An Affair To Remember: Lady Day and The Prez

History has a way of creating pairs. Lovers and enemies, comrades and counterparts. God and the Devil, Romeo and Juliet, ketchup and mustard. We pair our socks, our parents and the salt and pepper shakers. Without detracting from the greatness of the above examples, I would also ask you to consider a lesser known pairing: Billie Holiday and saxophonist Lester Young

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To any jazz enthusiast, this is a no brainer, but to the rest of us musical laymen, a pause and plausible explanation is expected. In short, they were the greats on their principal instruments: Billie is one of the legendary vocalists and jazz stylists, while Lester became the king of Cool Jazz and all that it encompassed. Each had their own unique style, fought for on the road and in the dingy clubs. They spent years travelling with different band leaders, having nightly engagements in clubs worldwide, honing their own musical interpretation. Billie had no training, relying on innate ability, a willing ear and her own inner rhythm. Lester was proficient on multiple instruments, having learned from his father at a young age. He cut his teeth playing in his family’s traveling vaudeville band. They met by chance in the 1930s, as members of Count Basie’s band. In the early 40s, Lester was brought into some of Billie’s recording sessions, and at was no less than a musical marriage.

It’s easy to assume they were more than a musical pair, from the sound of their interplay on recordings. Unlike anyone else, they could read each other’s next move. Her vocal lines melted into his solos, which in turn became the warm underbelly of her melody. They never fought each other, but relinquished willingly. Their own styles were in tune with each other; they both hit behind the beat, nothing punchy or fancy, giving breadth to each phrase.

In “The Man I Love”, Billie’s vocal line gives way to Les’ sax, which plays up the melody without over-playing:


Here’s a radio clip from 1958. Listen to Prez talk about Lady Day:


In “A Sailboat In The Moonlight”, you can hear Lester beneath Billie’s vocal line. He’s buoying her up, never playing over, but supporting every note. It’s two voices in a duet. Later in the song, he comes in with a mellow solo, taking her melody and putting his own spin on it.

The extent of their friendship is clouded at best, and really, it’s irrelevant. Lady Day was always adamant about the fact that they were just friends. Whether or not they were lovers doesn’t matter, because we’ll never know. What we have are the marks they left on wax. Through the music we can hear their friendship; they connected on a cerebral and emotional level that translated in song. Taking similar paths down the road of excess and abuse, their early deaths came less than six months apart. Prez died unceremoniously in a NYC hotel room from alcohol related complications. Lady Day met her end in a hospital room, having been placed under arrest a final time for narcotics charges. Their nicknames are as well-known as their real ones, both being created by the other.

Her ebb fit perfectly into his flow. You can’t ask for a more seamless partnership, in music or marriage. They lost touch for years, but joined up one last time in 1957, for a filming of CBS’ The Sound Of Jazz. There, with a who’s who of other jazz greats, Billie and Lester gave a heart stopping rendition of “Fine and Mellow”. Though the years had taken their toll, both rose to the challenge and worked their magic:


Here’s to jazz’ hippest, coolest couple.

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2 Responses to An Affair To Remember: Lady Day and The Prez

  1. I love this stuff! I feel like I learned a lot, too.

    P.S. Your show at Springwater was great! You guys should make that a Sunday night thing. And now I expect a Sax at your next show.

  2. Nicci says:

    I cannot imagine a more perfect pairing in any musical genre. Sadly, a lot of people focus on the tragedy of Billie Holiday’s life but she could evoke so many emotions. The term ‘genius’ is bandied around so freely thesedays but Prez and Lady Day are worthy of the title.

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