Archives for posts with tag: Billie Holiday


When she started out, Billie Holiday was simply the vocalist for Teddy Wilson’s band. The rise of juke box technology, coinciding with her debut, catapulted her to success for the struggling Brunswick label, ensuring its commercial survival and success, and helping to make Teddy Wilson’s name too. These early numbers (still) deserve a wider audience.

But there are other, less-well-known vocalists who also sang with Wilson then. We know the ‘hits’ we hear now from the first few bars, but if you search YouTube, do you find The Hour of Parting? With the vocalist credited?

Who was Boots Castle, who sang The Hour of Parting with Wilson? A beautiful song written by Spoliansky, who fled Germany for London in 1933.


And who was Jean Eldridge, who sang Moonray with Wilson? Was she related to Roy Eldridge, jazz trumpeter?


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Billie Holiday, cover girl

I’ve mentioned jazz pianist Teddy Wilson in a previous post. What was less clear to me then was how ground-breaking his work with Billie Holiday was. Yes, it sounds gorgeous, as a quick listen will confirm, and not at all like the dark and dramatic Billie of Strange Fruit recorded at the end of 1939. This is light, upbeat, poppy music.

Miss Brown to You

Fox Trot – Vocal Chorus Billie Holiday

That’s one of the first of the tracks to be recorded by Billie and Teddy for Brunswick Records, between 1935 and 1938. Billie Holiday was signed to Brunswick by influential producer John Hammond to record current tunes with Teddy Wilson in the new ‘swing’ style for the growing jukebox trade. They were given free rein to improvise the material. Their first collaboration included “What a Little Moonlight Can Do” and “Miss Brown to You” in 1935. Most of Holiday’s early successes were released under the band name “Teddy Wilson & his Orchestra.” He and Holiday produced 95 recordings together.

What a Little Moonlight Can Do

Not just throw-away hits, these singles were to influence enormously the direction jazz vocals were to take. After the success of “What a Little Moonlight Can Do”, Holiday began recording under her own name  – on the 35-cent Vocalion label – producing a series of extraordinary performances with the swing era’s finest musicians. Hammond said of her, “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.” Listen to “My Last Affair” from 1937 to hear what he means about her phrasing.

(This Is) My Last Affair

Fox Trot – Vocal by Billie Holiday

The Brunswick label was broke and unable to record many jazz tunes. The commercial impact of the Teddy Wilson-Billie Holiday sides from 1935 to 1938 was significant. Because Wilson, Holiday, Lester Young and others came into the studio without arrangements – which cost money – and improvised the material, the records they produced were very cheap.

Holiday was paid a flat fee, not royalties, for her work. Some of the records were successful. The single “I Cried for You” sold 15,000 copies. Hammond said, “15,000 … was a giant hit for Brunswick in those days. I mean a giant hit. Most records that made money sold around three to four thousand.”

In July 1936 Holiday began releasing sides under the band name “Billie Holiday & Her Orchestra.”  The 1936 side “You Let Me Down” is a stand-out, and hints at the darker material to come.

You Let Me Down

By the late 1930s, Billie Holiday had toured with Count Basie and Artie Shaw, had a string of radio and retail hits with Teddy Wilson, and had become an established recording artist. Although she was unable to record in the studio with Count Basie, Holiday included many of his musicians in her recordings with Teddy Wilson. Her songs “What A Little Moonlight Can Do” from 1935 and “Easy Living” from 1937 were being imitated by singers across America, and quickly becoming jazz standards. The road ahead for her was less clear.

Easy Living

Billie Holiday opens at the Apollo Theatre in Harlem with Basie in 1937

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