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The Real Billie Holiday, Part One – 1930s

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Early Recordings and Original Songs

Starting in 1933 Billie made her first records in sessions with Benny Goodman and Teddy Wilson.  But by 1936-37 she was recording under her own name with fine musicians mostly of her own choice.

Among her favorites for those session were trumpeter Buck Clayton and tenor saxophonist Lester Young.  She’s with them in the set below on “Back in Your Own Back Yard” and “This Year’s Kisses” — which was the first of 50 tracks she and Lester recorded during the late-1930s.

A popular and critical success, her discs sold well.  Listeners responded to the special lilt she brought to songs that might otherwise have been easily forgotten.

What a Little Moonlight Can Do

Them There Eyes

Back in Your Own Back Yard

This Years Kisses

Lester Young, “Prez.”

With Saxophonist Lester Young

There has been much comment about the remarkable musical synergy between Holiday and saxophonist Lester Young (1909-1959).  They formed a brilliant intuitive partnership fusing singer and accompanist into a single melodic and tonal instrument.

A quirk of Lester’s odd speech patterns was addressing his acquaintances as “Lady.”  The sobriquet “Lady Day” stuck to Holiday, who returned the compliment:

“When it came to a name for Lester Young, I always felt he was the greatest.   The greatest man around then was Franklin D. Roosevelt and he was the President.  So I started calling Lester the President.  It got shortened to ‘Prez,’ but it still means what it was meant to mean — the top man in this country.”

8A) Gardenia B


From Popular Singer to Songwriting Diva

Through the 1930s Billie recorded mainly popular ballads and Tin Pan Alley tunes.  Yet her improvisations were equivalent to Louis Armstrong, Bessie Smith or Frank Sinatra in the way she radically streamlined, revised and improved the melodic and rhythmic elements of song.

Holiday was writer or co-composer of several very good songs, including some of her biggest hits like “Fine and Mellow” (1937), “God Bless the Child” (1941) and “Lady Sings the Blues” (1956).

Fine and Mellow

God Bless the Child

Lady Sings the Blues

Holiday called the blue-eyed, well-dressed trumpeter Buck Clayton, “the prettiest cat I ever saw.

“Cat Eyes” Buck Clayton

During her short time touring with the Count Basie Orchestra, Holiday became very close to trumpeter Buck Clayton (1911-1991), previously profiled in this column.  Buck, Billie and Lester were good buddies.  She and Clayton certainly had a musical love affair.  His impeccable accompaniment in her best sessions was sensitive and intimate.  Buck and Prez remained her most favored partners and accompanists through the 1930s.

Clayton shared fond recollections of working with her in his 1986 memoir, Buck Clayton’s Jazz World:

“Such pleasure I had backing up Billie’s songs to her vocals.  When she would record I would watch her mouth and when I saw she was going to take a breath or something I knew it was time for me to play between her expressions.  It’s what we call ‘filling up the windows’.”

Billie Pt 1 – 1930s – Podcast clip C.mp3

10A) Cigarette 1954


Diva Rising

By the late-1930s Billie Holiday’s record sales were high and her artistry blooming.  She was turning from popular song toward dark ballads, blues and her striking originals.

As the 1940s dawned she had become a smoldering artiste, a Diva prepared to step into the limelight and fully express herself, performing on a broader canvas as depicted in part two.

11A) Young and Healthy


Sources and thanks.  Billie was quoted from her autobiographical memoir, Lady Sings the Blues, (Billie Holiday with William Dufty, Doubleday, 1956) read by Kitt Weagant.  Buck Clayton was quoted from Buck Clayton’s Jazz World (Oxford University Press, 1986) read by Joe Hughes.  The words of Artie Shaw were read by Peter Coyote.  Thanks to Hal Smith for assistance.


7 Responses to The Real Billie Holiday, Part One – 1930s

  1. SAVVAS says:

    Thank you! So nice article !

  2. You can explore Billie’s life, music and associates here:

    The official home of Billie Holiday

    Billie Holiday on Jazz Rhythm

    Buck Clayton on Jazz Rhythm

    Lester Young on Jazz Rhythm

  3. Bill Opdyke says:


  4. Larry G says:

    Can wait for the next two decades. Keep it coming.

  5. Jack Bybee says:

    Dave another wonderful article.

    Jack Bybee

  6. Thank you, gentlemen and stay tuned. Everybody loves Billie. Dave R

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