Billie Holiday, born Eleanora Fagan, was a jazz singer from Philadelphia, Pennsylvania. Holiday had a very difficult childhood; her mother Sadie did not maintain steady relationships, and often left home to find work. Young Eleanora dropped out of school after the fifth grade, and was working in a Baltimore brothel when she heard Louis Armstrong and his Hot Five’s recording of “West End Blues”, sparking a lifelong passion for music, and an aspiration to sing, and be known as Billie Holiday. By 1930, she and Sadie had moved to New York City, and when Sadie took a job at a Harlem speakeasy popular with the local jazz musicians, Billie seized the opportunity to sing from table to table for tips. Soon the young Holiday was performing in uptown Manhattan clubs.
Holiday’s big break came when jazz enthusiast John Hammond attended one of her club performances. Twenty-two years old at that time, and hailing from a prominent New York family, Hammond was a correspondent for Melody Maker magazine, a local disk jockey, and a generous benefactor to jazz musicians, offering them the opportunity to record music during the difficult years of the Great Depression. Hammond was enamored with Holiday, and arranged her first recording session with Columbia Records in November, 1933. John Hammond’s role in the development of popular music is hard to overestimate. Not only did he serve as the catalyst for the integration of black and white musicians, he was also the greatest talent scout in pop music history.
Holiday’s first two songs generated modest interest, and earned her a second recording session in 1935, which yielded the hit song “What A Little Moonlight Can Do”. Over the following seven years, Holiday, regularly paired with New York City’s finest jazz musicians, produced a dazzling body of work considered a pinnacle of popular song interpretation.
A Short List of Important Contributors
William “Count” Basie (1904-1984), piano, arranger
Benny Goodman (1909-1986), clarinet
Buck Clayton (1911-1991), trumpet
Freddie Green (1911-1987), guitar
Walter Page (1900-1957), double bass
Jo Jones (1911-1985), drums
John Kirby (1908-1952), string bass
William “Cozy” Cole (1909-1981), drums
Cootie Williams (1911-1985), trumpet
William “Buster” Bailey (1902-1967), clarinet
Johnny Hodges (1906-1970), alto saxophone
Singing With Style
Most music historians consider Billie Holiday the greatest female jazz singer, though she possessed an ordinary instrument in terms of range and volume. She fits nicely within my criteria for singing prowess; I prefer plain sounding voices who subtly augment a song, and shun vocal histrionics. Billie Holiday also advanced the art of jazz singing beyond women like Ethel Waters, Bessie Smith and Sophie Tucker, by mastering the use of the microphone to bring out these subtleties.
“Billie Holiday sang blues only incidentally. But through her phrasing and conception, much that she sang seemed to become blues. She made more than one thousand records — among them about seventy with Teddy Wilson. She made her most beautiful recordings with Wilson and Lester Young. In the intertwining of the lines sung by Holiday and the lines played by Young, the question of which is lead and which is accompaniment, which line is vocal and which instrumental, becomes secondary.
Charm and urbane elegance, suppleness and sophistication are the chief elements in the understatement of Billie Holiday.
When Billie opened her mouth to sing, the truth emerged. Her voice expressed the damage and vulnerability of her soul with an almost masochistic honesty, from desire and lust, to joy and optimism, to doubt, sadness, and pain. Her mouth was like an open wound, she wore her heart on her tongue. And when she sang about loneliness, she drew the listener into her loneliness.
Billie Holiday didn’t just sing sad or happy songs. That’s what women singers in popular music normally do: sing sad and happy songs. In Billie Holiday’s singing, on the other hand, contradictory emotions and feelings exist simultaneously, blending with each other while contradicting each other. Or, as rock singer Bryan Ferry remarked, “Her style sings of hope…her message is despair.”
