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Billie Holiday was nobody's fool — but that didn't stop her from singing about it

Billie Holiday
Billie Holiday during the sessions for 'Lady in Satin,' 1958.

April Fools’ Day has been celebrated around the world for centuries, yet its exact origins remain a mystery. So today we revisit the mystery, mastery, and sonic quality of an appropriate anthem: Billie Holiday’s version of “I’m a Fool to Want You.” A song created for anyone fooling through the depths of love and desire.

“I’m a Fool to Want You” is the opening ballad on Lady in Satin, the penultimate album recorded by Holiday and the final work released in her lifetime.

Seven years before she entered the studio to record this iconic rendition, Frank Sinatra, Jack Wolf, and Joel Herron composed the lyrics. This writing credit was unique for Sinatra, who like many of his contemporaries relied heavily on professional songwriters.

What may have moved Sinatra to the poetics of songwriting was his love entanglements at the time. He was ending a marriage with his first wife Nancy Barbato, and seeking out new love in the arms of Ava Gardner. While we will never know who exactly the fool is in “I’m a Fool to Love You,” it is clear that the “foolishness” that comes with heartbreak and falling in love was weighing heavily on Sinatra’s heart at the time. He crafted a song that exposed the vulnerabilities of love and gave audiences permission to be lovers exasperated by the foolery of love.

In 1958, at the time of the Lady in Satin recording, Billie Holiday was 43, and had certainly experienced the ins and outs of love. The sonic quality of her voice, combined with her life experiences as a Black woman in the music industry, gave rise to a new version of the song quite different from its previous iteration with Frank Sinatra and the Ray Charles Singers on March 27, 1951.

As the song opens, Holiday takes her time with the initial repetition. She sings:

I'm a fool to want you
I'm a fool to want you
To want a love that can't be true
A love that's there for others too
I'm a fool to hold you
Such a fool to hold you
To seek a kiss not mine alone
To share a kiss the Devil has known

Her vocal intonation is full of experience, as if each syllable is conjuring a memory of loves that can never be returned, or true. She offers a performance that is potent and unbridled as she continues:

Time and time again I said I'd leave you
Time and time again I went away
But then would come the time when I would need you
And once again these words I'll have to say

Take me back, I love you
Pity me, I need you
I know it's wrong, it must be wrong
But right or wrong I can't get along
Without you

There are moments when Holiday seems to be singing to the audience, and moments when she sings to herself expressing surprise at her own longing to be desired by the you in the lyrics. She moves this song from pop to jazz to blues, making the entire personal experience of her life inseparable from the lyrics written. In 1958, a new version of this song was born and gave listeners permission to embrace the foolish ways of love.

Jamara Wakefield is an arts and culture writer and creator currently living in Newark.