Billie Holiday: ‘Lady Sings the Blues, She Tells Her Side, Nothing to Hide’

Often in jazz, when identifying the soaring range or virtuosity or power of a vocalist, these gifts are accepted as a skill set that is necessary to impart the depth and complication of song material. Through 1930s to her death in 1959, Billie Holiday, singing within a vocal range of barely an octave, conveyed an arc of emotions drawing on her own personal experiences with life’s hardships. Holiday often said she was trying to sing like a horn, but her own vocal statement, with a muted timbre, was instantly recognizable to both audiences of her era and today. She is regarded by jazz critics as a seminal counterpoint to the established towering figures of female jazz vocalists: Ella Fitzgerald and Sarah Vaughn. But within her limited range, Holiday would change the art of jazz singing forever.


During the most active period of song production of the Tin Pan Alley era (approximately 1895 – 1930), singers were rarely allowed to have individual vocal expression, with the possible exceptions of Bessie Smith, Louis Armstrong, and Ma Rainey. Holiday was listening to both Bessie Smith and Louis Armstrong, searching for an outlet for her independent voice. Recording under the Tin Pan Alley system in the early ‘30s, there was a formula template for singers, and improvisation was simply not allowed. In addition, Holiday, along with other contemporary musicians, were not given the rights to their recordings – once sold to the publisher – just a one-time payment to the artist with no reccurring royalties. For part of her early career, Holiday would rely on the income from sales of popular ballads through this system.


In the mid-to-late ‘30s, Armstrong was trailblazing with floating vocal notes, introducing “scat” singing. Lady Day, (her singing persona nickname, courtesy of Lester Young), though initially a blues singer, was also starting to reshape her phrasing of jazz standards and changing the arrangements of many songs into her own version, copying no one. In her own words, “I feel like I’m playing a horn. I try to improvise like Lester Young, like Louis Armstrong, or someone else I admire. What comes out is what I feel. I hate straight singing, have to change a tune to my own way of doing it. That’s all I know.”

As her personal life was revealed more fully in her unflinching memoir, Lady Sings the Blues (1952), the stark retelling of her traumatic life, including prostitution, physical and sexual abuses, and drug addiction, Holiday’s perseverance was echoed in her emotional delivery and phrasing. Her versions of a select number of songs have become imbedded in Holiday’s repertoire. Lover Man, Solitude, Don’t Explain, Strange Fruit, and her own composition, God Bless the Child are all uniquely and stylistically tied to her songbook. AllMusic jazz critic John Bush reflects on Holiday’s interpretive impact: “Holiday’s best performances (of these songs) remain among the most sensitive and accomplished vocal performances ever recorded.”

Her recording of Strange Fruit in 1939 was groundbreaking. It was a direct and historical statement about racism made by a black jazz musician, in this case a woman. Written by a Jewish poet about the lynching of African-Americans in the South, her performance of this song at Café’ Society, New York City’s only truly integrated nightclub, socially and politically changed the history of American music. Holiday remembered, in her memoir, this first performance as related in a New York Times article specifically about the impact of Strange Fruit and Holiday’s brave, defiant stance:

“Holiday was to recall, even in this café, she was afraid to sing this new song, a song that tackled racial hatred head-on at a time when protest music was all but unknown and regretted it – at least momentarily– when she first ended the song. ‘There wasn’t even a patter of applause when I finished,’ she later wrote in her autobiography. “Then a lone person began to clap nervously. Then suddenly everybody was clapping.” Covered in the ‘40s and ‘50s by many peer jazz vocalists and reinterpreted by contemporary artists today, the late jazz writer Leonard Feather called Strange Fruit “the first unmuted cry against racism.”

Outside of her arrangement from the poem that became Strange Fruit, later in her career Holiday would write and co-compose some of her signature songs, including Fine and Mellow (1937), God Bless the Child (1941) and Lady Sings the Blues (1956). These also became some of her biggest hits.

During the ‘30s, Holiday was a featured singer in several big band orchestras including Count Basie (along with a particular musical attachment with trumpeter Buck Clayton), Artie Shaw, Fletcher Henderson and particularly the virtuoso swing pianist Teddy Wilson and his orchestra. This was the period of dance floor contests and Big Band playoffs (a competition of performances between orchestras, as measured by the volume of applause).

As a turning point for her artistry of vocal expression, it was with Teddy Wilson that Holiday first began experimenting with phrasing and improvising, which had been encouraged by the period jazz impresario and producer John Hammond. Forced to record a lot of Tin Pan Alley standards, Holiday broke from the traditional singing formula. Some period examples include What a Little Moonlight Can Do, Miss Brown to You, Easy Living, and Mean to Me. What A Little Moonlight Can Do was later deemed to be her “claim to fame” during the period together with Wilson.

Holiday’s intersection and forthcoming musical relationship with legendary tenor saxophonist Lester Young occurred during this same interchange of musicians, under Hammond’s production. There was clearly a special chemistry between the musicians, also felt and expressed by other peer jazz musicians. Too, they shared similar emotional pain, with both of them fighting their inner demons with drugs and alcohol addiction. Young explained the rapport in his own words, “I think you can hear that on some of the old records, you know. Some time I’d sit down and listen to ’em myself, and it sounded like two of the same voices…or the same mind, or something like that.”). During this intermittent but lasting musical relationship Billie Holiday and Lester Young recorded a series of memorable sides together including He’s Funny That Way, Travlin’ All Alone, and Easy Living.