— Excerpts from “The Jazz Book”, Joachim-Ernst Berendt and Gunther Huesmann
In this 1935 film short featuring the Duke Ellington Orchestra, Holiday makes a brief appearance at the 4:45 mark:
Billie Holiday is an important omission from the original artist countdown list created in August, 2009. Back then I wasn’t hip to Holiday’s contributions, and only had eight songs in the collection. I suspected it was an oversight, and would require some research to rectify. Back in the early nineties I remember marveling at the Rolling Stone Album Guide’s Third Edition, 1992) five star ratings for all nine volumes of Columbia Records’ “The Quintessential Billie Holiday” collection, a level of consistent respect given to the Beatles, Bob Dylan, and perhaps one or two other artists. Over the years I picked up a couple of the Quintessential collections, plus a Commodore Records retrospective to acquire a copy of the protest song “Strange Fruit”. It was only last year that I started the process of creating a representative collection of her music.
My appreciation for her music grows. My interest started with the six to eight-piece jazz bands, and her famous collaborators. I love small band swing jazz, a modernized form of dixieland music; though rhythmically less complex than the Latin and rock syncopation that evolved, the swing rhythm lends itself well to fluid improvisation and clear storytelling. Holiday sings clean and crisp, and adds subtle accents. Her voice does not attempt to dominate or overwhelm. Music analysts often liken Holiday’s style to one of the horn players in the group. Her all-star counterparts do the same, and one gets the sense that the group behaves as a single team, marching forward in step, each voice important to the whole. Classy, restrained and powerful, Billie Holiday interpretations of Golden Age songs created a template for future developments in popular music.
That an abused or neglected person often makes bad decisions about the company they keep is well known. Billie Holiday had a weakness for handsome and abusive men, particularly those who trafficked in heroin. She started using around 1940 or 1941, and struggled with alcoholism and heroin addiction for the rest of her life. She was arrested in 1947 for heroin addiction, and as a result, lost her New York City cabaret card, her primary means of income and support. She was persecuted her whole life one way or another: for being black, for being female, and for being an addict. Her tragic downfall is well documented; through the fifties her health deteriorated, though she continued to perform and record beautifully, albeit with diminishing power. She developed cirrhosis of the liver in 1959, and was arrested for drug possession while on her death bed. Holiday died on July 17th, 1959, just forty-four years old.
Although I devoted more than a hundred hours this past year listening and researching her music, it feels like more investigation is required for the best complement of songs. To close, here’s my favorite Billie Holiday song. In order, the soloists are Benny Morton (trombone), Billie Holiday (vocal), Teddy Wilson (piano), Lester Young (tenor saxophone), and Buck Clayton (trumpet).
When you’re smiling, when you’re smiling,
The whole world smiles with you.
When you’re laughing, oh when you’re laughing,
The sun comes shinin’ through.
But when you’re crying, you bring on the rain,
So stop your sighin’, be happy again.
Keep on smiling, ’cause when you’re smiling,
The whole world smiles with you.
— “When You’re Smiling (The Whole World Smiles With You)” by Larry Shay, Mark Fisher and Joe Goodwin
Billie Holiday Song Notes:
1. Most of the recommended songs can be found on the Columbia Records compilation called Lady Day: The Master Takes and Singles.
2. “Strange Fruit”, “Billie’s Blues” and “On The Sunny Side Of the Street” can be found on Commodore Records compilations.
3. “Lover Man” can be found on Decca Records compilations.
4. “Body And Soul”, “Fine And Mellow”, “What’s New?” and “I Loves You Porgy” can be found on Verve Records compilations.
