Just nine years before her tragic death at 27, Amy Winehouse landed a record deal with a risqué jazz number that highlighted her smoky, jazzy vocal prowess and bold, tongue-in-cheek songwriting. Winehouse was unlike anything on the market at the time, and record labels sensed the promise the singer held.
But it was hardly ever as palpable as it was on one fateful day at the London office of Island Records, during which she played the song “I Heard Love Is Blind” for label employees.
Watch Amy Winehouse Win Over Record Label
The Amy Winehouse in the low-quality camcorder footage from the early 2000s is hardly recognizable as the cat-eyed, beehived singer that dominated the pop charts with hits like “Rehab” and “You Know I’m No Good.” But even if her physical appearance was different, Winehouse’s confidence and witty attitude were still apparent. Perched on a plush leather chair with a large dreadnought guitar across her lap, she told the label employees she had written the song she was about to perform in Miami.
“I’m pretty proud of it,” Winehouse said, before moving into the song. The short video, which filmmakers included in the 2015 documentary Amy, displayed the musician’s abilities both as a singer and a guitarist. “I Heard Love Is Blind,” which appeared on Winehouse’s debut album, Frank, is a slinky, clever, and sexy number about how, It’s not cheating. You were on my mind.
Winehouse’s then-manager, Nick Shymansky, called the moment “genuinely jaw-dropping. You could see people at the label thinking, ‘What the f*** is this?’ We’d had quite a lot of rejections and finally we’d signed the deal. It was a really happy time for us” (via Mojo).
But like so many elements of Winehouse’s tragically short life, those “happy times” soon devolved into unrest, tension, and conflict. Her debut, Frank, was hardly a smash success. And Winehouse was more than comfortable expressing her discontent with the label that broke her rejection streak.
How The Jazz Singer “Shot Her Deal Out Of The Sky”
Amy Winehouse was as outspoken as she was talented, which she made incredibly clear when discussing the music industry with the press following the release of her debut album, Frank. “The marketing was f***ed. The promotion was terrible. Everything was [in] shambles,” Winehouse later said, per The Guardian. “It’s frustrating because you work with so many idiots. But they’re nice idiots. So, you can’t be like, ‘You’re an idiot.’ They know that they’re idiots.”
“I hate them f***ers, man,” she continued. “I’ve not seen anyone from the record company since the album came out, and I know why. They’re scared of me. They know I have no respect for them whatsoever.”
Winehouse’s then-manager, Nick Shymansky, admitted that it was difficult to balance his client’s unfiltered attitude with the wishes of the record label. “People were saying they’d never work with her again. Who the f*** did she think she was? You couldn’t have hoped for a better vibe from a label for your artist, and she just shot it out of the sky,” per Mojo.
Despite these difficulties, Winehouse climbed to the top of the charts with later releases, becoming a wholly unique artist in the Top 40 realm. Sadly, her incredibly promising career was cut decades too short when she died in her Camden Square home from alcohol poisoning on July 23, 2011.
Photo by Dan Kitwood/Getty Images