By the end of the 1930s, Holiday’s record sales were in high demand as her artistry blossomed. As stated by jazz radio broadcaster and critic David Radlauer, in his article The Real Billie Holiday, Part 1, 1930s, “She was turning from Tin Pan Alley toward dark ballads, Blues and her own striking originals.  Stepping into the limelight and onto the world stage she was an artiste prepared to express herself on a broader canvas.”

Several key songs Holiday recorded in the ‘40s charted on Billboard, including Lover Man (number 16 pop, number 5 R&B). With recording contracts first with Columbia and then Decca, she would compose, record, and perform some of her most enduring songs, including Strange Fruit (1939), God Bless the Child (1941), and Lover Man (1944). Holiday’s covers of Bessie Smith’s Tain’t Nobody’s Business If I Do, Them There Eyes, and Crazy He Calls Me would also become some of the best loved songs of her career. (


At the height of her artistry and recording contracts and demand for performances, Holiday had succumbed to a variety of drug addictions and alcohol dependency, climaxing with a narcotics arrest and conviction, receiving an 8-month jail sentence in 1947. After her release, with her drug conviction keeping her from a cabaret card required for performing in New York City clubs, she was able to return to recording, initially with jazz entrepreneur Norman Granz, and then Verve Records. These recordings also included sessions with stellar musicians – Oscar Peterson, Harry “Sweets” Edison, and Charlie Shavers.

Holiday would tour Europe in ’54, to great reviews, audience reception, and international acclaim. Back in the U.S., she had also reunited with jazz tenor Ben Webster and returned to a more intimate nightclub environment with this series of recordings. Sadly, due to her loss of a cabaret card, US audiences would miss live performances, where Holiday always translated her emotion on stage. Webster is also credited with equally matching her weakened tone at this stage in her life. “The listener catches the feeling that all the musicians are devoted to Holiday…No one seeks exposure at the expense of the others; all function as a homogeneous group…Ben is particularly considerate in his obligattos, never getting in the way, but always keeping his velvet tone under her voice and thus helping carry her forth. He is equally considerate in his solos, never using growl in fast tempi, probably feeling it would be overpowering in comparison to Holiday’s fragile voice…”

She would give her final Carnegie Hall performance on November 10, 1956, and though frail and unable to provide the audience with a peak performance, Holiday still delivered a personal innermost statement in voice. The late jazz critic, author, and columnist Nat Hentoff was there: “The audience was hers from before she sang, greeting her and saying goodbye with heavy, loving applause. And at one time, the musicians too applauded. It was a night when Billie was on top, undeniably the best and most honest jazz singer alive.”

As her health continued to deteriorate with further addiction to heroin and continued heavy drinking, her brittle voice, weakened physical stamina, and ongoing emotional strain of her personal life, all collectively led to a downward spiral in the last years of her life. Lady in Satin, released in ’58, would be her last record label recording. As reviewed by jazz critic Michael Brooks, it was a parting farewell, with orchestra strings backing up a tired and failing voice, “A heartbreaking beauty…this 1958 album feels as if a group of family and friends are gathered around a loved one and saying their last goodbyes.” Holiday died a year later.

Holiday would be brought to life in the acclaimed 1972 biographical film Lady Sings the Blues, with a remarkable performance by Diana Ross, who would win a Golden Globe award as well as earning a Best Actress Academy Award nomination. The biopic would become a vehicle to tell her life story to a wider and younger viewer and listening audience.

In 2013, to overwhelming positive reviews, contemporary jazz vocalist Dee Dee Bridgewater would portray Holiday and perform her songbook in the off-Broadway musical Lady Day.

There are numerous biographies, documentaries and box sets of recordings available, including the exceptional period recordings during the Columbia and Decca years.

Her impact on current jazz singers remains significant and wide-ranging, as she was unique in exposing her pain and emotion in her life, delivered without disguise or pretense in her voice. Both contemporary renowned jazz vocalists Cécile McLorin Salvant and Cassandra Wilson follow her influence and have given tribute performances, headlining Holiday’s songs. Current baritone singer Jose James, who made a record inspired by Holiday, Yesterday I Had the Blues (2015), summed up his vocal learning in phrasing and harmony that he credits Holiday for, particularly from one of her biographical compositions I Cried for You:

“At that point she couldn’t lean on anything except her spirit, so to me, that album more than any other proves how committed she was to really expressing the sort of maze of the human heart. She was really a professor. And she was trying to figure it out for herself too. Yeah, she’s super-real. She’s somebody who I need to study with for the rest of my life. Not just as a singer, but as a person.”

Having led her life on stage and in the public eye, without hiding her soul and muse for her voicings, in the first three stanzas from her biographical musical ode, Lady Sings the Blues, Holiday could easily be singing about her life story:


Lady sing the blues,
She’s got them bad,
She feels so sad.

And wants the world to know,
Just what her blues are all about,


Lady sings the blues,
She tells her side,
Nothing to hide