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(Credit: John Matthew Smith/Alamy)

The moment Amy Winehouse met her hero Tony Bennett

Amy Winehouse was, first and foremost, a jazz singer. This is a point that can often get lost within the scope of her enormous pop stardom, frequent clashes with the paparazzi, and ramshackle public performances. However, Winehouse was happiest in the smokey club atmosphere that birthed legends like Billie Holliday and Ella Fitzgerald. 

Winehouse’s first album, Frank, was partially named in reference to the legendary crooner Frank Sinatra. That album contains almost none of the pop girl group sensibilities of Back to Black, instead leaning fully into the minor-7th chords and chromatic voicings of traditional 1930s and ’40s jazz music.

Winehouse’s first significant break was with the National Youth Jazz Orchestra. Before her death, she planned on creating a jazz supergroup with Amir ‘Questlove’ Thompson, Mos Def, Raphael Saadiq, and Back to Black producer Salaam Remi. Jazz wasn’t just a dalliance for Winehouse: it ran in her blood.

In March 2011, during the height of Winehouse’s alcohol addiction, she was invited to Abbey Road Studios for a film a duet of the song ‘Body and Soul’ with one of her personal heroes, Tony Bennett. Bennett was recording his Duets II album at the time and had a minor but notable part in Winehouse’s success story. In 2008, Bennett presented Winehouse with the Grammy for Record of the Year for ‘Rehab’. Winehouse was denied a visa to travel to Los Angeles for the ceremony and instead accepted the award at a watch party in London.

“I was playing Royal Albert Hall for two nights … and she came back with her dad, and her boyfriend,” Bennett explained to the Philadelphia Inquirer in 2012. “She said, ‘You know, two years ago, I won a Grammy, and I wasn’t excited about winning the Grammy, but that Tony Bennett was announcing.’ She was a big fan of mine, and I was really surprised, because she [was] so young.” 

There was hesitation in the Bennett camp about inviting Winehouse to take part in the album. Stories of her wayward behaviour, including drinking heavily during recording sessions, were brought up. However, the Winehouse that showed up to these sessions was sober, professional, and, as Bennett recalled, shy and terrified of working with a figure that she truly admired.

“She said she was nervous because she had never recorded a song with someone she considered one of her idols,” he explained. “After running through a few bars, she said she hadn’t recorded for a long time – her only reference to the problems she’d been living through.” 

Still, after a few false starts, the two began to key into each other’s vocal nuances, both of which were rooted in the traditional stylings of the past. Bennett would famously call it “the right way” of singing: never showing off, never using autotune, just playing off the song’s feeling. Despite their nearly 60-year age difference, Winehouse and Bennett sang like they were old souls with decades of history together. 

“She just had the gift of knowing how to sing as good, and was influenced by Billie Holliday, Jackie Washington, Ella Fitzgerald. Her dream was to become very, very famous doing that,” Bennett recalled.

The sessions for Duets II wound up being the final recording sessions in Winehouse’s life. Only four months later, she was found in her Camden flat of alcohol poisoning. She was just 27.

As a final mark on history, though, it’s hard to get any more full circle than to record with one of your heroes in your preferred genre, and Winehouse’s performance with Bennett on ‘Body and Soul’ serves as a reminder of how much talent the oft-troubled star truly had.

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