Lester & Billie: BFFS

I have written a LOT about Lester Young. Seriously – if you love testing your patience and want to give yourself a particularly gruelling challenge, go check out my 85 page wanderings through his fascinating life.

For anyone who -shockingly – doesn’t want to invest the time, here’s a brief synopsis:

Born just outside of New Orleans, Lester Young earned his chops touring with the family band before migrating north to escape the ill treatment he suffered in the Jim Crow South. He established himself as an endlessly creative and refined player in the best swing bands of the 1930’s like Fletcher Henderson’s and Count Basie’s. The selection below shows Lester at the peak of his swing career. His solo compositions are very much outside the definitive style of the day and reflect his quirky personality.

Lester Young was an influential jazz saxophonist revered in musical circles as not only the inventor of cool jazz, but also as the inventor of the slang term ‘cool’ itself.Though he was generally respected, he was seen as firmly outside of societal norms for several qualities: his distinctive sartorial style (his signature “pork pie”hat; his cryptic, idiosyncratic slang vocabulary, fabled to have popularized the terms ‘cool,’ hip,’ and even ‘motherfucker’; and even the tone of his saxophone playing.


But his big non-conformity, the one that fed into all the other elements of his personality and drew sidelong glances for his unique traits, was gender. Lester was followed his whole life by a rumour that he was queer – a rumour that most of his biographers agree started with his close platonic friendship with Billie Holiday.

Now before we go any further, let me just say that I’m not trying to confirm or deny that Lester Young was queer. For one thing, it doesn’t matter, and for another, it is not for me to decide. Sherrie Tucker wrote a great piece that grounded me as I approached this very sensitive topic. In short: Lester Young was queer inasmuch as he existed outside the “straight” lines of societal expectations for his race and gender during the climate in which he existed.

Whoops, sliding back into academic mode there…let’s return to the BFFs.

Billie Holiday’s and Lester Young’s friendship was a beautiful thing in both their lives. Both had to navigate very limited personas placed on them by the media. They understood each others’ oppression, and they understood each other’s musical voices. They were such close friends that at one point Lester moved in with Billie and her mother.

And that was where the rumours started. Billie Holiday was considered an exotic beauty, and due to a very publicized tragic life story that sensationalized her past as a child prostitute and her drug use, had a bit of a fallen woman vibe about her. Basically, Lester’s wrong move here was that he didn’t ever try to have sex with her. It was mystifying to outsiders of their relationship that he could be interested in her as a friend and respect her as a musician. Many of his biographers conclude that his failure to make her his lover could only be explained by queerness.

I like to conclude that they were just two people who understood each other personally and artistically. In a word – friends.

The following clip is one I had seen before but not truly appreciated until I understood the significance of Billie & Lester’s friendship.

It is an all-star recording of Fine and Mellow, one of Billie Holiday’s original blues compositions. Billie and Lester were both very close to the end of their lives at this point, both in very bad health, and were coming together for the first time after a falling out and a long stretch absence.

Coleman Hawkins takes the first solo. A very popular player with a bigger, bolder, faster style, he had always been positioned as Lester’s rival in jazz press.

But when Lester’s solo lazily slides in in a few short bars later, the camera catches Billie’s face in a moment that brings all of this background together. At 1:41 in the video, watch as Billie listens raptly and seems to see what Lester is doing with his improvisation. That look says much more than I could possibly explain here. So do yourself a favour, and watch!








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