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Amy Winehouse and Billie Holiday: The dual fate of two jazz greats


When Amy Winehouse released her debut album, Frank, in 2003, music writers immediately drew parallels between the then 19-year-old singer-songwriter and the jazz icon Billie Holiday. Although the pair came from very different backgrounds, it seemed as if Winehouse had somehow absorbed the spirit of Holiday. Her voice seemed to ripple with the same longing, the same heartache, and the same subtle fire. But as the Frank singer’s career took off and the media latched on to her, it became apparent that Winehouse and Holiday had more in common than their soulful vocals. In the eyes of the media, their fate seemed aligned.

Amy Winehouse was born in 1983 and fell in love with jazz music from an early age. As a young teenager, she was a member of the National Youth Jazz Orchestra and honed her voice by listening to the likes of Frank Sinatra and Dinah Washington. By 2002, she was already signed to EMI and went about recording her debut soon after. Frank was released to critical success in 2003 and garnered Winehouse a Mercury Prize nomination for the song ‘Stronger Than Me’. But it would be the singer’s follow-up, Back To Black, that would cement her as one of the UK’s biggest stars. At the 2007 Brit Awards, the album was nominated for Album of the Year, and Winehouse received the award for Best British Female Solo Artist. Later that same year, Winehouse also became the first female artist to win five Grammy Awards.

But behind all this, as the media made abundantly clear, Winehouse was struggling with severe alcohol and drug addiction. Part of the reason Winehouse was so readily compared to Holiday was because of this strange parallel. Winehouse’s addiction, as explored in the biopic Amy, was tied to her relationship with her partner Blake Fielder, who was also struggling with drug addiction and has since been accused of manipulating Winehouse during her weaker moments, with some describing him as an enabler.

For years, the Camden singer became the laughing stock of gossip magazines, her antics, court hearings and complex relationships with rehabilitation therapy, all making the front pages time and time again with the jeering public faintly heard with every turn of the page. Unsurprisingly, the scrutiny of the tabloid press did nothing but push Winehouse further and further into addiction. And because of the parallels between Winehouse’s addiction and that of Billie Holiday, the public managed to convince itself that Winehouse’s complex personal life was all part of the theatre of her act. As if she was somehow trying to replicate the life of one of her idols.

Billie Holiday had a famously difficult life. Her childhood was one defined by parental absence, poverty, and eviction. As she grew into adulthood, however, her career blossomed. With songs like ‘Strange Fruit’ and ‘God Bless This Child’, she established herself as one of the most talented jazz singers in America. But after she was charged with drug possession in 1947, Holiday was pursued by the outwardly racist federal investigator Harry Anslinger. With the help of the media, Anslinger succeeded in destroying Holiday’s reputation. After being arrested again on January 22, 1949, the jazz singer began using hard drugs. As her prized voice gave out under the strain of her alcohol and drug abuse, her record sales slumped, and Anslinger’s apparent mission seemed complete.

Like Holiday, Winehouse’s career was shaped by the perception the public had of her. Both stars were reprimanded and flogged in the public sphere for their addictions. And this derision, in both cases, only reinforced either stars’ desire to escape into the soft shell of substance abuse. But, for the media, it was all part of the romance.

‘How poetic?’, they must have thought, for two lives to be so inextricably linked that they suffer the same fate. Although Winehouse attempted to separate herself from the shadow of Billie Holiday, she never quite succeeded. She tried to make her disdain known when she said “fuck her” in reference to the singer but never quite succeeded. Instead, the more unstable she became, the more Winehouse seemed to be replicating Holiday. Like the iconic jazz singer, Winehouse had been advised to stop drinking for the sake of her health, and like Holiday, she refused to comply. In both cases, the decision proved to be fatal.

The parallels between the tragic fates of Billie Holiday and Amy Winehouse are, of course, distinctly troubling. Not simply because, in losing them, we lost two of the greatest voices in jazz, but because both their deaths were partially the result of an invasive media. Looking back, it’s interesting to consider what might have happened to the two singers if they had been accepted on their own terms. Instead, they were held up as examples of degradation and were derided to the point of implosion.

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