‘Maybe I Can Sing’: Remembering the Voice of Anita O’Day


When we hear mention of the great female vocals of jazz, most will tend to think of Ella Fitzgerald and the great Lady Bird herself. Less frequently, we think of Lena Horne and Sarah Vaughn. The true aficionado will have their own favorite great lady of jazz come to mind. One of our favorites is the oft forgotten Anita O’Day.

Maybe I can sing

Although a phenomenal documentary, Anita O’Day: The Life of a Jazz Singer (2007), was released just a year after her passing, many portions of her personal and professional opus remain unsung.

O’Day possessed, undeniably, one of the most distinctive voices in any genre, ever. She owed the uniqueness of her voice and almost recitation-like singing style to a childhood tonsillectomy gone terribly wrong. The botched procedure left her voice handicapped and, quite literally, lacking the physical capability to hold notes or sing vibrato. But the persistent young O’Day, through years of practice and hard work, turned this into an advantage and conquered colleagues and audiences all the same.

In the film, a young O’Day steps onto the stage of the Newport Jazz Festival in a barely there cocktail dress and her infamous glass slippers, proceeding to mesmerize the audience with the effort a child makes to draw a smile from its mother.

Anita O’Day at Newport Jazz Festival 1958. Still from Jazz on a Summer’s Day by Bert Stern.

In many ways, O’Day’s life and career were the essence of jazz and her time. Born in Kansas and raised in Chicago at the height of the Great Depression, O’Day was the perfect blend of the lowbrow elegance that so many jazz singers and musicians aspired to.

Growing up in a blue collar family, it was O’Day’s mother that set aside time during the week to teach her to play the piano and carry a tune. By age 14, and already too mature and feisty for her own good, O’Day signed up for a dance marathon, immediately winning second place on her first try, then joining the plenty older dancers on a tour. Having always aspired to be a singer, she soon began singing on these tours, for tips.

Despite the occasional dance marathon touring, O’Day managed to finish high school and was more than ready to leave home. She soon joined a Chicago dance act, the Six Young Ladies, but quit on her second night with the group, after barely being able to escape persistent men after their performance at the Celebrity Club.

In another documentary, she is quoted as saying around that time, “I don’t know. Maybe I can sing.” And soon she was doing just that, taking any gig she could get in Chicago’s night clubs.

An invitation from Dick Buckley, a danceathon buddy, came soon after to join his show at the Planet Mars and O’Day had steady work as a singer. She practiced daily, listening daily to the likes of Mildred Bailey and Billie Holiday.

Her first success came in 1930, with Let Me Off Uptown, recorded while she was with influential Chicago drummer Gene Krupa’s band. Among her next successful successful song is a reminder of her singing roots, And Her Tears Flowed Like Wine, which was picked up by the director of The Big Sleep, in which Lauren Bacall’s character sings the tune, popularizing it almost immediately.

Unfortunately, O’Day’s troubles grew with her career. Though she wants to sing essential jazz pieces, she is coaxed and pressured by producers, managers, and fellow musicians to sing more popular songs. By this time, she has also picked up a drug addiction and is out all night and sleeping all day.

In 1955, despite difficulties, she released her debut album, with both jazz and more poppy tunes, titled simply Anita. In the next decade, O’Day recorded and released another twenty or so albums, each one jazzier than the last. Within time, these get here on the headliner lists of the world’s most prestigious jazz festivals and concerts throughout North America, Europe and as far as Japan, by the mid 1960s. O’Day was on a roll.

Anita O’Day, photo by Daniel Shen Taipei, Taiwan [CC BY-SA 2.0], via Wikimedia Commons

High as a kite

O’Day kicked her drug habit in 1967, but not before experiencing an overdose and clinical death. Speaking of her drug addiction later, she admitted to either being “high as a kite” or simply not remembering many of her performances. The addiction had become an intricate part of her music and voice.

After a period of recovery, mostly in Hawaii, O’Day returned to the stage and regained her popularity. Her 1970 performance at the Berlin Jazz Festival remains one for the books and she continued to perform worldwide into her 70s, staring her own record label in the meantime.

Her voice had been changed, however, and this never went unnoticed. Many say her voice lacked the power it once had, often chalking it up to the influence of heroin, O’Day’s poison of choice. Others simply thought her time had passed. Whatever the opinions may be, O’Day was and remains a timeless influence in jazz and singing overall.

Months before her death in 2006, O’Day released her final album, titles as simplistically as her debut album – Indestructible!. And perhaps Anita O’Day wasn’t indestructible – but that voice sure sounds like it is.

O’Day’s two outings with Billy May are Viva Virtuoso favorites. Decadently polished, like Strawberries Arnaud with a Pappy Van Winkle’s chaser, so to speak.

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