Hall of Fame, included in the ‘Songs of the Century’ list of the Recording Industry of America and the National Endowment for the Arts, and even selected for preservation in the National Recording Registry by the Library of Congress.

I’ll Be Seeing You’ (1944)

The original version of ‘I’ll Be Seeing You’ was recorded by Bing Crosby in 1944, instantly becoming a number one. But it’s Holiday’s rendition that she recorded with Eddie Heywood and his Orchestra that is most acclaimed, even today. In February of 2019, Holiday’s cover was the final transmission sent by NASA to the Opportunity rover on Mars when its mission ended. 

Holiday gives the song a moody edge with her evocative vocals and signature inflexions. Along with her reputation as being difficult and moody outside of her discography, it was songs like ‘I’ll Be Seeing You’ that only added to the mystic piling onto her ever-growing career.

Lady Sings The Blues’ (1956)

In late 1956, after releasing her tell-all autobiography of the same title, Holiday came out with Lady Sings The Blues, the album where she finally labelled herself a member of the jazz world, something she was previously reluctant to do. Also during that time, Holiday proved to be more in demand than ever with a book tour, radio interviews, performances, and planning for her return to Carnegie Hall.

Written alongside young jazz pianist Herbie Nichols, the song was recorded in New York City on June 6, 1956, in-studio session number 75. Accompanied by Charlie Shavers on trumpet, Tony Scott on clarinet, Kenny Burrell on guitar, Paul Quinichette on tenor saxophone, Aaron Bell on bass, Wynton Kelly on piano, and Lenny McBrowne on drums, Holiday sang the purely autobiographical song with as much emotion as ever.

‘You’ve Changed’ (1958)

By 1958, Holiday’s health was slowly declining. From years of smoking and drug abuse, her voice was beginning to retain a gruffness, which she used to her advantage in songs like ‘You’ve Changed’. Working with producer Irving Townsend and engineer Fred Plaut, the song appeared on Holiday’s second to last album ever recorded in her lifetime, Lady in Satin.

Although the release was favoured less by her die-hard fans, who preferred her starker jazz combos, Holiday’s return to her contemporary roots was regarded well, making it a full-circle moment to round out Holiday’s career. The original tune was written by Bill Carey with music by Carl Fischer in 1942, but Holiday being Holiday, brought a melancholy edge and a newly husky voice to it, almost signalling an end to an era.