Of all the singers of the big band era, four stand out from the crowd. Though each developed their own vocal style, all four (and thousands of lesser lights) owe a debt of gratitude to the vocal recordings of Louis Armstrong.


Although they broke into the music business in the jazz field, due to the mainstreaming of their vocal styles and repertoire, Bing Crosby and his successor, Frank Sinatra are more often recognized as pop singers than jazz singers.
The two other voices which made an impact on music in the big band era were Billie Holiday and Ella Fitzgerald. Perhaps unlike any other singers of the era, they crafted melodies in the style of a jazz instrumental soloist. Because of this, they could be viewed as coming as close to the Armstrong standard as any “mere” singer of the era. In fact, both Holiday and Fitzgerald recorded duets with Armstrong that displayed their technical skill and artistic phrasing.
One cannot understand the artistry of Billie Holiday without looking at the incredible heartaches that were part of the fabric of her life. There were times, in fact, when the newspaper stories of her strife-torn life were the total substance of the public image of Holiday.
Certainly there was much to sensationalize. Stories of early abandonment by both mother and father, emotional and physical abuse by relatives, childhood prostitution, drug addiction, prison time, spousal abuse, bankruptcy, and eventually death by narcotic overdose were all part of the catalog of sorrow that was Holiday’s life. Even if the severity of the childhood stories were embellished, the heartbreak in the latter part of her life is easily verified.

At 13, Billie left Baltimore for New York City to join her mother. After being arrested for prostitution and spending time in prison, Holiday was able to get a job as a dancer in a Brooklyn night club. The night before she and her mother were to be evicted from their apartment, Billie was able to earn a couple of dollars by taking the mic and singing a few songs. The sound of a 15 year old girl singing “Trav’lin’ All Alone” so moved the audience that the club owner hired her to provide regular performances. Within two years, Billie had moved from small clubs in Brooklyn to the more prestigious ones of Harlem.
It was then that Benny Goodman’s agent discovered her and signed her to three recording sessions with the Goodman band. This exposure opened the doors for additional studio work with Lester Young, Teddy Wilson, and the big bands of Count Basie and Artie Shaw. In 1938, Holiday toured with the Artie Shaw Band, becoming the first black vocalist to travel with an all white dance band. Although it was a milestone in racial/musical history, it was not without its “Holiday” poignancy. While in the South, the band was allowed to eat in the diners, but Billie ate her meals by herself on the bus. On another occasion, while performing as a headliner at a hotel, she was forced to take the freight elevator to her room after the performance; ironically, the hotel was named the Abraham Lincoln.
Of all the heartache songs recorded by “Lady Day” as Holiday was nicknamed, perhaps none was more moving or more distressing than “Strange Fruit,” performed first in 1939 at the multiracial Café Society in Greenwich Village, NYC. Abel Meeropol, a Jewish poet, wrote the lyrics after reading about the lynching of blacks in the South.
Southern trees bear a strange fruit,
Blood on the leaves and blood at the root,
Black body swinging in the Southern breeze,
Strange fruit hanging from the poplar trees.
How painfully fitting that a song written by a Jewish poet in America became an anthem of protest against unspeakable atrocities during an era when both black and white Americans were fighting to free Jews from their own hellish conditions in Eastern Europe.
The manager at Café Society, where Lady Day would frequently perform, made her do the song as her final number of the night. He carefully set up the moment so that the impact of the song and Holiday’s interpretation would be maximized.
“The room was completely blacked out, service stopped–at the bar, everywhere. The waiters were not permitted to take a glass to the table, or even take an order. So everything stopped–and everything was dark, except for a little pin spot on her face. That was it. When she sang “Strange Fruit,” she never moved. Her hands went down. She didn’t even touch the mike. With the little light on her face. The tears never interfered with her voice, but the tears would come and knock everybody in that house out.”
The attention she was given for her recording of “Strange Fruit” opened more doors to perform and record in the 1940s. It was during this time that Holiday did some of her finest work. Although some of her songs were of a light, pop nature, it was the songs that seemed to stem from personal experience which received critical acclaim. “Gloomy Sunday,” (1941) a suicide song; “Lover Man,” (1944) about an abusive relationship; and “God Bless the Child,” a song she co-authored which perhaps most closely reflected the heartbreak of her life.
But by the early 1950s, Holiday’s personal life was but a collection of misfortunes. Her drug addiction led to arrest and prison time; her life savings were stolen and embezzled by those closest to her; and deep depression set in resulting in further isolation and lost singing engagements.
Before her death in 1959, supposedly of a narcotics overdose, Lady Day co-authored Lady Sings the Blues, an autobiography, which, although it contains grossly inaccurate information of her early life, certainly conveys the intense ache in her life that gave emotional substance to her work. Though a movie version of the autobiography, starring Diana Ross, was made in 1972, the same inaccuracies and fictionalizations remained.
Regardless, Billie Holiday remains as one of the most intense and emotional vocal artists of the big band era. Like Satchmo, she had the incredible ability to allow the feeling of the song to guide her in crafting the melody, which became, at times, completely detached from the ground beat, and then stretched or condensed to suit the moment.
Billie Holiday with Louis Armstrong, 1947 – “The Blues are Brewin'”