Billie Holiday Songs:
When You’re Smiling (The Whole World Smiles With You), Billie Holiday ★★★★★
Strange Fruit, Billie Holiday ★★★★
I Must Have That Man, Billie Holiday ★★★
They Can’t Take That Away From Me, Billie Holiday ★★★
The Very Thought of You, Billie Holiday ★★★
Gloomy Sunday, Billie Holiday ★★★
God Bless The Child, Billie Holiday ★★★
These Foolish Things, Teddy Wilson & His Orchestra ★★★
Loveless Love, Benny Carter & His All-Star Orchestra ★★
St. Louis Blues, Benny Carter & His All-Star Orchestra ★★
Body And Soul, Billie Holiday ★★
Body And Soul (Alt), Billie Holiday ★★
Billie’s Blues, Billie Holiday ★★
On The Sunny Side Of The Street, Billie Holiday ★★
Lover Man, Billie Holiday ★★
More Than You Know, Billie Holiday ★★
Long Gone Blues, Billie Holiday ★★
Easy To Love, Billie Holiday ★★
My Last Affair, Billie Holiday ★★
Me Myself And I, Billie Holiday ★★
Mean To Me, Billie Holiday ★★
Easy Living, Billie Holiday ★★
My Man, Billie Holiday ★★
I Cover The Waterfront, Billie Holiday ★★
Trav’lin’ Light, Billie Holiday & Paul Whiteman & His Orchestra ★★
The Way You Look Tonight, Teddy Wilson & His Orchestra ★★
Pennies From Heaven, Teddy Wilson & His Orchestra ★★
I’ll Never Be The Same, Teddy Wilson & His Orchestra ★★
I Loves You, Porgy, Billie Holiday ★
What’s New?, Billie Holiday ★
Fine And Mellow, Billie Holiday ★
I Wished On The Moon, Billie Holiday ★
Miss Brown To You, Billie Holiday ★
I Cried For You, Billie Holiday ★
This Year’s Kisses, Billie Holiday ★
Moanin’ Low, Billie Holiday ★
A Sailboat In The Moonlight, Billie Holiday ★
Sun Showers, Billie Holiday ★
He’s Funny That Way, Billie Holiday ★
You Go To My Head, Billie Holiday ★
I Can’t Get Started, Billie Holiday ★
Ghost Of Yesterday, Billie Holiday ★
Swing! Brother, Swing!, Billie Holiday ★
Can’t Help Lovin’ Dat Man, Billie Holiday ★
Solitude, Billie Holiday ★
Body And Soul, Coleman Hawkins & His Orchestra ★★★
Body And Soul, Louis Armstrong ★★★
Body And Soul, Benny Goodman Trio ★★
Careless Love Blues, Josh White Trio ★
Careless Love, Ray Charles ★★★
Careless Love, Ottilie Patterson & Chris Barber’s Jazz Band ★★
Easy Living, Wardell Gray ★★
Easy Living, Bill Evans ★★
God Bless The Child, Blood, Sweat & Tears ★★★
God Bless The Child, Stanley Turrentine ★★★
I Can’t Get Started, Bunny Berigan ★★
I Can’t Get Started, Lester Young Trio ★★
I Can’t Get Started, Dizzy Gillespie ★
I Cover The Waterfront, The Inkspots ★
I Cried For You (Take 1), Benny Goodman ★★
I Loves You, Porgy, Bill Evans ★★
Lover Man, Dizzy Gillespie & His Orchestra ★★
Lover Man, Sarah Vaughan ★★
Mean To Me, Nat Adderley ★
On The Sunny Side Of The Street, Lionel Hampton ★★
On The Sunny Side Of The Street, Dizzy Gillespie, Sonny Stitt & Sonny Rollins ★
On The Sunny Side Of The Street, Louis Armstrong ★
Pennies From Heaven, Count Basie ★★
Pennies From Heaven, J. J. Johnson ★★
Sailboat In The Moonlight, Ruby Braff ★★
Solitude, Duke Ellington & His Orchestra ★★
St. Louis Blues, Bessie Smith ★★★
St. Louis Blues, W. C. Handy ★
Swing! Brother, Swing! (Live), Count Basie ★★
These Foolish Things, Benny Goodman Sextet ★★★
These Foolish Things, Nat King Cole Trio ★★
They Can’t Take That Away From Me, Ella Fitzgerald ★
They Can’t Take That Away From Me, Frank Sinatra ★★
The Very Thought Of You, Al Bowlly ★★★
The Very Thought Of You, Dodo Marmarosa & Gene Ammons ★
The Way You Look Tonight, Frank Sinatra ★★★★
The Way You Look Tonight, Fred Astaire ★★
When You’re Smiling / The Shiek Of Araby, Louis Prima ★★★
When You’re Smiling (Live), Van Morrison ★★
You Go To My Head, Lee Konitz ★★
You Go To My Head, Louis Armstrong & Oscar Peterson ★